The Incredible Light and Dark of Jim Florentine
Catch Jim Florentine performing comedy in a live streaming event this Saturday night with Don Jamieson. They’re performing live from Jonathan’s in Ogonquit Maine and streaming everywhere. Go to watchlivenow.com for tickets and more information.
I’ve been a fan of Jim Florentine since I first heard him on the Howard Stern Show. His phony phone calls, funny stories and ability to shoot zingers at anyone who had’em coming made him feel like a natural part of that all-star team. Then, once Fred Norris started in with a spot-on impression of Florentine’s signature deep voice, Jim became a legend in my book. After spending some time talking with him I was impressed by his humility, resilience and charm and I learned that from our Catholic upbringings and close encounters with suicide, to our love for our mothers, Howard Stern and Andrew Dice Clay, Jim Florentine and I actually have a lot in common.
Jim Florentine grew up in a big, Catholic family with 7 kids, a hard working dad and a sweet mom that he described as being, “the Mother Teresa of New Jersey” for her ability to take anyone in who needed a place to stay. Jim gave his strict Catholic upbringing credit for leading him into the arms of comedy when he was a kid. He said, “Growing up Catholic I was always getting into trouble. I was wild and I was always grounded and stuck inside so I would make prank calls because I was bored. I would just pick up the phone and hone my craft… Little did I know how much it was going to help me out later in my life. When I was older and already doing stand-up, I’d get bored when I was home alone during the day so I’d wait for telemarketers to call the house and I’d try to keep them on the phone as long as possible because I didn’t have a show until 10:00. I’d literally keep some of these people on the phone for an hour just to see how long I could string them along. Then I started taping my calls and eventually I put a CD together to sell after my shows to get my name out there. I actually ended up getting the Crank Yankers gig from that CD.” I was also raised in a Catholic family and I told Jim that although my mom never gave up on her faith, she resented being raised in such a strict environment and decided to be the complete opposite when she became a mom. So, even though we went to CCD on Saturdays and church on Sundays, we were still the “cool house” that everyone knew to come by after school for fun hangs. One of my favorite things we’d do was use our karaoke machine to record ourselves making prank phone calls so naturally, I love Crank Yankers. I was curious how his CD ended up landing him that job and that’s when Jim explained just how significant Howard Stern was in breaking his career in comedy.
It turns out that Jim and his buddy Don Jamieson went up to Stern’s executive producer, Gary Dell’Abate’s office and gave him that CD. Gary was like, “If it’s good, we’ll play it on the air” but he had a stack of about 100 CDs on his desk so Jim never thought he’d actually play it but the very next morning, they started playing it and as if that wasn’t wild enough, Howard actually loved it! He said, “Oh my god! Who is this? He’s really funny! We’ve got to get this guy on the show!” and that’s how Jim started getting booked as a guest. About six months after that, Jimmy Kimmel and Adam Carolla, who were already doing The Man Show on Comedy Central, became producers on a new show called Crank Yankers and when they heard Jim Florentine’s prank calls on Howard Stern they instantly loved him and wanted him on their show. The timing of these events are completely insane! Never in the history of TV was there ever a prank phone call TV show and Florentine was the only unknown guy who got cast to be on it.
The original cast of Crank Yankers was Dave Chappelle, Jimmy Kimmel, Adam Carolla, Tracy Morgan, Sarah Silverman, Dane Cook and Jim Florentine. He was the only one that no one had ever heard of and yet when his manager called and told him they wanted him for the show he said, “That sounds like a terrible idea! No one’s going to watch that!” Jim even recalled being worried that his comedian friends were going to make fun of him for being on “the worst show in history.” He said that even after starting the job he still had no idea what the show was going to look like because he’d just go into the recording studio and make calls for them and they would put it all together in post but then it finally aired and completely took off! What an amazing story! What are the odds that all of those stars would align with such perfect timing? Crank Yankers was definitely meant for Jim but even if he never got Crank Yankers, I didn’t want to gloss over the fact that simply being on The Howard Stern Show at all is an extremely ginormous deal! I grew up on Howard. My mom was actually the one who introduced me to the show. She loved him and always had him on the radio so I needed Jim to tell me everything about what it was like being on The Howard Stern Show.
