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Lynn Ho
This is an iHeart podcast.
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Wilmer Valderrama
Get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconic sitcoms of all time? You get Desi Arness on the podcast starring Desi Arness and Wilmer Valderrama. I'll take you on a journey to Desi's life. How he redefined American television and what that meant for all of us watching from the sidelines, waiting for a face like ours on screen. Listen to Starring Desi Arnaz and Wilmer valderrama on the iHeartRadio app, Apple Podcasts or wherever you at your podcast.
Kyle McLaughlin
Hey, I'm Kyle McLaughlin. You might know me as that guy from Twin Peaks, Sex and the City, or just the Internet Stand. I have a new podcast called what Are We Even Doing? Where I embark on a noble quest to understand the brilliant chaos of youth culture. Each week I invite someone fascinating to join me to talk about navigating this high speed rollercoaster we call reality. Join me and my delightful guests every Thursday and let's get weird together in a good way. Listen to what Are We Even on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Norah Jones
Hey, I'm Nora Jones and I love playing music with people so much that my podcast called Playing along is back. I sit down with musicians from all musical styles to play songs together in an intimate setting. Over the past two seasons, I've had special guests like Dave Grohl, Levy, Rufus Wainwright, Mavis Staples. Really too many to name. And there's still so much more to come in this new season. Listen to Nora Jones is playing along on the iHeartra app, Apple Podcasts, or wherever you get your podcasts.
Jim Florentine
Thanksgiving isn't just about food.
Kyle McLaughlin
It's a day for us to show.
Cal Penn
Up for one another.
Jim Florentine
It's okay not to be okay sometimes and be able to build strength and.
Cal Penn
Love within each other.
Kyle McLaughlin
I'm Elliot Connie, host of the podcast Family Therapy, a series where real families come together to heal and find hope.
Lynn Ho
I've always wanted us to have therapy. So this is such a beautiful opportunity.
Kyle McLaughlin
Listen to season two of Family Therapy every Wednesday on the Black Effect Podcast Network, iHeartRadio app, Apple Podcasts, or wherever.
Jim Florentine
You get your podcasts.
Lynn Ho
Comedy Saved Me.
Jim Florentine
Yeah. Cause I grew up a family of seven, Catholic, you know, so just, you know, I just think the whole, the whole ball busting, you know, with that's. We're just pulling pranks on each other and just, you know, you had to have tough skin hanging out in the neighborhood with all the neighborhood kids. And it was one big, like, big community and stuff. And that's just the way I was raised, is just being like a wise ass.
Lynn Ho
I'm Lynn Ho, the host of the Comedy Saved Me podcast, the podcast that explores the world of comedy, the masters behind the work, and the true power of comedy in our life. Now, if you like this podcast, you might like another one called Music Saved Me that I host as well. And you can find that wherever you get your podcasts. Now. Today, my special guest is a true original. His name is Jim Florentine. And Jim is known for his outrageous prank calls on the Howard Stern show and his hilarious work on one of my favorite shows. But beyond all the laughs, Jim's journey is a testament to how comedy can be a really creative outlet and a lifeline for many of us. From his early days as a radio DJ to becoming a stand up comic, Jim has used humor to tackle life's challenges. Jim shares stories of his career, talks about the therapeutic power of comedy, and reveals how his unique blend of humor has helped him through very tough times. Jim Florentine, welcome to Comedy Saved Me. It's great to see you.
Jim Florentine
It's great to see you, Lynn. Wow, what an introduction.
Lynn Ho
I'm like, damn, I left out movies, television, all that other. I mean, you've done it all pretty much.
Jim Florentine
Yeah, I got lucky here and there.
Lynn Ho
I don't think so, but we can discuss that. What insp. Let's start with what inspired you to pursue a career in comedy and how did your early experience shape your, dare I say, sarcastic style?
Jim Florentine
You know, I always. I was always a music guy. I was always in the music, and all my friends were in bands growing up, and that's what I wanted, to be, a rock star. I just didn't have the talent. I tried. I went for singing lessons. I tried to play guitar. I was a lefty. All my friends like, well, if you could play righty, I could teach you. I'm like, I can't play righty. So I. And I was Like, I want to be on stage, because I just love that whole thing. And then when I saw, you know, like, Andrew Dice Clay, Sam Kinison, and all of a sudden, comedians started being, like, kind of like rock stars. And I was always, always into comedy. I used to watch Richard Pryor, Rodney Dangerfield and stuff. And then I just went to an amateur night one night I was doing radio, and they were telling me, oh, you can't say this. You can't say that, just due to weather and the time and bring up the next song. So I said, I got to get an outlet where I could just go up on stage. So I went up one night, and the first night I didn't do well, but I knew I got, like, one laugh, and I felt that energy from that laugh, that buzz, and I'm like, man, it was amazing. I'm like, this is. I've never felt something like that before. I'm like, this is what I want to do. And I just dropped everything else and just went for it.
Lynn Ho
Now, that's amazing to me because that was actually one of my questions for you later in this interview was, are comedians like rock stars? But you sort of answer that. Is it the vibe from the audience you get or give. Get back and forth?
Jim Florentine
I don't know if we're really rock stars. I mean, you know, rock stars get all the girls. The comedians don't.
Lynn Ho
True.
