Capital Investment Advisors

#19 – Revisiting Multiple Streams of Talent with Phil Hendrie

*In the new documentary “Hendrie,” some real heavy hitters, like Bill Hader, Judd Apatow, and Kevin Pollak, all discuss their admiration for Phil’s unique and hilarious creativity. So, we decided this was the perfect time to reintroduce you to the interview he did for our show.*

Phil Hendrie is not retired, not even a little bit. He’s creating as much content as he ever has. But his story still resonates with happy retirees because he had to make a giant change in the middle of his career. In essence, that’s what retirement is—a change. It doesn’t mean you stop doing anything; it means you start doing more of what you’ve always wanted to do.

After taking his radio show from a tiny local station to national syndication, Phil realized the business had changed. It was no longer viable to do comedy on the radio. So, he got creative and transitioned to a daily podcast instead. Because his talent was versatile, he also picked up acting roles and voice work in movies, television shows, animation, and video games. He even retained ownership of his old radio material to repurpose for fans who wanted to listen. Don’t look now, but that adds up to multiple streams of income, and you know we love that on this show!

The bottom line is that even though Phil Hendrie is not retired, his story can still inspire people who want to be. Between that and his comedy genius, this episode is a must-listen!

Read The Full Transcript From This Episode

(click below to expand and read the full interview)

  • Phil Hendrie [00:00:01]:And I also see the rest of my life as being something that you’ve heard a lot of people say this, but I really believe it, like, the best is yet to come. For me, in terms of learning a whole nother craft, learning another level of being an artist and being a performer. So I’ve learned to, no matter what happens, man, it’s an opportunity to make things to springboard even further ahead.Ryan Doolittle [00:00:21]:Phil Hendrie is not retired, not even a little bit. He, he’s putting out as much content as he ever has. The reason why I think he still fits on this show is because in the middle of his career, he had to make a giant change. And I want us all to start thinking about retirement as just that, a change. It doesn’t mean you’re now doing nothing. It means you’re doing more of the things that make you happy. Now, in Phil’s case, he had made it to the top of the radio industry. He had a nationally syndicated show, but at a certain point, it became less and less viable to do comedy on the radio.

    Ryan Doolittle [00:00:58]:

    So he got creative. He started doing a daily podcast instead. And because his talent was versatile, he was able to pick up acting roles in movies and TV shows and animation. He was even able to retain ownership of his old radio material so he could repurpose it to fans who wanted to listen. Don’t look now, but that adds up to multiple streams of income, and, you know, we love that on this show. So the bottom line is that Phil Hendry is not retired, but his story can still be inspirational for people who want to be. And not for nothing, but he’s been a comedy hero of mine for more than 20 years. So it was a real honor to sit down and learn from the best.

    Ryan Doolittle [00:01:41]:

    Do you ever wonder who you’ll be and what you’ll do after your career is over? Wouldn’t it be nice to hear stories from people who figured it out, who are thriving in retirement? I’m Ryan Doolittle. After working with the retire sooner team for years and researching and writing about how they structure their lifestyles, I know there’s more to be learned. So I’m going straight to the source and taking you with me. My mission with the Happiest Retirees podcast is to inspire 1 million families to find happiness in retirement. I want to learn how to live an exceptional life from people who do it every day. Let’s get started. Welcome to the Happiest Retirees podcast. I want to say right off the bat, today’s guest is not retired in any way this is going to be a little different.

    Ryan Doolittle [00:02:28]:

    His name is Phil Hendry. He’s a legend. He was very nice to come on the show, and I think he still fits our theme because he had a big life change. That is inspiring for people who do want to retire because in a way, retirement is just a life change. So he had a big career change, and he had to really navigate that to find happiness and continue with financial success. So, Phil, thank you for coming on the show.

    Phil Hendrie [00:02:54]:

    Thanks, Ryan. Thank you.

    Ryan Doolittle [00:02:56]:

    So, Phil, I’ve actually been dreaming of interviewing you for years. I felt today when I was kind of prepping, I thought, I’ve been prepping for this for a long time. So you’re a radio legend, and your shtick, for lack of a better word, was or is still you are the host, and then you are a fake guest who calls in and the guest says something offensive. And then, at least in the old days when it was live radio, callers didn’t know it was fake and they would call in and be livid. And then you were all the characters kind of playing the game.

    Phil Hendrie [00:03:33]:

    Yeah, that was it in a nutshell. That’s perfectly what you just described there. I was the host, and then I had a phone and people would say, what kind of processing are you using, Phil? It’s just a phone. Just go through a phone box. I know what you’re doing using Dolby. No, no, dude, it’s just a. And I, it was a matter of just, I don’t know how many professionals we have watching this, but it was a matter of, when I was on mic, I was on mic, and when I went to the phone, I just potted the mic down. The phone pot was always, you know, today we have Margaret Gray.

    Phil Hendrie [00:04:03]:

    Thank you very. You know, my husband’s cheating on me and this, that and something else. But I found a lover over here at the Navy base. It’s pretty low class. There’s sea bees. Yeah. But, yes, once a week we meet in the motel. So she would say her know, and then people would be outraged and pissed off and call up and say, I’d like to talk to this lady.

    Phil Hendrie [00:04:24]:

    And that was, in essence, the conceit. Is that the right word of the show? Yeah, that was the conceit of the show. Yeah.

    Ryan Doolittle [00:04:33]:

    Your history a bit. And please correct me because you know yourself better than I know you started.

    Phil Hendrie [00:04:39]:

    I don’t know about that, but go ahead.

    Ryan Doolittle [00:04:42]:

    Well, a long, long time ago, you were kind of just finding your way. You were doing construction down in Florida.

    Phil Hendrie [00:04:48]:

    I think when I was 19. I was 1819. I went to Florida with my buddies. They were building out Disney World. Disney World had just been completed in 71. And we all did what kids do. We got in the car, we drove down there. I got a job with this guy’s father working as a framing carpenter.

