70 Hilarious Gilbert Gottfried Moments from His Friends and Family on What Would Have Been His 70th Birthday

Gilbert’s One-of-a-Kind Act

1) Richard Kind, Actor: When I was a kid, right out of college, that’s when I went to the comedy clubs. The first time I saw Gilbert was at The Improv at midnight, and he started doing the Ubangi lips with the round serving trays and the Mickey Mouse stuff with two trays on his head. He was doing jokes where he was defying the audience not to laugh and this excessive defiance was emblematic of his humor. He would start on something and just keep going. Years later, he did that on the podcast too. 

My favorite thing is when Gilbert would escalate, when he would really go into the bad boy and people would say, “Enough. Stop it!” And Gilbert just kept going. If you didn’t know who Lionel Atwill was, he didn’t care! The more Gilbert would do Lionel Atwill jokes. I tell you, that night when I first saw him, people were leaving until there were maybe seven people left, and I was dying. I was rolling over. He was defiant. 

2) Frank Santopadre, Comedy Writer and Co-Host of Gilbert Gottfried’s Amazing Colossal Podcast: My favorite Gilbert bit is the one where he goes through this long, drawn-out story about how he was walking through the country and a strange, alien ship landed in the field in front of him. Gilbert does this beautiful, dramatic acting — it’s like a one-act play — where he’s describing the ship and this latch opening and these greenish-grey creatures emerge and they surround Gilbert and one of the aliens opens its mouth and says, “Ben Gazzara is a good actor, why can’t he get a series?” 

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That is where I fell in love with Gilbert because that bit spoke to me on so many levels. I was sitting there with friends who had no fucking idea what he was talking about, but I was electrified because I was this guy who had watched those old TV shows and read those credits and obsessed over character actors — and here’s this guy onstage justifying my existence. I was just starting to think about going into comedy, so seeing him was transformative to me. I started following him to every club, and I would cheer on the regular bits like when you’d see Elton John and you want him to do "Bennie and the Jets.”

3) Lewis Black, Comedian: One of the things that truly stands out is, before I was a comic, I would go into Catch a Rising Star and see Gilbert. This was 1983 or so, and Gilbert would go on at the end and I thought he was unbelievable. He would pick up these two carry trays and do 10 minutes of improving with these carry trays! He slapped them under his arms and pretended he was in a wheelchair. And he kept doing other stuff with them, some of which would be considered “You can’t do that now.” But son of a bitch, it was funny.

4) Ron Friedman, Writer and Producer: Gilbert never sold out his material. He was famous for that. It didn’t matter if it was going over or not, he continued to drive it home. He’d say, “This is important! Please pay attention! A bear and a rabbit are taking a shit in the woods! The bear says to the rabbit, ‘Does the shit stick to your fur?’ The rabbit says, ‘No.’ So the bear wipes his ass with the rabbit!” Now, that should get a laugh, but if it didn’t, Gilbert would say, “What is wrong with you? Do you have something against rabbits?”

5) Frank Santopadre: In his act, he used say, “I wonder if people in the Middle Ages used to walk around going, ‘Wow, this is a really long time ago.’”

6) Billy West, Voice Actor and Frequent Howard Stern Show Guest with Gottfried: I always loved Gilbert’s stand-up act, and I got him immediately — it was my kind of humor. I love offbeat, and boy, how would you describe it? Surreal? Some of it was also appalling and funny. And that’s everything art is supposed to be. It’s supposed to evoke feelings. 

He did this one joke where he’s at a party and he found himself sitting next to Jacqueline Kennedy Onassis. He looked over at her and said, “You know, it’s funny, no matter who you are, you always remember where you were when…” Then he just stops. I mean, you can’t top that. It was the funniest thing I ever heard. 

7) Jackie Martling, Author of The Joke Man: Bow to Stern and Head Howard Stern Show Writer: Gilbert and I were doing a Carol M. Baldwin Cancer benefit. It was a golf outing and then the two of us told jokes at the dinner and we were both so dirty.

One of Gilbert's jokes was that a producer has a young, sexy, blonde actress over for dinner, and after they get done eating, he starts making out with her and he’s fooling around and then she says, “Excuse me, I’m going to the bathroom.” She left to go to the bathroom and he’s all excited. But she’s gone for a while, so he goes looking for her and she’s in his bedroom stealing all of his money and jewelry. He says, “I’m calling the cops, you fucking whore!” She says, “No, no, no, no, no! Please don’t! I’ll do anything!”

He says, “Take off your clothes.” And she takes off her clothes and he tries to get on top of her, but he can’t get going. She starts to suck his cock and nothing gets going. He’s got his fingers up her ass and nothing’s working. She’s eating his ass, and he just can’t get a hard-on. He’s doing everything he can and she’s blowing him and sucking his balls and licking his ass. Finally he goes, ‘Fuck it. I’m calling the police!’”