Jim Florentine
You know, rock stars, they could be, like, in a cover band down the street, you know, playing this little bar, and they can get girls. The comedian, you know, girls always. I want a guy that laughs, makes me laugh. And then you make them laugh for an hour, and they come up to you and go, hi, you were great. Here's my husband. I'm like that. Thanks.
Lynn Ho
Oh, my gosh. Well, I read that you grew up in a very strict Catholic family. Did that have any influence on your sense of humor and comedic perspective? I suspect yes.
Jim Florentine
Yeah, because I grew up a family of seven Catholic, you know, so just, you know, I just think the whole. The whole ball busting, you know, that's we're just pulling pranks on each other and just, you know, you had to have tough skin hanging out in the neighborhood with all the neighborhood kids, and it was one big, like, big community and stuff. And that's just the way I was raised, is just being, like, a wise ass.
Lynn Ho
Where were you raised?
Jim Florentine
In New Jersey.
Lynn Ho
Oh, and is that where you were in radio as well?
Jim Florentine
Yeah. Yeah.
Lynn Ho
Give him a shout out. Come on.
Jim Florentine
There was. I don't even know if it's around. It was WCNJ in Hazlet, New Jersey. It was a 100 watt station basically. I mean, you know, I, why what I did, I went to this community college, Brookdale Community College, and they had a good communications program. So I was, I was interning on the radio there. I had a little radio show there. I was interning at the station in, in Keyport. And then they went up higher. Me, they let me at night. They would let me play after like 6 o'. Clock. It was an open format. So they let me three hour heavy metal show where I just bring in my albums and play whatever I brought to my friends with me. We do it, they go, look, we can't pay you. I'm like, that's, I don't care. That's fine. Yeah. And then they like my voice and stuff. And then I wound up being the morning guy for about a year at like 21 years old.
Lynn Ho
You wait, you did mornings at 21? So most comedians aren't up early in the morning. So that must have been.
Jim Florentine
It was. I wasn't even doing comedy at that point. Yeah, but yeah, I know it was a 6, 6am to 9am So I had to go to bed at like 8:30 at night. It was torture. But I liked it, you know, and I, I was like, I can't believe I'm the morning guy at this, you know. It was 100 watts. So if you pulled out of the station, went like a half mile down the road, you couldn't get it.
Lynn Ho
Static. No. That's good though. It's. It really. I, I came from a background of radio as well up, up in Boston as a matter of fact bringing. But that back to the DJ stuff. You said you weren't a comedian yet. What made you transition into the world of comedy from radio? And not only that, did you need someone to affirm besides that one person who laughed at you that first night you went up at stand up. I mean that that's a big deal to get up in front of an audience and try to make them laugh.
Jim Florentine
Absolutely. And I was always afraid of public speaking. Even if I had to really do something in high school or college, I had to go out and talk. I was petrified. Maybe I wouldn't even go to school that day. And the DJ can hide behind the mic. And I was also a DJ like in a rock club. And I had my own DJ business where I DJ weddings. So. But you weren't really on the. There was really hardly any public speaking with that. But Then when I was on the radio and they were like, no, you got 30 seconds to get to the next song. Don't even crack a joke. People don't want to hear jokes. And I'm like, I got to be creative somehow. So I started writing stuff down, like topical stuff. And I go, I should go up on stage and do this stuff. And then the radio stuff was just too many restrictions, you know, I went from playing heavy metal at night to, like, it was an ao, AOR station, I guess.
Lynn Ho
Adult oriented rock.
Jim Florentine
Yeah. So it was like I was playing, like, you know, Bill Collins solo stuff. I'm like, I don't want to play.
Lynn Ho
This stuff, especially if you were big and heavy metal. I was also a rock chick in the 80s as well, so I totally. I think we loved all the same bands. In fact, I read that when you were doing this early comedy, you were opening up for heavy metal bands. What was that like? Because you're opening up for Slayer in front of an audience that's there to see a rock show.
Jim Florentine
Yeah, well, that was later on. Yeah. What was when that metal show was on the air, so.
Lynn Ho
Oh, okay, that makes sense.
Jim Florentine
Yeah, it was later on. But no, it was. It was Slayer, Megadeth and Anthrax. Oh, awesome. I was doing arenas. Open them for him.
Lynn Ho
Wow.
Jim Florentine
So I had to do like three five minute sets between each band because Jagermeister hired me. It was like a Jagermeister tour. So I promote Jagermeister and then I do jokes. But I had to do three different sets in front of an arena.
Lynn Ho
Arena.
Jim Florentine
Arena. Yeah. It was. I know. And I was like, man, I go, you know what? I want to do it as a challenge, you know, because I was like, I see if I could pull this off. But it was crazy because at the first set, you know, there's hardly anybody in the venue. So it was great. You know, there's probably a couple thousand. They listen, the second set, they're like, okay, all right. And then by the third set, by the time Slayer's coming on, they don't want any party. You're like, all right, enough, dude. You know. You know when you go to a local show, you go to a concert and the local DJ goes on stage and does all these announcements.
Lynn Ho
Yeah.
Jim Florentine
You know, I was always a drunk guy or the high guy in the audience, go, shut up already. Come on, we're going to miss a song. We don't care. So I know I'm that guy in the audience going, man, they don't want to hear this stuff.