    Phil Hendrie [00:05:04]:

    I was a cement finisher, and I knew that I wanted to get into radio. My real goal was to be a writer. And I thought, hey, this is a great job to support myself while I write. That was the initial reason. And so I made a little tape on the advice of a friend, of a friend. His name was, let me just mention him now, Billy Barber at WLF in Orlando. He was the brother in law of one of my construction crewmates. And Bill says to me, well, what you do, Phil, is just take, know cassette tape, read some news, read a couple of commercials if you don’t have an air check, which I didn’t have, and then hoof it around to radio stations.

    Phil Hendrie [00:05:38]:

    And I did.

    Ryan Doolittle [00:05:39]:


    Phil Hendrie [00:05:39]:

    And I thought, well, I’d get a gig in Eustace, or I’d get a gig in Deland or some far flung hick suburb out there. No, I got a job, actually at a station in Winter park, which was a main suburban enclave there in Orlando, at this little station called WBJW at 1440. And there was also a station called WKIS at 740. So one of my friends, Dick Klein.

    Ryan Doolittle [00:06:06]:

    Van Patton. Wow.

    Phil Hendrie [00:06:07]:

    No, I was going to say Dick Van Patton because he said something else. No, he said, you get a kiss at 740, get a BJ at 1440. So anyway, that was the joke there.

    Ryan Doolittle [00:06:16]:


    Phil Hendrie [00:06:17]:

    So I got this gig and immediately started doing overnights on the radio. And I think because I listened to the radio so much as a kid, loved it so much, thought it was just absolutely. It was like one guy creating a movie. That’s what I thought it was, one guy creating a whole mood and movie. And even if he was just going, hey, it’s 75 degrees, this, that, and something else. So I got that gig and an overnight gig. I was a disc jockey, so I really didn’t know all that much. I don’t know how much of this you want me to go into.

    Ryan Doolittle [00:06:49]:

    I want all this. I’m loving this.

    Phil Hendrie [00:06:51]:

    Well, I mean, I wanted to be a radio personality, but I didn’t quite know how to do that. And one of the reasons is because my instincts were so out there that working at a middle of the road music station where we were playing Tony Orlando and Dawn, and we were playing Helen ready and maybe occasionally the Almond Brothers. If it was an acceptable middle of the road type, you know, I would get kind of stepped on if I tried to do any kind of really crazy stuff. So I kind of floated through radio like that, this frustrated disc jockey thing. Again, my instincts are so improvisational and crazy that I think, I thought there was something wrong with me. Maybe when you grow up in the household that I grew up in, and you’re already having self doubts about your quality as a human being because the adults are all just really psycho, and then you have these instincts of character voices and improvisational weirdness that goes well beyond the bounds of human taste. I thought there was something wrong with me, to be honest. Video.

    Phil Hendrie [00:07:55]:

    I thought I needed to walk down the middle of the road a little bit better than I was, and I was know, come on, Phil, you can do this. You can do this the way other guys do it. Well, no, I couldn’t. It’s like this. I can’t do stand up, for instance, stand up comedy. I can’t. All I would do is I got on that stage, would be doing a whole bunch of improvisational character bits and shit that may or may not work, believe I, because I’ve tried.

    Ryan Doolittle [00:08:16]:


    Phil Hendrie [00:08:16]:

    So anyway, I did that. And long story short, Rush Limbaugh got on the air, and I heard what Limbaugh was doing. He was doing in those days, he was doing a lot of humor. He was a right winger. Yeah. He was doing, like, the homeless person report, and he had Clarence Frogman Thomas singing, and he did the EIB Network. He had this environment that he created, the excellence in broadcasting. Well, there’s no such thing.

    Phil Hendrie [00:08:42]:

    And I am the authority. I just thought the character that he portrayed and sort of this marvelous edifice that he constructed, audio edifice, was, and people will say to me, oh, you’re a Rush Limbaugh fan. I said, as an artist, his politics know, and the average person doesn’t get know. I don’t even know if the average broadcaster got it. But I did admire him as an artist at that point. He got rid of all that and just went straight right wing commentary, which I found, frankly, very boring. But EIB, I thought, was hysterical. And I realized something had changed, that talk radio was beginning to open up, and it was opening up to personality driven radio because up to that point, talk radio was news talk.

    Phil Hendrie [00:09:25]:

    So I was, aha.

    Ryan Doolittle [00:09:27]:

    This seems like something I would be.

    Phil Hendrie [00:09:29]:

    Good at, I think, because there’s no music. I don’t have to play any goddamn music. I don’t have to pretend like I like that music. I like the music. Not 50 times a day listening to Touch of Gray by Grateful Dead. So I got this gig at KFI on weekends working for George Angeles, right, in LA. Yeah, I got the weekend shot, but I was doing interviews, and I was just sort of doing this half assed interview show. So I still quite.

    Phil Hendrie [00:09:57]:

    Wasn’t quite breaking out of the mold. I was still kind of trying to. I know what I’ll do. I’ll do talk radio, but I’ll still walk right down the middle of the road and see if that works. Well, no, man, the only thing that’s going to work is when you open up and you just go ahead and give it to them, man, everything you got, and you just go ahead and roll the dice. And if they like it, they like it. If they don’t, they don’t. At least you can say you rolled the damn dice.

    Phil Hendrie [00:10:18]:

    Now you can move on to your next career, which is servicing vending machines or whatever the hell I was supposed to do. So I got fired from that job.

    Ryan Doolittle [00:10:27]:

    I don’t think anyone in radio has ever not been fired is just part of working in kinds.

    Phil Hendrie [00:10:33]:

    They say two kinds of people. Those that have been fired and those that are about to get fired, right?

    Ryan Doolittle [00:10:36]:

    Exactly. Yeah.

    Phil Hendrie [00:10:38]:

    So that’s when I went into a studio here in Redlands, California, for a radio station, KCAL. There’s a KCAL TV station in LA, but there’s also a rock station that I was doing weekends at. And I made this tape, and on the tape, I did this character named Howard Powell. And I just went nuts on this tape, doing all kinds of character voices and doing the show as if these people were real, as if some of them hosted the show. And I put this together in a three or four minute tape, and I sent this to every place I could think of. I knew I was onto something when the great Diane REM, who used to program WCAU in Philadelphia, sent me back a note saying, some of the funniest stuff I’ve ever heard, Phil, I can’t use it. I can’t use it. Because she had this straight laced, middle of the road talk station where everybody was like, now let’s get into city.