He said, “I was a huge fan of his growing up. I worked landscaping and construction in New Jersey and I’d be on these construction sites telling everyone that they couldn’t put on power saws or lawn mowers or make any noise until he went to commercial because I didn’t want to miss the show. That was the rule. Then all of sudden, I was going to be a guest on the show! If it wasn’t for Howard putting me on, I don’t know where I would be. I’ll always remember that. I was doing comedy at that time and nothing was really happening and getting on Howard Stern was like doing The Tonight Show with Johnny Carson. All of a sudden, I’m selling out Improvs. You know, he plugs it and I’m selling out 5 shows. It was insane! He’d have me on three or four times a year, for like 7 or 8 years, which was perfect. It was great! He basically took misfit comics in and put us on the air which gave us exposure. Howard was a great launching pad. He’d have you on for a few years and then he would move on and bring other comics in. I always knew that, so I never took him for granted and I never got mad. There were some people who got bitter if they didn’t get put on, but I didn’t. I just wanted to do as much as I could while I was on the show and then be ready to move on.”
Everyone who listens to Howard Stern knows Robin Quivers and knows that she is a beautiful, funny, smart, single woman but what you might not know is that our buddy, Jim Florentine, actually took her off the market for a while. That was a big deal because she’s only ever really talked about relationships with two men on the air and that was with “Mr. X” and Jim Florentine. Being a life-long fan, Jim would know this so I wondered how he got the guts to ask her out? He said, “I was on the show one time and it came up that I was single. Howard was actually the one who brought it up. He goes, ‘Hey, Robin you know Jim’s single? You’re single. Why don’t you guys go out?’ We were all laughing and between me, Artie Lange, Howard and Robin we all started making jokes and busting balls. Then finally after about 45 minutes she goes, ‘You know what? I’ll go out with you.’ And I was like, ‘Whoa! What?!’ I couldn’t believe it! It really was unexpected. I mean, I didn’t ask her out in the hallway or after the show. I wasn’t planning on asking her out, it just came up on the air and she was like, ‘I’ll go on a date with you. Why not?!’ and I was like, ‘Wow! Ok!’ Unfortunately, it didn’t last too long. Having completely different schedules was really tough and that put a strain on the relationship but it was fun and she was great. It was a great relationship; it just didn’t work out. I always tell comics, ‘Look, you’re going to ruin a lot of relationships by being in this business because we don’t work on a regular schedule like everyone else. There’s going to be someone you could’ve married or had a real relationship with but it will either be that or your career because it’s tough to juggle both.’ A lot of people can’t put up with the lifestyle of us working every Friday and Saturday and going out 4 or 5 nights a week.”
Truth be told, Robin Quivers never had anything bad to say about Jim, even after they broke up. She was always very positive about their relationship and that was very interesting advice he was offering to young comics. It sounds like comedians really have to make a lot of sacrifices for the love of comedy. Jim said, “You do and there is no promise that you’re going to make it either. It’s not like going to medical school or something like that where you know at the end of it you’re going to have a job. You don’t know. You have no clue. But after a few years in when I was finally making about $350 a week and to me, I had already made it. I was living at home, didn’t have any bills and I was making a living off of what I loved. I was barely getting by but I didn’t care because I wasn’t doing it for the money. To me, that was just a part of being a comic and never once did I think, ‘This sucks.’ It was just what I had to do.” That reminded me of what Bill Burr did when he first started comedy. He knew he was going to be poor in the beginning so he just lived at home and saved his money. There’s something about comedy that’s completely compelling. It has to be a calling because to Jim’s point, there is no guarantee you’re going to make it and I’ve heard so many stories of the poverty and even homelessness comedians have to go through in the beginning because they just aren’t making money at the open mics. There is no person that would be able to make it through those hurdles unless they truly love telling jokes.