Lynn Ho
No, I totally agree with you. You're always showing up like, okay, who has number 26 under their seat? You won the prize in the raffle before you came in the show, and no one's listening at all.
Jim Florentine
Nobody. And by the time Slayer was on, they were just chanting, Slayer, Slayer, Slayer over my set. And I said, listen, I got to do five minutes here. So Slayer is not coming on for another 10 minutes. I'm not wasting any of their time. I'm not taking away a song by me being up here. So I don't want you to think that. So if you don't like it, go to the bathroom, go get a beer. I got five minutes and do some quick jokes, and we're getting out of here. Too bad. So I tried to do it like that, and it was tough, you know, but I did it for a month. But I just. I wanted to challenge myself with that.
Lynn Ho
That's pretty cool. I mean, that's quite a big challenge. Now, going back to your radio career, prank calls led to appearances on the Howard Stern show, and eventually, that show I mentioned up front, Crank Yankers. That was on Comedy Central, right?
Jim Florentine
Yeah, yeah, it was on Comedy Central. Yeah.
Lynn Ho
Can you share some memorable experiences from that time? Just as a radio brethren here, we used to do something called Nutcrackers with one of my favorite radio hosts of all time, John Lander, up in Boston, years ago, and we got in a lot of trouble. So I can only imagine the stories that you have to tell about phony phone calls.
Jim Florentine
Yeah, well, you know, I originally started doing it where I was messing with telemarketers. They would call my house, and I would just see how long I keep on the phone. Because I was. You know, I didn't have a day job. I was just working at night doing comedy. So I didn't have to go to work till like, 8 o' clock at night. So I'm like, let me just see how long and keep them on. And then I started recording them, and I put. I just made up a CD of them. Like, I produced it myself. I brought it to a local place I made up. I figured I'd get my name out there with some prank calls after a show. I could hand them out or sell them. And then I gave it to the Howard Stern Show. I knew the producer over there, Gary Della Bate goes, all right, man, if it's funny, well, he'll play it. I'm like, yeah, right, whatever. He ain't gonna play it. You know, he's just being nice. And the next Day he started playing all the telemarketer calls. He's like, oh my God, this is amazing. And, and within like a month there's. All of a sudden there's a show called Crank Anchors where they look up for guys to do prank calls. So they hurt Jimmy Kimmel. Adam Corolla was their show. They used to listen to Howard Cern out in la. They heard this good calls. They go, they tracked me down. Like, we've got this guy on the show. So it was crazy. Like, it all happened within like a month.
Lynn Ho
Isn't it amazing how that all comes full circle now that we could never do that again?
Jim Florentine
No.
Lynn Ho
And because you have to let people know that you're about to prank them.
Jim Florentine
Well, it depends on the radio. Yes, you have to, but not in real life. We would. First of all, it's got to be like a one party consent state. So as long as one person know to record in a conversation, you could do it. So we, we went to Nevada, we. And they were already. We do them in California, New York. That's a record. Because we knew they were recording them. But with a prank call and outgoing, you have to get permission afterwards to air the call. So if someone has to call back, hey, would you just prank you? People would get mad. No, I'm not doing that. Like, come on, we'll call you back in a couple days. Let's think about it. And then they would probably, most of the time they would sign off on the release.
Lynn Ho
They were amazing. I had CDs. I listened to them relentlessly. They were just so fun. Did you ever get in trouble? Yeah, I mean, can you give us one experience that you had?
Jim Florentine
All right, so one, it was, you know, the telemarketer stuff. This woman called me trying to sell me a credit card or she wanted to transfer some money into my. I forget what it was, but it was some kind of scam. But she had my address right in front of me. So she's like, maybe, you know, you need some money, you know, maybe something. I go, yeah. I go, I just hit this old lady with my car and I got to pay her medical bills. I just make up stuff.
Lynn Ho
Yeah.
Jim Florentine
And then I'm going through all this stuff, like I just visited the hospital and, you know, this and that. And then finally like, okay, so give me a bank account number so I could transfer the money. So now I have to get out of the car. I'm not giving my. So I just go, I just blurted. So I go, you know, I'm just going to go to the hospital where she's at. I'm going to go smother with a pillow and put her out of misery. And then call me back in like an hour. It's like, oh, my God. I'm going to go, yeah, call me back in an hour. Because I had to get out of not giving away. So next thing I know, a half hour later, I got two detectives at my door because she had my address in front of me. So she thought that something that she believed.
Lynn Ho
Oh, yes.
Jim Florentine
So she called the local police in my town, and they go, you know, you made a prank call. You're pretending you. You're going to go down to hospital again. I go, look, it was just a joke. I. I showed him. I go, look, I have a record off to my phone. I got to work on the show called Crank Anchors. I go, we just make prank calls. And he's just staring at me. I'm gonna go. Give me your id. And I look, he goes at the time, because you're 37 years old. That's what you do all day. Like, they were scolding me. I'm like, yeah, I'm sorry.
Lynn Ho
It was a little juvenile. I love it. That's pretty scary stuff, though, when you think about it. You know, you're just trying to entertain people, and then you realize, oh, I've kind of crossed a line here.
Jim Florentine
Well, I crossed it way more about three weeks later, if you want to hear that story.
Lynn Ho
Oh, yeah, please bring it.