    Phil Hendrie [00:11:30]:

    Know this kind of thing, right? Nobody was really looking at radio. Talk radio, I should say, in those days as a full blown, personality driven format. The loop in Chicago had started doing that with Steve Dahl, and Wiod in Miami was beginning to kind of wade into that with Neil Rogers.

    Ryan Doolittle [00:11:48]:

    We’re talking Neil Rogers, right?

    Phil Hendrie [00:11:50]:

    Yeah, we’re talking the early 90s now, okay. But nobody was really doing personality driven talk radio. So I sent this paper around. I thought I was going to have to go to Wildwood, New York. I thought I’d be hired in Northern Canada. I don’t know where I was going to, but I was willing to go anywhere. I’ll go wherever anybody wants to put this on the air. I got hired at a little station in Ventura, KVEN.

    Ryan Doolittle [00:12:11]:


    Phil Hendrie [00:12:11]:

    And this great program director named Rich Galano and a consultant by the name of. Oh, God, Bill. I’m sorry, Bill. Bill McCauley. Bill McCaffrey. Bill McCaffrey is a football player. My good friend Turi Ryder was a prodigy of his. But in any event, I went up there with this goofball show, and Rich Galano, my program director, said to me, you know, this is a small market fill.

    Phil Hendrie [00:12:33]:

    There’s only 600,000 people here. You’re not going to get a lot of phone calls, so just prep your show as if you’re not going to get one phone call. That gave me a lot of permission to do a lot of stuff. And it just so happened the build up to the Gulf War was happening, called Desert ShIELd. The Gulf War began in 91 when we invaded Kuwait. This is Daddy Bush a whole other. And so they were ready made. We weren’t at war yet, so it wouldn’t be tasteless to do shtick about the build up to the, the.

    Phil Hendrie [00:13:04]:

    I think that was my saving grace, to be honest with you, because I got on the air one day after listening to a guy reading two parts of an interview with Saddam Hussein. It was on K ABC Radio. He was reading both parts, and this is what Saddam Hussein said. So I started to do this. You know, it’s perhaps today you’re not supposed to do because it’s considered what usurping? I don’t know. But anyway, I did it. And. Yeah, this is Rajvanin.

    Phil Hendrie [00:13:32]:

    Welcome to KVN. Phil Hendry is not here, but I’m filling in. I want to tell you something about Saddam Hussein. What a good guy he can be. So that’s what I was doing. And the lines lit up, and my engineer was waving at me, or my producer was waving at me, saying, we got a line full of calls. What do you want to know?

    Ryan Doolittle [00:13:52]:

    They want to talk to the fake guy.

    Phil Hendrie [00:13:53]:

    They want to talk to this guy. I said, put him through, man, put him through. And so that’s where it began. And then I started hitting the air with different characters. Margaret Gray is probably the oldest, other than Raj’s character, and that was a female. And I had a call from. Because we live around Navy bases here we have point Magoo. Here we have port WainiMi, the CB station.

    Ryan Doolittle [00:14:16]:


    Phil Hendrie [00:14:16]:

    And this was a young guy says, yeah, I’m here from Missouri and know, just looking around and it’s really nice being here in California and I hope know I meet somebody because I’m kind of, you know. Good luck to you, pal. Okay, thank you. So then I came back with my character. Let’s go to another call. Hi, Margaret. You’re on the air. Yes.

    Phil Hendrie [00:14:33]:

    Phil, the last man you had on the air. Oh, my God. He was devastating. You don’t have a number on him, do you?

    Ryan Doolittle [00:14:39]:

    Or anything that she was interested.

    Phil Hendrie [00:14:43]:

    She was really interested.

    Ryan Doolittle [00:14:44]:


    Phil Hendrie [00:14:46]:

    And that voice was significant because it was an upper chest voice. It was not. A lot of guys do falsetto to do females. We talk like this. Like Monty Python.

    Ryan Doolittle [00:14:55]:


    Phil Hendrie [00:14:55]:

    Excuse me.

    Ryan Doolittle [00:14:56]:

    Is that it? Yeah, that reminds me.

    Phil Hendrie [00:14:58]:

    But that’s not really a realistic female voice. A realistic female voice is. You have to go in the upper chest up here and affect. And so much of this woman, this character was based on my mother is like, they’re in my head. Just started feeding my mom through this character.

    Ryan Doolittle [00:15:13]:


    Phil Hendrie [00:15:14]:

    And it’s amazing how easily you can affect a female voice if you know the character. Not just how to do a high pitched voice, but what’s the character saying?

    Ryan Doolittle [00:15:25]:

    Exactly? And just quick Sidebar. I read the biography you wrote about fake Margaret Gray, and it’s breathtaking how well you know this fake character. I mean, you know her better than I think I know me. And the great writing teacher, Robert McKee said that about Humphrey Bogart and Casablanca. He said, I know Rick better than I know myself. He’s always. I’m kind of iffy. He’s always who he is.

    Ryan Doolittle [00:15:51]:

    You know what I mean?

    Phil Hendrie [00:15:52]:

    I love it. I can dig. I see what you say. Well, yeah, here’s the thing. In acting, they always tell you, at least I learned in the acting classes that I took. Write out the biography of your character, and I’m not that disciplined. So I just perform the character and the biography begins to come to me. I can do about two minutes of a character, and I’ve got a pretty good biographical sketch of that character where they’rE know, are they married? Are they not? Do they have kids? This kind of thing? So Margaret, all of a sudden, she’s know out there.

    Phil Hendrie [00:16:24]:

    She was my mom. So I live in Santa Monica, which is not the most high. Santa Monica is a beautiful city, but it’s not what I call. It’s not?

    Ryan Doolittle [00:16:32]:


    Phil Hendrie [00:16:33]:

    But, you know, I live there with my husband Frank, and I’ve got my ear to the ground out there. She’s kind of a gadfly. Yeah. So that’s how these characters are built. And the key was deliver them as realistically enough so that callers will want to talk to them. Make sure the topic is very organic. Make sure the topic is, what’s the word? Reactive. And deliver it as realistically as possible.