8) Frank Santopadre: Another great bit of Gilbert’s was, “If Nostradamus was so great, how come he didn’t predict Henry Winkler’s stardom? At the time, Nostradamus was saying, ‘Chachi I could see, but Winkler?’” Tying Happy Days to Nostradamus, he was a master of mixing elements. As comedy, it was Dada. I always said to Gilbert that he was a surrealist.

9) Judy Gold, Comedian: Gilbert was the only guy who would perform and comics would come to his show on a Saturday night and not do sets so they could watch him. You wanted to go with him wherever he went in his head. On stage though, nobody wanted to follow him. A joke is a surprise, and you can’t compete with Gilbert. There’s never going to be another one, it’s such a loss. 

Meeting Gilbert in Person

10) Drew Friedman, Artist of the Book Schtick Figures: The Cool, the Comical, the Crazy and Subject of the Forthcoming Documentary Drew Friedman: Vermeer of the Borscht Belt: I met Gilbert up at National Lampoon in the early 1980s. Lampoon was trying to revive itself so they hired a bunch of new writers, editors and artists — among them was Gilbert and me. So I went up to National Lampoon to drop off work and hang out, and I started realizing that this little guy Gilbert Gottfried was there, who I knew because he’d been on Saturday Night Live. He was very shy and quiet, but he knew who I was and he was a fan of my artwork, which, back then, I did with a stippling technique, which uses thousands and thousands of little dots for detail. So, we started talking and we discovered that we shared a love of old horror films, and we’d talk about them every time we bumped into each other.

One time, I went in there to drop off some work and Gilbert was there — I think he hung out there because there were a lot of pretty secretaries there. Anyway, he noticed me and started screaming, “Hey look! It’s JEW DOTS! What did you bring us, Jew Dots, a drawing?” He started screaming “Jew Dots” like it’s my nickname, and it stuck because every time he was there and he had an audience he'd start with, “Hey! Look! It’s JEW DOTS!” 

11) Frank Santopadre: Gilbert never learned my wife’s name. My wife was in his life for seven years. We were at his 60th birthday party. We went to his kids’ parties. We had dinner at his house. My wife took many, many cab rides with him and she went to every live show of the podcast. So Genevieve said to him one day, “Do you know my name?” and he said, “Of course I know your name!” She said, “What is it?” He said, “Uh… Toodles?"

12) Mike Reiss, Writer: In the 1990s, I used to throw a big Christmas party every year in L.A.  About 100 people I didn’t know would show up, including one celebrity. One year, Gilbert came. He was in a corner, scarfing hors d’oeuvres like he’d just got off a desert island, and I said to him, “Gilbert, I am a huge fan of your work. It’s an honor to have you in my home.” He replied, “You look like that gay man.” I said, “What?” “You know, that guy who’s in movies always playing the gay man?” he yelled, spattering my jacket with crumbs of food I’d paid for. “You look just like him.”

Gilbert and I became friendly over the years, and I adore his wife and kids. He was great company at lunch — if I paid. Once he even ordered a cake to go, on my tab. That seemed to be pushing it.  

As for that gay actor I look like, I guess I’ll never know. Maybe it was Franklin Pangborn. I hope it’s Tom Cruise.

Gilbert’s Legendary Frugality

13) Scott Alexander, Writer and Producer: How cheap was Gilbert? Back in the 1990s, we did the Problem Child films. There was also a Problem Child TV movie. There was even a Problem Child cartoon show. These projects were diminishing returns. The cartoon was the worst — absolute rock bottom. It was produced for pennies. Gilbert was the only actor who was in every version of this franchise. Everybody else got smart and bailed, but Gilbert kept taking the checks on a treadmill to hell as Mr. Peabody.

Twenty years later, Gilbert tracked me down. Now he had a couple kids, and he wanted to show them the shitty cartoon show. He asked me to send him some episodes. The show is awful, and I was astonished that he’d want to torture his kids with it. But, in any case, I explained to Gilbert that I didn’t have a closet of videos. I had nothing to send him, but I let him know that the old VHS's were still being sold on Amazon. They were dirt cheap — $3 each.

Gilbert says, “Great! I’ll take a few.” I said, “I don’t understand. You want me to order them for you?” He said, “Yes!” I said, “Gilbert, they’re only three dollars.” Then he said, “Here’s my address!” So, I had to buy Gilbert copies of the Problem Child cartoon and mail them to him.

14) Penn Jillette, Magician: One time, I ended up in East St. Louis in a whorehouse with Gilbert and a couple of hookers. Gilbert said to me, “Do you think they’d fuck me?” I go, “Gilbert, it’s kind of a hooker’s hippocratic oath. No matter how repulsive you are, they still have to fuck you.” He said, “Do I have to pay them?” I said, “Yes.” So, we ended up in bed with the hookers, but with our clothes on watching The Honeymooners until five in the morning. 