Jim Florentine
So they just said, hey, listen, do the pranks. Just don't threaten anyone. We don't want to come back here to your house. I go, yeah, I promise. And I realized. I go, yeah, I probably went over the line with that. Cut to a few weeks later. I don't know why I came up with that idea where I had my friend over. And when the. When the telemarketer would call, I pretend I've given my girlfriend a home abortion.
Lynn Ho
Oh, no, no.
Jim Florentine
I don't know. You know, you think that I wouldn't think. And then we had a vacuum going on, and she's screaming in the background. I know, it's horrible. I'm going to hell for it. So the woman's like, what's going on? I told. I got my friends, just give my girlfriend a home abortion. I'm just trying to save a few dollars, so just keep going. Don't worry about it. I know they're loud, but it'll be all right. She got. She was on the phone for, like, three minutes. I was Horrified and hung up. Oh, my God. So we started laughing about it. My girlfriend's like, you going to hell? Like, I go, yeah, I know, whatever. So I leave the house. We go get coffee or something like that. I come back like a half hour later. My door is busted in, broken down. The cops came to my house because she had my address too. They thought someone was upstairs in my apartment bleeding. So they kicked the door down, kick the door in to go upstairs and see. So I come back, all my neighbors are out of the outside in the street, but in front of my house, I go, what's going on? They go to. Cops were here, ems, ambulance. I go, for what? I go, I don't know. They came because of some prank call or something. I'm like, oh, man. So I know.
Lynn Ho
Did you get arrested?
Jim Florentine
No. I went. I made the mistake of going down the police station because I wanted to tell him. And it was the same two cops. When I walked in, they go, what is wrong with you? I go, look, man. They go, we just told you. I go, I know. I wasn't thinking. He goes. So they had, like, ambulance, EMS workers, cops, they spread down there because they didn't know.
Lynn Ho
Wow.
Jim Florentine
And I got a ticket for disorderly conduct, and I had to go to court, and I got fined, and the judge yelled at me in front of everybody. It was a packed courtroom. I remember that. He goes, you did a prank call where you pretended you were giving your girlfriend a home abortion. You had a vacuum going on background, and you thought, that's funny, and you work for Comedy Central. Is that what they pass up as funny again? I don't know what I was thinking. I'm biting my lip because I wanted to laugh like a child.
Lynn Ho
I was gonna say, how did you not laugh?
Jim Florentine
Because, you know, in front, and the judge is scolded and the whole courtroom is packed, they just hear people going, o like, what a jerk. What an evil guy like that. I'm like, whatever. He find me. He's like, don't ever do it again. And I had to do, like, the walk of shame through the whole court. Like, walk right through the aisle. Everyone just staring at me like they wanted to stone me to death.
Lynn Ho
You did a perp walk and your girlfriend says, you're going to hell. But she participated.
Jim Florentine
She participated.
Lynn Ho
It's so funny. We never got close to that, but we did do one where someone was dumpster diving for his kids science project, and they had to back up the truck, and he was stuck in there, and he called, I'm gonna get dumped. And then the cops were calling from Florida. Wait, they were looking at all the dumpsters to find where the person was dumped by the sound effects we were playing. Nobody was dumped, so I feel your pain on that too. But super, super fun stuff.
Jim Florentine
We'll be right back with more of the Comedy Save Me Podcast.
Cal Penn
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Jim Florentine
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Lynn Ho
The way we're living.
Jim Florentine
Like our episode where we look at diabetes in the United states. I mean, 50% of Americans are pre diabetic. How preventable is type 2? Extremely. Or our in depth analysis of how incredible mangoes are. Oh, it's hard to explain to rest of the world that like your mangoes are fine because mangoes are incredible, but like, you don't even know.
Lynn Ho
You don't know, you don't know.
Jim Florentine
It's going to be a fun ride. So tune in. Listen to health stuff on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Wilmer Valderrama
What do you get when you mix 1950s Hollywood, a Cuban musician with a dream, and one of the most iconic sitcoms of all time? You get Desi Arnaz, a trailblazer, a businessman, a husband, and maybe most importantly, the first Latino to break primetime wide open. I'm Wilmer Valderrama. And yes, I grew up watching him, probably just like you and millions of others. But for me, I saw myself in his story.
Jim Florentine
From cleaning canary cages to this night here in New York.
Wilmer Valderrama
It's a long ways. On the podcast starring Desi Arnaz and Wilmer Valderrama, I'll take you on a journey to Desi's life. The moments it has overlapped with mine, how he redefined American television and what that meant for all of us watching from the sidelines, waiting for a face like ours on screen. This is the story of how one man's spotlight led the path for so many others and how we carry his legacy today. Listen to Starring Desi Arnaz and Wilmer Valderrama as part of the Micultura Podcast Network, available on the iHeartRadio app, Apple Podcasts or wherever you get your podcasts.
Jim Florentine
The forces shaping the world's economies and financial markets can be hard to spot.
Lynn Ho
Even though they are such a powerful player in finance, you wouldn't really know that you are interacting with them.
Jim Florentine
And even harder to understand, Donald Trump's.
Lynn Ho
Trade War 2.0 is only accelerating the process of de dollarization, which in a way is jargon for people turning away from the dollar.
Jim Florentine
That is where the big take from Bloomberg Podcast comes in to connect the dots.