    Phil Hendrie [00:16:57]:

    So we found over the course of many years, I would say the show was totally at its strongest. The last year I was doing the show at KFI, 2005, 2006. Last two years, we had it down, man. We knew topic. We knew what would resonate with the audience and what got calls. Realistic calls.

    Ryan Doolittle [00:17:20]:

    Yeah. I can’t remember the exact year. Maybe 2004 or something. But you had a bit where Margaret was being interviewed, and her husband, Frank Gray, was in the back, and she wanted a drink, and you could hear him. And you’re really good at throwing the audio. So it’s like lower ambience.

    Phil Hendrie [00:17:41]:

    Yeah. You pull the phone away and closer.

    Ryan Doolittle [00:17:45]:

    Yeah. So in the background, I can just kind of hear him say, where’s the ice? And then you hear Margaret say, where it’s been years. And I’m like. I was, like, listening to my parents have a conversation. I wrote into you asking about that specific comedy choice, and you answered it on the air, and it was just a great day for me.

    Phil Hendrie [00:18:06]:

    Oh, cool. I’m glad that I answered that. Yeah, ambiance does a lot in terms of the character voice itself, too. You can simply. This, the bottled water guy is here. Put it over there. This is Sid. How are you doing, Sid? I’m great.

    Phil Hendrie [00:18:25]:

    And if you got him, he sounds like a real guy. Back know, Sid putting the bottled water in. And it’s funny how many of those characters I do sound really know, like J. Sam. Subcommander Gleason, what do you think? I’ll do it right away. Okay. Good job.

    Ryan Doolittle [00:18:41]:

    He’s just an idiot. Yeah.

    Phil Hendrie [00:18:44]:

    All kinds of wonderful little things you can do, like ambient changes. Tells you they’re in a different place. And all you have to do is move the phone from here to here. And it sounds like, well, we’re not here anymore. We’re in the car with Frank. Frank’s over there in the car, or Frank’s out on the driveway or something like. Yeah.

    Ryan Doolittle [00:19:03]:

    And you’re doing a whole sound design. Just live by yourself.

    Phil Hendrie [00:19:09]:

    It’s an instinct, and it’s probably one I had. I don’t know if I was born with it, but it’s an instinct, man. It’s an instinct. What’s going to work. I was so in love with radio as a kid. I mean, listening to it and analyzing it and studying it and listening to it at night and the audio part of it. I love TV. I watch TV all the time, and I love the actors, and I loved all the characters that I saw.

    Phil Hendrie [00:19:29]:

    But radio was a place that you could control the whole universe. One guy. And maybe that’s. Maybe that’s. Know, maybe it’s just that Phil, Henry, I cannot be bothered with other actors. All you guys just get out of my life. Me, I’m the one guy. But how do I take that and translate that into a bigger and wider audience? So, I don’t know.

    Phil Hendrie [00:19:49]:

    I do my podcast. Obviously, we don’t do the radio show anymore because radio doesn’t really exist anymore, man. Not in the sense that we used to do it.

    Ryan Doolittle [00:19:57]:

    That’s why I thought you could fit on this show even though you’re not retired, because. And I don’t remember the year, but. So you were getting into it, but you made it to KFI, and then you went national. I think it’s premiere radio.

    Phil Hendrie [00:20:13]:

    Yeah, I went national with Premiere radio from 99 through 2006. I had interest from casting directors and some people producing TV shows, so I started to kind of drift into the acting thing. I had done a couple of shows while I was on the air. At premiere, we had done a show called Teachers for NBC. I had produced two pilots.

    Ryan Doolittle [00:20:31]:

    Phil at the Gate, I think was one.

    Phil Hendrie [00:20:33]:

    Phil at the gate was one. And then another one called Phil Henderson was an animated show for Steve Levitan. And now there were a lot of people auditioning me for different shows, and I thought, well, this is. I’ll do this. Then I made the biggest mistake of my life. And you know what? I shouldn’t call them mistakes. They’re all, you know, dude, I wouldn’t be who I am today, and I wouldn’t be headed toward the good things that I’m headed toward if I didn’t make these mistakes, I don’t think. But I signed another radio deal with TRN.

    Ryan Doolittle [00:20:57]:


    Phil Hendrie [00:20:58]:

    Yeah, with TRN.

    Ryan Doolittle [00:20:59]:


    Phil Hendrie [00:20:59]:

    So I had this momentum, and I got hired on a bunch of jobs. I got hired to do some recurring stuff on a show called the Unit.

    Ryan Doolittle [00:21:06]:

    Yeah, that was a David Mamet show, wasn’t it?

    Phil Hendrie [00:21:09]:

    Yeah, man, I worked for David Mamet. He came in and directed one of the episodes. I’m like, wow, he goes, hi, I’m Dave. How you doing? Hey. So where do you see your character? Where do you see your character in this scene? Well, I don’t. I think he’s okay. He’s sitting. Yeah.

    Phil Hendrie [00:21:21]:

    Okay. Have him sit down over there. That’s great. Now, you know, this is the great playwright David Mammond. He sounds like out of a pool. Me and I wrote some extra stuff for you, Phil. He wrote a whole scene for me. Wow.

    Phil Hendrie [00:21:34]:

    Yeah. In fact, when I was leaving that day, one of the Pas came up to me and said, do you want the script? Because he wrote this scene for you? I said, yeah, let me have.

    Ryan Doolittle [00:21:44]:


    Phil Hendrie [00:21:44]:

    I didn’t have him autograph it. That would have been a little too weird. But did you ever see him drinking.

    Ryan Doolittle [00:21:49]:

    A cup of coffee and say, put the coffee down. Coffee is for closers.

    Phil Hendrie [00:21:54]:

    Should have been. That’s funny, man. Because I’m trying to learn a scene from that very Glenn Ross.

    Ryan Doolittle [00:22:03]:

    Yeah, yeah.