15) Dara Gottfried, Gilbert’s Wife: Gilbert was a bit of a hoarder. One time, we were traveling and I ran out of toothpaste, so I borrowed his. Shockingly, it was discolored and liquid. After checking the expiration date, I yelled to Gilbert, “Your toothpaste expired in the 1980s!” Of course, Gilbert said, “It’s still good!”  

This traumatic experience inspired me to suggest to our daughter to do her elementary school science fair project on whether toothpaste expires. It does, by the way, after 10 years, according to an elementary school kid. She won first place.  

16) Gino Salomone, Movie Critic and Hollywood Insider with Fox 6 Milwaukee: Tony Curtis released his autobiography, and Gilbert would call me from a book store and read a chapter a day to me in Tony’s voice. He was too cheap to buy the book, but he went there for five consecutive days to read me a chapter.

17) Frank Santopadre: He would only get into a cab with me if I offered to pay in advance.

18) Frank Verderosa, Audio Engineer of Gilbert Gottfried’s Amazing Colossal Podcast: At Nutmeg Studios, where we recorded the podcast, every room had jars that would have candy bars or peanut-butter-filled pretzels, or some of the big jars would just have bags of chips in them. Every time Gilbert came in, he would just dump it all in his knapsack and bring it home for his kids. 

19) Frank Santopadre: I remember when I showed up at The Friars Club to record the George Takei episode of the podcast and there was George and George’s husband Brad and Dara and the engineer, but no Gilbert. I said to Dara, “Why are you here and Gilbert’s not?” She said, “Well, I took a cab.” I said, “He wouldn’t get in the cab?” She said, “He wanted to use his bus transfer.”

20) Gino Salomone: At Gilbert’s birthday party, a great group of friends came out to celebrate. He walked around by himself and told me that he never had a birthday party before. I told him that he should mingle and enjoy himself and he said to me, “You think?” He didn’t seem able to accept this love from so many people. I also flew all the way from Milwaukee because finally Gilbert was buying dinner.

Outings with Gilbert

21. Howie Mandel, Comedian: Nobody made me laugh harder than Gilbert. I used to go to New York, and we’d go to the Carnegie Deli. The seating was such that, when we’d sit down, we’d inevitably be at a table sitting shoulder-to-shoulder with six people we didn’t know. The conversation would always start with me saying to him, “How are you doing, buddy?” and he’d say, “I don’t know. I have a — I think it might be an anal fissure.” He says this as a tourist an inch from his shoulder is just about to take a bite into their sandwich. 

And Gilbert would continue with, “The thing that’s bothering me is the seeping and the puss. I don’t know what it is. I tasted it, and it’s got a sour taste that made me throw up.” It would go on and on for 10 minutes, the most horrific, loud exchange. You have to imagine Gilbert doing this at a table in a public place within earshot of at least 30 people trying to enjoy their lunch, and I’d be crying. I never laughed harder, and he did it so many times in public places just to horrify people. That’s something I shared with him — there’s nothing funnier than people being shocked and horrified — and he was the king of horrifically funny, shocking comedy.

22) Penn Jillette: We were having a high tea at the Waldorf, and it had been reported that the guy who played Eddie Munster had been mugged. Gilbert did about three or four minutes of his impersonation of the muggers talking about how they were going to “Get that Munster money.” “We’re gonna get that Munster money. That’s serious Munster money. That’s Eddie Munster. We’re going to get that serious Munster money.” I remember actually spitting tea all the way across the table. I couldn’t control myself. I was helpless.

23) Neil Berkeley, Filmmaker and Director of the Documentary Gilbert: I’d already been working on my documentary about Gilbert for several weeks, but the first time that I think Gilbert recognized me as something other than furniture came on a trip to Philadelphia.

I called Dara and said, “I want to go on the road with Gil.” She said, “Okay, he’s going to Philadelphia in a couple of weeks. You’ll have to get a ticket for the Megabus.” Now, I’m not from New York, so I didn’t even know what the Megabus was, so I said, “What’s that?” and Dara says, “He takes this bus to Philadelphia because he doesn’t want to fly and spend the money. Don’t tell him this, but you need to get a VIP ticket up in front because I want him to sit in a nice seat and look out the window. But don’t tell him because he’ll be mad that I spent the extra $10 for that seat.”

The day comes, he gets on the bus and says, “So we’ll do a couple of shots and we’ll put the camera away, right?” I said, “Sure.” Besides that, he doesn’t really talk to me much, and he didn’t really want me around. So I’m sitting there and this girl gets on and she’s really pretty and she sits down next to me, so I figure I’ll talk to her. I talked to her for the entire two-hour ride and Gilbert didn’t say a word the whole time. Then we got off the bus — and usually he’d just walk away from me and not acknowledge my existence — but this time he said, “Hey, why don’t you give me your phone number in case something happens and I need to call you?” I thought, that’s weird. 

