Jim Florentine has been a successful road comic for more than two decades, but in his early years, he did his fair share of bizarro gigs. Getting his start, backyards, basements and bachelor parties were the norm. He even had the occasional gig sans sound system. “I did one in a restaurant where it supposed to be this private party in one of the rooms,” Florentine said. “But they didn’t have a sound system. So I was standing in the middle of a restaurant telling jokes as waiters and waitresses and people at tables were going, ‘What the hell is this guy doing with no microphone?’ But there’s a point early in your career where you just take any gig you can.”
That is unless it involves dressing up a superhero. “I was struggling for money, and this guy had a business where if they needed a comedian for a bachelor party, they would book me,” Florentine said. “He said, ‘Listen. I got an offer for you. Do you want to do a kids party? You have to dress up as a ninja turtle. You’ll make $125 bucks for 2 hours. Just walk around the party in the costume and take pictures with kids.’ ”
Stand-up sets with no microphone is one thing, but donning a kids costume was a bridge too far. “I was like, ‘I can’t do it,’ ” Florentine said. “And I needed the money bad. He said, ‘No one is gonna see you.’ I still turned it down. I said, ‘If I’m dressing up like a ninja turtle, my career is over. I’m not a comic. Thank God I turned that down.”
For Florentine, those lean years have long been a thing of the past, and the New Jersey native has stayed busy recently with steady road work. The veteran stand-up has also just released his new special, “Bite The Bullet,” for free, on YouTube. Florentine is a former regular on The Howard Stern Show and a former co-host of the cult VH1 Classic series, “That Metal Show.” Currently he’s a cast member of the puppet prank phone call show “Crank Yankers” on Comedy Central, and Florentine’s podcast, “Everybody is Awful (Except You),” was picked up by the Barstool Sports franchise in 2020. Recently, Florentine talked about returning to road work, opening for Bill Burr, his podcast, roasts and comedy career.
Q. Do you still learn things at this stage in your career from watching other comedians like Bill Burr? Definitely. I love how Bill just takes chances. He does over an hour of material, and he’s working it out on stage, and he never knows where it’s gonna go. He’s always pushing the envelope on his bits. I was always fascinated with guys like that.
Q. Have you notice an uptick in interest in the podcast since it being picked up by Barstool Sports? Yeah. They have a younger audience, and they basically said, “Do exactly what you were doing. We’re not gonna censor anything you say.” They’re awesome. Dave (Portnoy, Barstool Sports owner) was a fan of ‘That Metal Show.’ He isn’t a big metal head, but he was fascinated by seeing just these three dudes talking about music. I met with him, and he said “Bring your podcast over here, and we’ll do some version of ‘That Metal Show’ in the future.” Then the coronavirus hit, so everything is on hold for now. I’ve always followed Barstool Sports even before this, and they’re always pushing buttons and causing problems, and I like that.
Q. How did you come up with the character “Bobby Fletcher” for “Crank Yankers?” That was just me, and they just said, “Don’t use your real name.” I have a friend, Artie Fletcher, whose real name is Robert, he’s a comic. So that’s where the name came from. They said, “Just be yourself. Rude and obnoxious.” So it’s basically just me with a different name.”
Q. Will “Special Ed” be making a return? We’re working on it. It’s 13 years later, and times have changed. It’s not me saying “No,” we’ll put that way. But it’s not out of the question. We got picked up for another season, so I’m hoping.
Q. You’ve done a variety of gigs throughout your career, including a one-man show and opening for Slayer. Does doing shows like that sort of prepare you for anything? I like performing in front of different audiences. It’s a challenge. It’s always great to work out material in front of crowds that don’t know you, because you really know if your material works. If you’re just constantly performing in front of your own crowd all the time, they’ll laugh just because it’s you. So I like doing different shows — opening for Bill, doing shows with bands, it’s all a different set of challenges.
Q. As a notorious ball-buster, what are some of the most memorable pranks you’ve pulled on your comic friends? Me and Jim Norton would go to the back of the room at like The Comedy Cellar or Caroline’s, and Rich Vos would be on stage. And whatever joke he said, we would groan at it. And what happens is it gets the rest of the crowd groaning. It’s almost contagious. Then after every joke, he’s getting frustrated and saying, “You guys groaned at that!?” Meanwhile he has no idea we’re in the back of the room. We’re just ruining his set! Norton also had this joke about playing little league, and it had a really dirty punchline. It was disgusting. He would be on stage at The Comedy Cellar, and I’d yell out, “Hey Jim do that little league joke! You guys gotta hear this. It’s one of my favorite jokes. Come on, Jim! Do it.” And the whole crowd would join in, “Come on, do it!” And he would tell his joke, and in it his father molested him at the end. And the crowd would groan and no one would laugh at it! (laughs) We would do stuff like that all the time just to amuse ourselves.
Q. A few years back, you were a part of the Rich Vos roast, which is one of the funniest ever. We’re all friends and we know each other. I think that’s what a roast should be, instead of having Martha Stewart roast random celebrities. Get a bunch of friends that know each other. Those are the best roasts. Those Dean Martin roasts, all those guys knew each other, and they would just bust balls. It was a fun time doing that. I loved it.
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