    Phil Hendrie [00:22:04]:

    And I’m trying to memorize this scene because I want to use it for an audition for a theater group in. But so what’s the character that I’ve chosen? Jack Lemon’s character, Levine and Mamet writes like, this is how Mammoth writes. Hold on for a second, because I’m going to tell you right now, I was getting ready to do the Dutch. No, all of this. How the hell.

    Ryan Doolittle [00:22:26]:

    I’ve been working script.

    Phil Hendrie [00:22:27]:

    It’s in the script, brotheR. It’s in the script, man. Yeah.

    Ryan Doolittle [00:22:30]:


    Phil Hendrie [00:22:30]:

    So I’ve been working on that for about five years. So I did all that, and then I was reading for things, and then I signed. Then this radio opportunity came up that the manager I had at the time knew the people that ran that network, and I said, you know what? I love acting, but I got to sit on my ass between gigs waiting for the phone to ring from your agent. And if I’d been more disciplined, I probably would have gone out and took an acting class or read a lot of plays. I don’t know what. But I wanted to create. And this radio gig came up. So I took this gig, and I thought I would do this.

    Phil Hendrie [00:23:06]:

    I thought I would have humor, but also do serious political commentary. I was going to kind of evolve whatever it was Phil Hendry was trying to do, which didn’t last very long. I eventually just went back to doing straight character voices. But this gig was so horrible. I didn’t like it because I had it for three years, and they had an option for another three, and they wouldn’t let me out of the deal. So I basically spent six years in that, you know, you live and you learn, man. And I was able to get a little bit of. I got some good shows out of also.

    Phil Hendrie [00:23:39]:

    The other thing, Ryan, is I also realized what was I really wanted to do. I can’t keep beating this horse to death. By the end of this gig, there was just no money left in radio. I mean, there was no real syndicator left. It was all people. I don’t know what they were doing, man. Specialty acts, right wing stuff.

    Ryan Doolittle [00:23:57]:


    Phil Hendrie [00:23:58]:

    Michael Savage had taken off. Laura Ingram was taking off. This kind of radio I didn’t want to have anything to do with. Not that I’m not commenting now politically. I’m just saying I’d want to do a talk show. Yeah, I want to do a.

    Ryan Doolittle [00:24:13]:

    Have. And we’ll get into this. One of your. I’d call it a stream of income now is you have a backstage pass where you can.

    Phil Hendrie [00:24:20]:

    Yeah, we have our website.

    Ryan Doolittle [00:24:23]:

    You want to say the website.

    Phil Hendrie [00:24:25]: Yeah. Okay.

    Ryan Doolittle [00:24:29]:

    And I had a backstage pass, and so I got to watch you prep for your show, and I do remember during that time, you seemed a lot angrier than you do now.

    Phil Hendrie [00:24:42]:

    For sure, man.

    Ryan Doolittle [00:24:43]:


    Phil Hendrie [00:24:45]:

    I was under a lot of pressure, but what I was able to do is I got the rights to my show from iHeartRadio. Back then, it was clear Channel.

    Ryan Doolittle [00:24:53]:

    Yeah. Okay.

    Phil Hendrie [00:24:54]:

    And I got rights to a lot of my materials, so I was able to take all of those shows that I had from Cox in Miami, my Miami show at WIOd, and put that on my website. And then I decided, well, I’ll produce some new shows that will be podcasts, because that’s what’s going on now.

    Ryan Doolittle [00:25:08]:


    Phil Hendrie [00:25:09]:

    And I’ll just let my instincts run wild in terms of character and see where it takes me. And that became the Daily Phil Henry show podcast, which exists to this day, although it’s evolved and changed over time. And I’ve had people tell me they think it’s funnier than the stuff I did when I was on the radio. I don’t know whether I agree with that 100%, but I think there are times when, yeah, I laughed my ass off more than I did, because when I was listening to my radio show back, I’d be going, oh, I hope people call. Please call. Please. Let’s get some call. Whereas just kind of letting it go.

    Ryan Doolittle [00:25:40]:

    Felt better in terms of the career change you made that. I mean, from where I’m sitting, you look happy. You say you’ve got, financially, you’re doing great.

    Phil Hendrie [00:25:50]:

    I’m wealthy beyond all measure. I’m fine. I’m living.

    Ryan Doolittle [00:25:57]:

    And our flagship podcast is called Retire Sooner. So our boss, essentially Wes Moss, is always saying you need multiple streams of income as you enter certain stages. But you seem like you do because you have the podcast ad revenue or maybe also the podcast one distribution deal. I don’t really know how.

    Phil Hendrie [00:26:18]:

    Well, no, my subscription base is the money. The ad revenue from podcast one, I’d say is kind of. I wouldn’t say it’s the main revenue stream from the podcast, but it’s an added amount of money. And then, like I say, voiceover and camera acting and residuals from all of.

    Ryan Doolittle [00:26:39]:

    That, you’ve done King of the Hill. You did Modern Family. You were the voice of intelligence on Team America, which is the South park guys.

    Phil Hendrie [00:26:50]:

    Yeah, I just got done doing a video game called. So, yeah, I’m on video games now. Wow. There’s a cat that I used to work with, Steve Downs. Steve and I worked at K West. He does a main voice on Halo. He’s like the chief or something. On Halo.

    Phil Hendrie [00:27:10]:


    Ryan Doolittle [00:27:11]:


    Phil Hendrie [00:27:12]:

    I had no idea, man. I think Steve’s with his wife. He and his wife live in Chicago. He was our program director and afternoon drive guy at K West, but now he’s so. Games. Video games. Yeah, it’s heavy.

    Ryan Doolittle [00:27:24]:

    Yeah. And I think a lot of people would remember you from this is 40, because Paul Rudd slams his bike into your car and then.

    Phil Hendrie [00:27:32]:

    Yeah, but I mean, king of the hill, Futurama, the replacements, the 7D. I’d have to actually put. Let me just pull up my IMDB.

    Ryan Doolittle [00:27:41]:

    No, your resume is so long, we don’t even have.

    Phil Hendrie [00:27:44]:

    Yeah, I don’t have the time right.

    Ryan Doolittle [00:27:45]:

    Now, but we have a lot of listeners in Atlanta. That’s where I mentioned our Wes Moss. He actually has a radio show on WSB. I don’t know if you ever worked for them.