Jim Florentine gave Howard Stern credit for breaking his career as a professional comedian and T.V. star but he gave another one of my favorite comedian’s credit for igniting his love of telling jokes and inspiring him to become a stand-up comedian in the first place and that person was Andrew Dice Clay. Jim said, “When I first saw Dice on that Dangerfield’s special I was cutting laws for a living and I was like, ‘Man, that is what I want to do!’ but it still took me about two years after that to get up on stage because I was always afraid of public speaking. I was petrified of it and Dice was a huge influence on getting me up there on stage for the first time.” Jim’s first time on stage was when he was on vacation with a girlfriend in Florida. As fate would have it, while driving from the airport to the hotel, he happened to spot a sign that said “Open Mic Comedy, Tuesday Night: Call to Sign Up”. He felt like that would be his perfect opportunity because nobody would know him down there so he called and signed up. He laughed and said that signing up to do that mic, ruined the vacation because he was so nervous, he’d just walk up and down the beach, rehearsing his lines and his girlfriend got pretty annoyed that he was too busy putting together his set to hang out with her… His personal sacrifices had already begun and he hadn’t even set a foot on stage yet. I wondered if all of that preparation paid off for him at the show and Jim said, “No. I was terrible… but I got one laugh. The jokes weren’t working at all but some guy said something in the audience and I said something right back and when I felt that laugh and the adrenalin rush, I loved that feeling. It was like, ‘Wow, this is what I want to do!’ It’s funny because the guy who was hosting the show that night was from New Jersey, right next to my home town and was just in Florida visiting his grandmother. He let me know that he hosted an open mic every Tuesday and invited me to come down. I ended up doing his open mic every Tuesday after that.” I couldn’t believe it! It was another story of the stars perfectly aligning for Jim! The universe talks back and it was clearly saying that Jim Florentine was meant to be a comedian!
The beautiful alignments didn’t stop there for Jim Florentine either. It was Andrew Dice Clay who inspired him to become a stand-up comedian and Jim got to meet his inspiration on his very first day he was ever in L.A… and he didn’t just meet Dice, they became instant friends! Jim said that he and Jim Norton were in L.A. to shoot a showcase show that Louie Anderson was hosting at the time. Jim and Jim were roommates and both huge fans of Andrew Dice Clay’s. He said they listened to his albums so much, they actually knew all of his jokes by heart. He recalled being in L.A. for the very first time and being at rehearsal for Louie Anderson’s show when Rich Vos called and let them know that Dice was at the Comedy Store (now that’s a good friend)! Jim and Jim dashed out of there and took a cab to get to The Store as fast as they could. When they got there he said, “We walked in and saw Dice hanging out in the back so me and Jim went up and told him we were fans and how much we loved his album, The Day the Laughter Died, where he bombs. We started quoting some of his jokes to him and he didn’t even remember some of the jokes we were telling him but he liked the fact that we knew them so he goes, ‘Hey, why don’t you guys go up on stage tonight and do those jokes for me and my friends?’ He told the manager to put us up and we went up there on two different mics and did Dice’s jokes. The crowd had no idea they were Dice’s so they were just staring at us because they were really dirty and disgusting and made no sense coming from us but we loved them. Dice and his friends were in the back booth absolutely dying the whole time! Then we went in his car afterward because I recorded our set and we listened to it in his car and he was like, ‘Man, I like you guys. You want to go shopping tomorrow?’ Of course we said yes but Jim and I were both thinking he’d never call. Then the next day at noon he came and picked us up at our hotel and we spent the day shopping with him. After that, eventually we started opening for him.” These are the kinds of stories I live for! They literally sound like a dream you would have as a kid… but these are not dreams, these are Jim Florentine’s actual life!
Not everything in Jim Florentine’s life has had such a fairy tale ending, so please do not get it twisted. This man may have had some high, highs, but he has also known suffering and been closely acquainted with tragedy and I feel honored that he was kind enough to talk about some of those experiences with me as well. We discussed our mutual experiences of both losing and finding a loved one who had taken their own lives and talked about the ways we coped with the trauma and loss of it all. For me, it was my aunt who lived with my family since I was in 2nd grade. I was 14 when it happened and although I saw a counselor, I wasn’t really ready to acknowledge what I was actually feeling at the time. Ultimately, I give that experience credit for inspiring me to become a school counselor and being able to help kids when they need it is extremely cathartic for me in a lot of ways.
For Jim it was his girlfriend of 6 years, whom he lived with and he shared his story of how he made it through that difficult time. “When something like that happens, they say it’s even more traumatic if you find the person, so that just adds another layer. I knew I had to deal with this thing head on so I went online and found a survivors of suicide support group and about a week after it happened I went to my first meeting. It was like an AA meeting. You walk in and you see these people who lost their love one maybe 3-4 years ago and they’re in a better place because it gets better as time goes on. But, when I first walked in and they were all laughing, I was like, ‘How could they be laughing when they’ve lost somebody?’ You don’t get it because you’re in the first week and it takes a long time before you start to slowly move on from it. I just sat there and it was really rough but I went back every week even though I hated it. It was so heavy. Everyone told their story and I had to tell my story but it really helped. I went every week for the first 6 months and that definitely helped me get through it but it was rough. I don’t wish that on anybody. A death like that is not like a car accident or cancer or a heart attack. Suicide is a whole other thing. There is so much blame and guilt and then you get mad… and then you feel bad for being mad at them. It’s a whole rollercoaster of emotions you have to go through. I was lucky to know that I couldn’t numb it with booze, sex or whatever. I dealt with it head on so that it wouldn’t affect me my entire life. I was lucky that I was older. If I was in my 20’s or teens, forget it. I would’ve dealt with it 10-15 years down the road.”