Lynn Ho
How unusual is a deal like this?
Jim Florentine
Unprecedented. Every weekday afternoon, we dive deep into one big global business story.
Kyle McLaughlin
The biggest story of the reaction of.
Lynn Ho
The oil market to to the conflict.
Jim Florentine
In the Middle east is one of what has not happened. Katie, you told me that ETFs are your favorite thing.
Lynn Ho
They are.
Jim Florentine
Explain that. Why is that the case? And unpack what it means for you. Our breakfast foods are consistent consumer staples, and so they sort of become outsized indicators of inflation. Listen to the big take from Bloomberg News every weekday afternoon on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts. Here we Go.
Cal Penn
Hey, I'm Cal Penn, and on my new podcast, Here We Go Again, we'll take today's trends and headlines and ask, why does history keep repeating itself? You may know me as the second hottest actor from the Harold and Kumar movies, but I'm also an author, a White House staffer, and as of like 15 seconds ago, a podcast host. Along the way, I've made some friends who are experts in science, politics, and pop culture. And each week one of them will be joining me to answer my burning questions, like, are we heading towards another financial crash? Like in 08? Is non monogamy back in style? And how come there's never a gate ready for your flight when it lands, like two minutes early? We've got guests like Pete Buttigieg, Stacey Abrams, Lilly Singh, and Bill Nye.
Jim Florentine
When you start weaponizing outer space, things can potentially go really wrong.
Cal Penn
Look, the world can seem pretty scary right now, because it is. But my goal here is for you to listen and feel a little better about the future. Listen and subscribe to Here We Go Again With Kal Penn on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
Jim Florentine
Welcome back to the Comedy Saved Me podcast.
Lynn Ho
Do you think that comedy serves. Serves as a therapeutic outlet, you know, for both the comedians and the audiences that they're performing to?
Jim Florentine
I think so. A lot of people tell me after a show, thanks. I appreciate it. It was a great show. I needed this. I got some stuff going on in my life. I just need to come out and laugh. You know, people that are, you know, got a. You know, was sick, you know, people had a lot of cancer patients, you know, come out. Like, I just need to get out of the house and laugh for an hour and a half, forget all. Whatever's going on. So I really think it is. And for a comic, for me to make the people laugh too, it's a great adrenaline rush, you know, it really is, you know, and I love that too. Just making people, making people laugh.
Lynn Ho
I was gonna ask you that question right after, but, but, but following it up. When you walk out on a stage, do you feel that comedians are, in a way, empathic empaths because, you know, you sort of vibe off the audience. Can you tell if you've gotta change the audience's mind or if they're going to be receptive right away? Can you feel that in the audience?
Jim Florentine
Yeah. Well, one good thing about comedy is you can't mail it in because every set is different. Every night is different. You could do. I could do a show at 8 o', clock and they're amazing. I could have filmed it for a Netflix special. And then the next show, an hour and a half later, they're staring at me with the same exact jokes. So you always. So I love that about it, where I just can't go, okay, I'm just gonna go up there. I can. This is easy. It's never easy, and I love that because sometimes you have to figure it out. All of a sudden it's not working. So you have to feel, okay, this crowd's really not going for this kind of material, so let me switch it up. You're always thinking up there, which I like. You're almost like a quarterback at the line before the play calls. You're looking, okay, maybe I have to change the play here and stuff. So I love that about it. Sometimes you just don't connect with the audience. They're just not buying it. They're not into it, and there's nothing you could do. You could try, but so, you know, so you have those sites I just chalk it up as a bad day at work. Everyone has a bad day at work. So for me, that was a bad day at work.
Lynn Ho
Well, speaking of that, when you have a bad day, who makes you laugh?
Jim Florentine
Yeah, I think if I'm having a down day, I don't necessarily have to put on comedy. Maybe I'll just watch something that's dumb, like a Netflix here, just to zone out. Mindless, Mindless. Or I'll watch sports. Just mindless, because sports is really mindless, especially if you're not really cheering for the other team. Or, like, watch SportsCenter, like sports highlights or something like that. Just something really dumb. I always had a. For years, I had to go to bed. I had to have the TV on. I just. For some reason, I couldn't sleep without it. And I'd always put, like, Sports center on because it's just dumb sports highlights where I don't get into. I can't watch a movie. I'm like, oh, my God, what's gonna happen next? I still have that adrenaline stuff. So I just did the dumbest the better. So if I'm going through a bad day, not necessarily comedy, but I'll put on some kind of series and watch.
Lynn Ho
That's cool. Well, what would you say would be the defining moments for your career, both both positive and negative? And how have they shaped you today as a comedian?
Jim Florentine
Well, just Howard Stern discovered me through those prank calls and then having me on the show. You know, this is like 2001 jacketed joke, man. Martling, he was one of the sidekicks on the show. He left the show, and they had an open chair now, and they're all. He started having all these young and unknown comics come in and sit in on the show. And it was just perfect timing with all of that. And I was one of those guys that would sit in, and he would have me on the show as a regular. This is when he was on regular radio. He had 20 million people listening. You know, I was doing all the clubs. No one really knew who I was. And then all of a sudden he say, jim's going to be in Pittsburgh at the Improv this weekend. I would sell out five shows automatically just from him with that one plug, just like that. So that took my career off. Then I got the crank anchors from being on Stern and everything else helped through that show because it was so big and massive at that time.