    Phil Hendrie [00:27:55]:

    I was on WSB. I was on WSB in 1992.

    Ryan Doolittle [00:27:58]:


    Phil Hendrie [00:27:59]:

    Yeah. I did ten to two at night, and then on Saturday night, I had a Saturday night show. It was the Steve Warnell Show. That was an early carnation incarnation, I should say, of Steve Bozell. So on Saturday night, WSB with Steve Warnell. How you doing? It’s Steve Warnell in the Daytona 500 is coming up. The greatest spectacle in race. I did 4 hours of this bull crap.

    Ryan Doolittle [00:28:20]:

    4 hours as the character.

    Phil Hendrie [00:28:22]:

    As this character. In character.

    Ryan Doolittle [00:28:23]:

    My God.

    Phil Hendrie [00:28:24]:

    In character. Yeah, I had a blast, and I’d get off the air, and I’d go to my favorite bar in Buckhead called the Churchill Downs and just get hammered. And everybody up know, had a blast, had a good time in Atlanta.

    Ryan Doolittle [00:28:37]:

    Okay, so before you left radio and you sort of plunged into podcasting and more acting voice work, and did you have, like, a plan and a purpose?

    Phil Hendrie [00:28:49]:

    I did not. There was a lot happening in my life at that time. I had a marriage that was going south that was taking an awful lot of emotional energy. But what I thought I would do, I was on a show called Teachers. It was on NBC, and we had six episodes in the spring. And I worked with great people like Matt Winston was there and Kali Roka was there and Sarah Alexander and just really great actors.

    Ryan Doolittle [00:29:16]:

    Justin, or someone that’s from the hangover, right?

    Phil Hendrie [00:29:19]:

    Oh, Justin Bartha. Justin Bartha. And we had Matt Tarsus, who was our producer, and I was kind of hoping, as everybody does, that it would get picked up for another season. And by that point, I think I was ready to just leave radio, man. I was burning out because doing that kind of a show, and I’d been doing it for 16 years, you have to literally take a blank canvas every day and paint some kind of a masterpiece. What kind of a character are you going to do today, Phil? And how many people are going to call up and be fooled by it? It was getting kind of crazy. So all I knew was that I think I’ll segue into acting, camera acting, and see where it goes from there. And that’s exactly what I did do.

    Phil Hendrie [00:30:04]:

    Like I said, I got this job recurring on the unit. I got hired for a couple of pilots. One really fun pilot was based on talk radio. I played a Rush Limbaugh character named Rude Carnahan, who actually broke into doing character voices on the air. And that pilot got produced, and we thought for a while that was going to get picked up because CBS had been evidencing some interest in, you know, you learn very rapidly what that whole game is about, man. So while I was doing some acting jobs and I was doing some voiceover work, I wasn’t working enough for my taste. So I got back into this. I signed this other radio deal that was really a revenue sharing deal that went three years longer than I thought it would.

    Phil Hendrie [00:30:50]:

    And it takes a lot of the juice out of what you’re trying to do elsewhere, especially in the acting field. Although I still was doing pilots, I did one with Justin Burbiglia, who’s a very funny comedian, had a pilot with the CBS. I played his dad.

    Ryan Doolittle [00:31:03]:

    Wait. Is he related to Mike Burbiglia?

    Phil Hendrie [00:31:05]:

    I’m sorry, Mike Berglia. Did I say Mike Berbiglia? Yeah, it was Mike. Okay, sorry, Mike. But I’m JustiN Henry, so that was a lot of fun. But you’re also doing this radio show, and you’re trying to work out how you can do a radio show in an ever constricting atmosphere. The money ain’t there anymore. Now I’m dealing with a syndicator out of town. I’m dealing with a screener that’s remote.

    Phil Hendrie [00:31:31]:

    I can’t just walk into the next room and give instruction to my screener and how. No, they felt they knew how to screen my show. We feel like we know exactly how to screen your show, Phil. Well, no, you don’t.

    Ryan Doolittle [00:31:40]:


    Phil Hendrie [00:31:41]:

    So I was fighting that bloody battle and eventually morphed. When that contract ended, I morphed everything into a podcast, everything into a. At first, a three hour. You remember the old app tune in? Yeah. So at first, we were doing a three hour tune in show. Yeah. And that was nuts. Lots of work.

    Phil Hendrie [00:32:01]:

    And I realized I don’t have to work that hard, man, because people aren’t listening to this content the way they used to. They’re not listening to it like they did on the radio. They’re listening. They’re downloading it and listening at their leisure. And the attention span doesn’t need to be 3 hours. So I began to cut it down in size. We just put it on our platform and just let people download it from there. We got a great partner in Sideshow Network, and then we segued over to podcast one, in terms of the revenue platform, any advertising revenue, and kind of learned the ropes that way, man, all the while still pursuing whatever kind of voiceover and camera work I could do.

    Phil Hendrie [00:32:38]:

    I mean, I did. Those were the days when I was still doing Futurama was still, I think, or King of the Hill was still being produced. And then I got, like, camera gigs on shows like New Girl, and I got an episode of Modern Family.

    Ryan Doolittle [00:32:51]:

    Young Sheldon, maybe. Young.

    Phil Hendrie [00:32:53]:

    Yeah. Young Sheldon did a voiceover in young Sheldon, and kind of feeling my way with that. But if you’re going to be an actor, you got to really, sooner or later, really devote serious time to it, to become a good actor and not just be the guy they hired to play the disc jockey or the guy they hired to play the general manager of the radio station. That kind of thing.

    Ryan Doolittle [00:33:11]:

    That only takes you so far. Yeah, exactly. And I had this sense because I follow you on social media. But you seem happy. How have you pulled that off?

    Phil Hendrie [00:33:24]:

    Because I’m miserable and I want to kill every day. I don’t know. Well, I’m a Nisharan Buddhist, man. I might as well just kind of throw it out there. I’m not trying to convert anybody. Please. But early on in my life, I was interested in spiritual things, and I did. TM, which I wouldn’t call.