In addition to the support group, Jim also sought the guidance of a shaman to help him gain insight and heal during this traumatic stage in his life. Being a half Brazilian woman, shamans and Amazonian healing is in my blood. I would love to see a shaman and was very interested to learn what the experience was like for Jim and what he took away from it. He said, “It was about a month afterwards and I was a mess. I had a friend who recommended I go see him. They kept saying that he could really help me and finally she was like, ‘What do you have to lose?’ I really didn’t have anything to lose so I flew to California to go see him. I remember knocking on this guy’s door and thinking, ‘What am I doing?!’ Then I walked in and he’s just got one massage table in this empty apartment and I was like, this is creepy, but I told him my story and he sat there and talked to me and it really helped me get through it and understand it. I remember him saying, ‘I know you think it’s your fault, but it’s not your fault. You’re not God. You can’t control people or tell people when it’s their time to go, so you can’t feel guilty because you don’t have control over that. This had nothing to do with you. If she wouldn’t have done it that night, she would have just done it another night.’ There was one thing that always stuck with me. He said, ‘Look, you were chapter 3 in her life. Chapter 1 was the root of the problem and you weren’t there for chapter 1 when she was a kid.’ I remember that and that really helped me and in her note she said, ‘You gave me the best 6 years of my life.’ She wrote that in there but it didn’t make sense to me when I read it at the time. There were too many emotions going on for me to really understand it. It wasn’t until he explained it to me in that way that it finally made sense.” Jim’s experience with the shaman was everything he hoped it would be and I was glad to hear that his message resonated with Jim because that was the truth. It wasn’t him who caused the damage. He was just there at the time when she gave up and I know it may sound weird but her third chapter was actually a happy one and she was lucky to have had Jim in her life to show her real love and happiness before she died. I’m glad he took that trip to see the shaman and was open enough to share his experience with all of us.
I totally commended him for everything he did to heal himself but nothing truly heals a broken heart better than new love and it turns out that the next relationship Jim had after this loss was the one he had with Robin Quivers. Jim said that Robin knew about his loss and was incredibly supportive of him during their relationship. It turns out that Florentine’s life has been impacted both personally and professionally by two of his biggest heroes, Howard Stern and Andrew Dice Clay. I still remember watching when MTV tried telling Dice that he couldn’t say half of the words in his set on the Video Music Awards and Dice went out there and told his jokes exactly the way they were meant to be told. Jim had a similar experience with Donald Trump’s show, The Apprentice and was hoping he’d tell me a little bit about what happened behind the scenes with that situation and he did! Jim said it was a live episode and whoever was still on the show was supposed to be putting together a corporate event so they booked a comedian to perform. Trump used to have a partner named George and George and his wife were sitting in the front for the show and they were very old. Then backstage, by the cameras, this guy was saying to Jim, “Don’t curse and whatever you do, don’t pick on George and his wife. They’re going to be in front but just ignore them and do your set.” As soon as Jim heard that he was like, “Please. I’m going right at George!” Jim went right out there and started making fun of George and was like, “Hey George, do you and your wife still have sex?” He said George was laughing but he had no idea that while he was doing his set, they kept cutting to the guy who told him not to make fun of George and he was screaming, saying, “What is wrong with this guy?! What is he doing?!” and that went out on live TV. Then the guy yelled at Jim afterwards and Jim was just like, “Hey, I’m a comic. You don’t tell me what to say. You tell me not to do it, I’m going to do it.” Jim didn’t care, he just thought it would be funny for the people watching at home. There have always been three comedians that I think of as rock stars; they are Howard Stern, Andrew Dice Clay and Sam Kinison… but after this conversation, I’ve added Jim Florentine to the list! He is a total rock star!
If you want to check out Jim Florentine’s comedy, he has a podcast on Barstool Sports called, Everybody is Awful and is the host of a hard rock show on SiriusXM called, Ozzy’s Boneyard. You can also catch him on the Kreeps with Kids tour as soon as this pandemic ends and trust me, you will not be disappointed!
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Sara Dahms
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