Lynn Ho
Are you addicted to making people laugh or the good that it creates? Would you say?
Jim Florentine
I don't. You know, it's Weird with comics, you know, usually the guy that tries to be the life of the party, he's a terrible comedian. The guy who sits back and kind of sarcastic and quiet, doesn't need to, you know, have the whole room, you know, with the attention, put the lampshade on his head. That guy, that guy's not going to be funny. But the other. But the other comics just sit back and observe and watch. That's how they come up with their stuff. So I don't need to be funny all the time. Sometimes I do, you know, like I coach my kids rec basketball team and you know, all the guys, he's like, dad, don't crack any inappropriate jokes. I go, no, I'm not. And when I have his parent teacher meeting, I go, I'm not going to do that. I know when I have to. And one of the moms goes, I never knew you were a comedian because you're never really that funny. I go, yeah, because I'm hanging out, we're watching our kids, you know, play basketball. We're talking about this, the referee and that shot or whatever. I go, I don't need to command the whole room here. When I'm on stage, that's the only time I need to.
Lynn Ho
Do you think laughter is the best medicine?
Jim Florentine
Yeah. I mean, it is for a lot of people. Yeah. Really? You know, it gets people in a better mood, you know. Absolutely. It definitely does. And there's nothing like a live comedy show because you never know what happens at a live show. You can watch it on tv. It's not the same effect. It's almost like watching a concert on tv.
Lynn Ho
Yes.
Jim Florentine
When you're there, it's special. And when you're in a people come to show go, this is my first comedy show. I used to watch on tv. It was amazing just being in the room because the tension with. And you saying that it's picking on the crowd and working the crowd and this guy and that. I go, yeah, because you never know on a live show what's going to happen.
Lynn Ho
Why do you think comedians are? I've interviewed quite a few in my lifetime and I've noticed the one thing that always surprises me is how down to earth all comedians are. Do you think it's the line of work or do you think it's how hard you work versus, you know, actors, musicians? It seems like comedians are the hardest working people in show business.
Jim Florentine
Yeah. And I, you know, I guess maybe if you get to a certain point, your ego gets in the way. But we just know, like we're just, every day we think that this, at some point we're not gonna have a career anymore. Something's gonna happen. So we always had that fear. I do, you know, and I think a lot of comics do so. And we're not flashy, you know, actors. That's a whole other thing with the ego and the narcissism and stuff like that. I mean, I guess some of the comics, but, but general, we're just happy that we're making a living. We're making people laugh and we're our own boss, which is huge. We can dress the way we want, say whatever we want, and we don't have a boss to listen to.
Lynn Ho
It's pretty awesome. This is one of those questions that I just always love to hear the answer to. If you had your choice, living or dead, who would you love to headline with and what would that show be or look like if you could perform with anyone?
Jim Florentine
Rodney Dangerfield, he never gets like, like his catchphrase. You never gets respect. Like, a lot of people don't say he was an influence on him. Like, when they talk about comedy, comedians always go, Richard Pryor, George Carlin, Eddie Murphy, they never put Rodney in there. To me, Rodney was a huge influence.
Lynn Ho
He's amazing.
Jim Florentine
You know, I just love to set up punts, set up quick, quick one liners. I love that. Just self deprecating. And I would have, you know, I met him a couple times. Obviously I never did a show with them, but I would have loved to do, to do shows with Rodney.
Lynn Ho
I would have loved to have seen that.
Jim Florentine
And just watch him and watch him every night. Like if I was on tour with them and just watch him every night, it would be amazing.
Lynn Ho
Do you, do you find that people come up to you and say, hey, Jim, meet my friend so and so, go ahead, be funny, say something funny.
Jim Florentine
Yeah.
Lynn Ho
How does that work?
Jim Florentine
I just, I'm like, look, man, I'm not at work.
Lynn Ho
And then they laugh because you're sarcastic when you're funny too, right?
Jim Florentine
I just go, yeah. I go, you know? Yeah. It's not. I hate when people do this. When I have like family members or people that know me, hey, you know, introducing me to strange people. Hey. And he's a comedian. I'm like, you don't have to say that. I go, please. I go, I didn't say, hey, he's. He does construction. When I introduced you. Yeah, hey, he's a lawyer, you know, so why did you. Don't. I go, leave that out.
Lynn Ho
That's A good way to do it. That's, that's pretty cool. That's creative, right?
Jim Florentine
Because what then what happens is. Oh, really? Comedian. Oh, you know, so, you know, you write your own jokes. Where do you perform? You just said it's a million dumb questions. And it's like, I'm not at work. Right. I don't want to answer these when I'm at a party. Where do you get your material from? I go, I get it from you because you bother me and you'll be in my act.
Lynn Ho
Tune in tomorrow.
Jim Florentine
Well, I could see. I could. I'm sure, like a doctor goes to a party, I'm sure he's like, hey, doc. Oh, you're a doctor. I got a lump right here. Is this anything to worry about?
Kyle McLaughlin
Yeah.
Lynn Ho
Does this look infected?
Jim Florentine
Right. Or a dentist, Is this the root canal? You think I'm missing a cap here? You know, so I guess they get that too. But it's so true. I always tell people, if I'm in a plane, they go, what do you do for a living? Because you tell me you're comic, you're talking to that person for two hours. Right?