    Phil Hendrie [00:33:42]:

    TM is not really spiritual. TM is about unstressing the nervous system. Transcendental meditation.

    Ryan Doolittle [00:33:46]:

    Transcendental meditation.

    Phil Hendrie [00:33:47]:

    Meditation, yeah. But I got into Nishan, Buddhism, and basically, I’ll just say this. The purpose of religion is to be happy. Nobody had ever said that to me before. They said, what’s the purpose of religion? To be happy. Okay, I’ll take that. That sounds pretty good.

    Ryan Doolittle [00:34:02]:

    Who doesn’t want that? Yeah.

    Phil Hendrie [00:34:04]:

    So what I do with my life now is I see everything as an opportunity. I see everything. Even if it’s a mistake, I see it as a stepping stone to the right thing to do. Everything that happens to me is a forward progress. And you just don’t ever give up on anything, man. You just don’t ever, ever give up on anything, because you will conquer. It’s when you stop, that’s when you start to slide back, and you don’t win. And it’s proved out.

    Phil Hendrie [00:34:34]:

    In my life, in the middle of this pandemic, I met a woman who I’d already met in Florida in 1994, Jackie Bales, who’s now my girlfriend. And she’s one of the better things that’s happened in my life in the middle of the whole world shutting down. And I’ve also been able to make more and better professional contacts with people, and I’ve seen my business flourish. Gosh, I live 100 yards from the ocean. I guess that can’t possibly that be that bad. And I also see the rest of my life as being something that you’ve heard a lot of people say this, but I really believe it. Like, the best is yet to come. For me, in terms of learning a whole nother craft, learning another level of being an artist and being a performer.

    Phil Hendrie [00:35:16]:

    So I’ve learned to, no matter what happens, man, it’s an opportunity to make things, to springboard even further ahead.

    Ryan Doolittle [00:35:27]:

    In a way, instead of slowing down, you’ve found.

    Phil Hendrie [00:35:34]:

    Able to. I would say the biggest difference is that there’s a guy that I follow on Instagram. This poor boy was born with a very terribly disfigured face. His name’s John O. Do you follow this kid at all. He’s on Instagram. He’s a motivational speaker. Oh, wow.

    Phil Hendrie [00:35:52]:

    He goes out into public. He was born with this face that’s pretty badly disfigured. It’s not horrible. But he said something that kind of resonated with me. He said, don’t say anything to yourself that you wouldn’t say to a five year old if you’re going to put yourself down. Would you say that to, like, a five year old kid? Would you say that to your five year old self? How would you address yourself as a. And as sort of touchy feely and Namby Pamby as that sounds and probably totally out of character for a guy like Phil Henry. That means something to me, because what I did through most of my life is just wag the finger at myself and say, here’s another screw up.

    Phil Hendrie [00:36:32]:

    Look at how you messed this one up, man. Look at how you messed that one up. Look at all this opportunity and you didn’t do this. Now I just tell myself, all right, man, well, let’s try it better next time. You know, actually, there’s this. We can learn from that. And there’s that. We can learn from that.

    Phil Hendrie [00:36:44]:

    And I was just talking to Jackie. She was telling me she’s selling her house. And she said, my buyer is cool, but the person buying his house, their financing fell through. And I go, shit. She goes, but you know what? It bought me a week because the financing is going to come through, but it’s going to be seven days. And that whole week is going to give me time to do more here and do more there and do more there. So I’m thinking, yeah, what apparently was a really horrible sounding thing, financing falling through. Maybe your house isn’t going to sell.

    Phil Hendrie [00:37:16]:

    Maybe actually it is going to come through. It’s going to be a week later, and it’s going to give her more time to do the shit that she needs to do with the house. And that’s how I look at things, man. What can I take from this and make it bigger so it’s like a.

    Ryan Doolittle [00:37:29]:

    Glass half full whole, sort of.

    Phil Hendrie [00:37:30]:

    Well, but I don’t look at it that way. All I’m saying is, I don’t know, man. I haven’t stopped doing anything that I like to do, and I haven’t stopped pursuing these dreams. Although the dream is not the. It’s never been my dream to be an actor. It’s been my intent, because that’s what I’ve been doing for most of my life on the radio and doing what I’ve been doing. So.

    Ryan Doolittle [00:37:52]:


    Phil Hendrie [00:37:53]:

    To work more steadily on camera, to work more steadily in theater, to actually make a living. The majority of my living doing that would be, I’d say, my goal for the next 60 years.

    Ryan Doolittle [00:38:05]:


    Phil Hendrie [00:38:06]:

    Yeah. And then see what happens after that.

    Ryan Doolittle [00:38:10]:

    It’s funny when you say how hard you are in yourself. I find that when I think about how I am with myself, I would never treat someone else that way. I’m far for sure.

    Phil Hendrie [00:38:21]:

    That’s the whole thing. Yeah, that’s the whole thing. I think that’s what his point was. You’re not going to say that to a kid. Why would you say it to yourself? Yeah, so I spent most of my life doing that. I think because of our background, man. I don’t know what kind of home life you come from, but I came from a home that was extremely dysfunctional. That’s a good word, isn’t it? Dysfunctional? You don’t have to say violent things, being thrown through doors and shit.

    Phil Hendrie [00:38:50]:

    And I came out of that experience with a really low opinion of myself. I wouldn’t say I didn’t think I was a bad person. I just didn’t have a whole lot of self esteem.

    Ryan Doolittle [00:38:59]:


    Phil Hendrie [00:39:00]:

    And you have to scrap and fight and battle for that in life. And along the way, you meet people who help you.

    Ryan Doolittle [00:39:08]:

    I heard someone say, I wish I could remember who said it, but they said, all the wrong people hate themselves. So you see these guys who really behave terribly, they look in the mirror and think, I’m pretty awesome.

    Phil Hendrie [00:39:22]:

    I’m a pretty cool guy. Yeah.

    Ryan Doolittle [00:39:23]:

    And then these really nice people who are so hard on themselves.

    Phil Hendrie [00:39:28]:

    It’S that kind of what they have. Psychopaths, of course, have no conscience about things, so they’re naturally going to go, yeah, I’m okay.

    Ryan Doolittle [00:39:34]:

    Right. Like Bobby Dooley.

    Phil Hendrie [00:39:36]:

    Yeah. She’s very psychic. Yeah. Bobby’s very sociopathic.

    Ryan Doolittle [00:39:39]:


    Phil Hendrie [00:39:41]:

    Your sons just spray painted swastikas on a know. It’s like, don’t you get?

    Ryan Doolittle [00:39:51]:

    You know, she. She’s the president of the association.

    Phil Hendrie [00:39:56]:

    And the scary thing about people like that is they have a certain charm. People are attracted to their confidence. They’re attracted to their. You’re an original thinker. I like, you know.

    Ryan Doolittle [00:40:08]:


    Phil Hendrie [00:40:10]:

    And Bobby Dooley is based. A little bit of hers based on my know, because my mother could be looking at you, my mom could be looking at me, and I could be telling her, Mom, I’ve just been nominated for the Nobel Peace Prize, and she’d be looking at my shoes. You’re wearing that to the thing. Yeah, that kind of shit.

    Ryan Doolittle [00:40:28]:


    Phil Hendrie [00:40:31]:

    But here’s the cool thing about all of that. I love my mother. I love my father. I forgive them both. They had hard lives. They came up at a time when life was hard, man. They were both teenagers at a time when the world was spiraling into another World War. There was the Depression.

    Phil Hendrie [00:40:46]:

    My mother’s home life was terrible. My dad was adopted. They were not good parents. But you know what, man? I love them. I forgive them, and I understand them, and I still think of them as my friends, and I appreciate the stuff that they did know. My father picked up and brought the family to California. That alone, he should be my hero, for I was raised in California, not Canada, not Toronto, Canada. I love Canada, don’t get me wrong.

    Phil Hendrie [00:41:11]:

    But it’s warmer, you know? So they did that, and they made a home, and they tried the best they could. And while we were all very scarred by our childhood, my sisters and I, who I still have dinner with, we have forgiven those people. That’s what you got to do, man. You can’t be angry at anybody. You can’t hate anybody.

    Ryan Doolittle [00:41:33]:

    No. It ends up hurting you if you do.

    Phil Hendrie [00:41:35]:

    IT really does. People don’t really understand that.

    Ryan Doolittle [00:41:37]:

    Well, what do you mean, it hurts you?

    Phil Hendrie [00:41:39]:

    It feels good sometimes just get angry at somebody. Yeah, but you can’t live your life like that, man. You can’t incorporate that and make it part of your being. Yeah, I’d say that that’s one of the great things that’s happened to me in the last several years, 20 years.

    Ryan Doolittle [00:41:54]:

    Well, I’d love to keep going, but I wanted to ask if you want to tell us where people can find all your different pursuits.

    Phil Hendrie [00:42:02]:

    Well, yeah, you can find That’s my website, and that’s where my archive is. Like, 60,000 people think I’m exaggerating, but we think it’s around 60,000 hours of the radio and the digital stuff that we’ve done, it goes back all the way to Miami, 1994. So we’re talking almost 30 years of material on the website, and we still have more. I got, by the way, here’s my buddy, Dan Jackson. Danny, thank you. This is the thumb drive that Dan sent me of some of my shows from KFI, early days of KFI radio that I have yet to upload to the site. So we have to get this uploaded, man.

    Ryan Doolittle [00:42:39]:

    So new material is coming.

    Phil Hendrie [00:42:41]:

    New material, man. Yeah, he has notes here, Phil. Dan Jackson Tapes, Volume one of two. This is 1997. And 1998 KFI archive.

    Ryan Doolittle [00:42:52]:

    So, wow.

    Phil Hendrie [00:42:53]:

    We got more that we’re loading in there. And I announce whatever it is we’re doing. My IMDB is at IMDB. You can check out the stuff that I’ve done if you want to go and look at some of the reruns of that stuff. And we’re always constantly on social media announcing the things that’s coming up, although I am kind of shy about that stuff. I did an episode of Grace and Frankie, which was a personal moment of Pride for me because I was in a scene with Martin Sheen and Sam Waterston, and it doesn’t get any heavier than those two cats, in my opinion.

    Ryan Doolittle [00:43:22]:


    Phil Hendrie [00:43:23]:

    And where a lot of actors would say, I just did a scene with Martin Sheen on Martin. Great. I kept my mouth shut about it, and I don’t know why. I didn’t want to sound like some lame ass. You know what? I just. Yeah, I just let it slide, man.

    Ryan Doolittle [00:43:37]:

    You can’t be too much of a fan or you come off like I did today talking to you. You know what I mean?

    Phil Hendrie [00:43:42]:

    Well, I don’t know. Yeah, but we’re all over the place, man. Like you said, this is 40 and some other movies. Team America. We just posted about Team America because I think it’s the 30th. No, the 25th anniversary. That sounds about of Team America.

    Ryan Doolittle [00:43:57]:


    Phil Hendrie [00:43:58]:

    And so there was a big social media posting on that, which I reposted because I did a couple of voices on that in that movie, intelligence and a terrorist.

    Ryan Doolittle [00:44:07]:


    Phil Hendrie [00:44:07]:

    So follow us on Facebook. Phil Hendry fans phans and spell your.

    Ryan Doolittle [00:44:13]:

    Last name, because some people spell it the wrong way.

    Phil Hendrie [00:44:15]:

    H-E-N as in Nancy. D as in David. R-I-E. Phil Hendry fans. P-H-A-N-S. I’m also on X at Real Philhendry, although that place has just gotten really weird. We’re on Instagram. Just Philhendry on Instagram.

    Ryan Doolittle [00:44:29]:

    Well, Phil, thank you so much for coming on the happiest.

    Phil Hendrie [00:44:32]:

    Thank you, Ryan. And let me just let everybody know. Ryan was so patient, was late. I thought it was at 01:00 and I was, like, a half hour late. And thank you, brother, for hanging in.

    Ryan Doolittle [00:44:41]:

    You’re well worth the wait.

    Phil Hendrie [00:44:42]:

    Oh, thanks.

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