Lynn Ho
Right.
Jim Florentine
So I just go, yeah, I, I do landscaping. So there's no. They're not going to ask anything about landscaping. Yeah, I cut lawns, I mow lawns, I do landscape. And no one's going to go, really? What kind of mower do you have?
Lynn Ho
That's great. I never even thought of that. When anyone asked me, I would always say, I sell shoes.
Jim Florentine
That's a good one too.
Lynn Ho
Because no one cares about that either.
Jim Florentine
No one's going to be like, really? What kind of shoes? I just work at a store. Whatever the shoes they want, but the landscape. And nobody's ever going to, I don't even say own the business. Oh. Because then they go, you own the business. How does that work? I go, no, I just work for a guy.
Lynn Ho
Yeah. Yeah. Even better. Yeah. What is my last question for you? What? I mean, you've done it really all movies, television, voiceovers, you're a comedian. What does it feel like when you really connect with an audience or even just a one on one? When you've really made somebody's day and you can really tell that they've, they're having a great day because of your comedy. How does that feel to you?
Jim Florentine
It's amazing. It's the best feeling in the world. It's like I. It's equivalent to having an orgasm.
Lynn Ho
Really.
Jim Florentine
Yeah. That you can connect with a crowd and they like You. And then also, like new jokes work, like if you have new material, you just can't wait to get on stage and do. And if it works, it's, it's an unbelievable feeling. And any comic will tell you the same thing, like, oh my God, I can't believe. Because you could come up with 10 ideas, 10 jokes and maybe four you are going to work. Six are just not going to work. You have to try them in front of that crowd. But once they do work, it's unbelievable. It's the best feeling in the world.
Lynn Ho
I, I told you that was the last question, but I had one more. Is that okay?
Jim Florentine
That's all right.
Lynn Ho
All right.
Jim Florentine
Yeah, sure.
Lynn Ho
Upcoming projects and themes that inspire you right now. Personally, how do you see yourself moving forward from here?
Jim Florentine
You know, I don't. You know, I think as a comic you could just keep working until, you know, there's no set age. So I'm just going to keep doing it until I feel like I don't want to do it anymore. But there's, you know, you don't have to retire at certain age or any of that stuff. So I still love doing it. Who knows at some point. But you know, my son's now, he's 14, so he'll come to a lot of my shows. He's getting into comedy, just not on stage, but watching. He loves all the comics and stuff. He loves being at the shows and all that. So it's good that he could see that.
Lynn Ho
That must make you feel so proud.
Jim Florentine
It's great. Yeah, that he could. He's like, oh, man, next time you go to Austin, I want to go to Joe Rogan's club with you. I go, yeah, no problem. You know, stuff like that. So it's great that I could show him that, you know, so. But yeah, just, you know, continue doing a stand up. That's one thing. It doesn't matter how old you get, what you look like, you can always still be funny. You can make fun of the way you look, how old you are, whatever it is, and as long as you can connect with an audience, you could do it forever.
Lynn Ho
And is laughing at yourself pretty much the price of admission. You have to be able to laugh at yourself.
Jim Florentine
Absolutely. Yeah. Like if someone comes back with something funny in the crowd, like if you're picking on him and the guy says something back to you go, yeah, that's a good one. You got me. You know, I get it, you know, so, yeah, you got to laugh for yourself too. A lot of comedians are sensitive too you know, they don't like to get critiqued, but that's just the way it is. You don't, you know, I don't worry about that. Like, people don't like my stuff. I understand it. You're not going to appeal everybody. As soon as you try to appeal to everyone, you're just, you're never going to make it. You're just going to be middle of the road trying to make everybody happy. Just everyone's not going to get your comedy, no matter what kind of comedy you do. And don't take a personally if four to 10 people don't get it. Just focus on the six that do. That's the way I always looked at it.
Lynn Ho
Great advice, really. And great advice for anyone doing anything in general, really. Not just comedy. Right.
Jim Florentine
And even bands, you know, if, you know, of course some people aren't going to like that music, so they're not going to get it. Like people always ask me, you know, what do you think about these new bands, you know, or even like a Taylor Swift? I go, I'm not supposed to like that. So I can't. You know what I mean? That's not even on my radar. I'm not a teenage girl, so I'm not gonna, you know, or even like Kendrick Lamar at the super bowl halftime show. I go, I'm not supposed to like that. So my kid understands that and likes that side of stuff. So I can't trash it because it's not for me.
Lynn Ho
That makes sense. That makes sense. Well, it's been such a pleasure getting to catch up with you and talk with you. And where can people find your latest travel so that they can catch you? Besides television, where are you going to be performing? Do you have a website?
Jim Florentine
Yeah, I got a website. Jimflorentine.com all my tour dates are on there. My latest comedy special is you can't please them All. It's on Amazon Prime. You can see it up there.
Lynn Ho
Jim Florentine, thank you for giving us all your healing gift of comedy. It was again, great chatting with you and I hope that I get to see you again soon. And I'm sure I'm going to see you on TV very soon.
Jim Florentine
I appreciate that. Yeah.
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Kyle McLaughlin
Hey, I'm Kyle McLaughlin. You might know me as that guy from Twin Peaks, Sex and the City or just the Internet Stand. I have a new podcast called what Are We Even Doing? Where I embark on a noble quest to understand the brilliant chaos of youth culture. Each week I invite someone fascinating to join me to talk about navigating this high speed rollercoaster we call reality. Join me and my delightful guests every Thursday and let's get weird together in a good way. Listen to what Are We Even doing on the iHeartRadio adventure, Apple Podcasts or wherever you get your podcasts.
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Welcome to Decoding Women's Health. I'm Dr. Elizabeth Poynter, Chair of Women's Health and Gynecology at the Atria Health Institute in New York City. I'll be talking to top researchers and clinicians and bringing vital information about midlife women's health directly to you. 100 of women go through menopause. Even if it's natural, why should we suffer through it? Listen to Decoding Women's Health with Dr. Elizabeth Poyner on the iHeartRadio app, Apple Podcast, or wherever you get your podcasts. This is an iHeart podcast.
Release Date: November 7, 2025
Host: Lynn Ho (Comedy Saved Me replay episode, as part of the Takin’ a Walk series)
Guest: Jim Florentine
This episode is a lively and candid conversation with veteran comedian Jim Florentine. Best known for his outrageous prank calls on the Howard Stern Show, his work on Comedy Central’s "Crank Yankers," and appearances in the heavy metal scene, Jim shares how comedy became not just a career but a lifeline. The show explores Jim’s roots, the evolution of his comedic style, the challenges (and misadventures) of prank call fame, the therapeutic power of laughter, and why comedians remain grounded even as they bring joy to others.
Timestamps: 02:47–06:35
“All of a sudden, comedians started being like kind of like rock stars… When I saw Andrew Dice Clay, Sam Kinison, I thought that's what I want to do.” (Jim Florentine, 04:35)
Timestamps: 06:53–09:56
“They let me… do a three-hour heavy metal show… I brought my albums, my friends, but eventually got stuck playing Phil Collins.” (Jim Florentine, 07:00)
Timestamps: 09:32–11:43
“I had to do three five-minute sets between each band… By the time Slayer was coming on, they were just chanting ‘Slayer’ over my set.” (Jim Florentine, 11:13)
Timestamps: 11:56–18:36
“Within like a month… all of a sudden there’s a show called Crank Yankers… Jimmy Kimmel and Adam Carolla… tracked me down.” (Jim Florentine, 13:22)
“She had my address… next thing I know, two detectives at my door… you’re 37 years old; that’s what you do all day?” (Jim Florentine, 15:24)
“You did a prank call... pretending you were giving your girlfriend a home abortion… and you thought that’s funny?” (Judge recounting, 17:49)
Timestamps: 24:15–27:13
“A lot of people tell me after a show… ‘I just needed this.’ I got some stuff going on in my life, just needed to laugh.” (Jim Florentine, 24:23)
“You can’t mail it in… every night is different… I love that about it.” (Jim Florentine, 25:20)
Timestamps: 27:13–29:41
“It’s the best feeling in the world. It’s equivalent to having an orgasm… when the new stuff works, it’s unbelievable.” (Jim Florentine, 34:31)
“We just know… at some point we’re not gonna have a career anymore. So we always have that fear… We’re just happy that we’re making a living, making people laugh, and we’re our own boss.” (Jim Florentine, 30:21)
Timestamps: 31:00–33:41
“I hate when people… introduce me to strangers and say, ‘he’s a comedian.’ I go, you don’t have to say that… Please!” (Jim Florentine, 32:16) “If I’m on a plane, I just say ‘I do landscaping’… no one’s going to ask anything about landscaping.” (Jim Florentine, 33:28)
Timestamps: 36:19–37:42
“As soon as you try to appeal to everyone, you’re never going to make it... just focus on the six out of ten that do get you.” (Jim Florentine, 36:19)
“People always ask me… about Taylor Swift… I’m not supposed to like that. That’s not even on my radar.” (Jim Florentine, 37:14)
Timestamps: 35:13–38:05
“I just got to get an outlet where I could just go up on stage… I got one laugh and I felt that energy from that laugh, that buzz… this is what I want to do.” (Jim, 04:35)
“She had my address… so next thing I know a half hour later, I got two detectives at my door…” (Jim, 15:24) “Is that what they pass as funny at Comedy Central?” (Courtroom judge quoting Jim’s prank, 17:49)
"Every day we think that this, at some point we're not gonna have a career anymore." (Jim, 30:21)
“It’s equivalent to having an orgasm.” (Jim, 34:31)
“As soon as you try to appeal to everyone, you’re never going to make it… just focus on the six that do get your comedy.” (Jim, 36:19)
“I just go, yeah. You know, it’s not—I hate when people do this, when I have like family members… ‘Hey, and he’s a comedian!’ I go, you don’t have to say that!” (Jim, 32:16)
“My son…loves all the comics… it’s good that he could see that.” (Jim, 35:52)
The episode delivers a rich, insightful, and at times laugh-out-loud account of Jim Florentine’s chaotic, heartfelt, and hilarious career. With advice to aspiring comics and everyday people alike, Jim makes clear that comedy is as much about resilience and authenticity as it is about punchlines—and that it has the power to heal on both sides of the microphone.
For tour dates, specials, and more:
JimFlorentine.com
Latest special: You Can’t Please Them All (Amazon Prime)