But I gave him the phone number, and, sure enough, I get back to my room and he calls me and he’s real chatty. “What are we going to do tomorrow? Where are we going to lunch? What time are we going to the club?” Finally, there’s this long silence, and he says, “Okay. I’ll see you tomorrow” and I said, “I’ll see you tomorrow” and he says “Okay” and another long silence. Then he goes, “So, are you gonna fuck that girl from the bus?”

24) Drew Friedman: I lived in a tenement apartment on East Sixth Street, and Gilbert’s mother lived two blocks away. Gilbert knew where I lived, and, one day, the buzzer buzzed. I wasn’t expecting anyone, but it was Gilbert. I let him in, and I said, “Hey, how are you doing?” and he said, “Hi.” Then he walked upstairs to my apartment, took off his coat and said, “Can I watch some of your horror films?” because I had a VCR and he didn’t. I said, “Yeah, sure, sure. Sit down.” 

I sat him down and gave him a glass of milk and he watched some of my old horror films from my collection, then he just left. Once he came by the first time, he came by again and again — and he never called ahead of time. I’d put these movies on, he’d watch one or two and we’d sit there in silence. Sometimes I watched them with him, and sometimes I had to work because I had a deadline, so I’d just sit him down at the couch, he’d watch the film, then it would end and I’d help him put his coat back on and he’d leave. Or, my wife would come home from work and wonder what he was doing there and I’d say, “It’s Gilbert Gottfried, he just wants to watch Plan 9 from Outer Space.”

Gilbert on ‘Hollywood Squares’

25) Gino Salomone: One of Gilbert’s great honors was when I told him that I had brought his name up to Henry Winkler, and Henry said to me, “Gilbert wants to take me down roads that I will not go down.” Gilbert thought that that was a great honor for Henry to say that.

26) Henry Winkler, Actor and Executive Producer of Hollywood Squares: Michael Levitt and I co-executive produced Hollywood Squares for two years, and one of the smartest things we did was put Gilbert in the bottom end square. Now, that show was written within an inch of its life, but Gilbert wrote almost everything on the spot. I’m telling you, it was a miracle. He would say the most outrageous things so quickly, and it was all him. People just loved him too because he was so original. His voice was original, his soul was original and his wit was original. 

27) Bruce Vilanch, Writer and Celebrity Panelist on Hollywood Squares with Gilbert: On Hollywood Squares, there was this episode where the contestant kept getting it wrong with the same square, Gilbert’s square, over and over again. The game was tic-tac-toe and you had to agree or disagree with what a celebrity said, so you had to figure out if a celebrity was trying to help you or not. 

In one show, I remember there was this poor woman who wasn’t terribly sharp, and she kept having to go back to Gilbert. The second time she got it wrong, Gilbert shouted, “You fool!” and after that, he just kept hammering this poor woman, saying, “You fool!” over and over again. By the time she finally got a right answer, all nine of us were going, “You fool!” That moment is the single most memorable thing about that iteration of Hollywood Squares.

Gilbert’s Best (and Worst) Roles

28) Weird Al Yankovic, Singer and Songwriter: Even though Gilbert was always one of my very favorite stand-up comics, I knew better than to ask him to open for me. I try to do a pretty “family friendly” show, and I was aware that if you asked Gilbert to “tone it down,” he famously would go hard in the other direction — just ask Belinda Carlisle.

I had a Saturday morning network kids’ show in the late 1990s (The Weird Al Show on CBS), and one of my favorite bits was when Gilbert made a cameo appearance as my “imaginary friend.” He’d stand next to me and get more and more flustered as I pretended not to see him (“I’m here! I’m right here! I’m right in front of you!!!”).

29) Sarah Silverman, Comedian: Gilbert and Dara’s episode of Wife Swap (with Alan Thicke and his wife) is amazing. It’s must-watch TV.

30) Jackie Martling: Gilbert and I did a show together once called The Watcher; it was terrible. In the two or three days that we did that, we just hung out and told jokes. We were in our trailer one day, and Gilbert did a half hour of Ed Sullivan after Jackie Mason gave Ed the finger on The Ed Sullivan Show. Sullivan called Jackie Mason into his office and tore into him, “You Jew bastard. Who do you think you are? You could come on my fucking show you little cocksucking k*ke motherfucker.” It was like a one-minute bit that Gilbert did for 30 minutes. 

31) Frank Santopadre: None of Gilbert’s TV or film roles really capture him fully because nobody knew how to cast him and let him run with something, but I’d say, even if it’s the obvious answer, Iago in Aladdin is his best role because it’s the most Gilbert you get. It’s his most expansive role, and it gave him the greatest opportunity to show off his talents.

Gilbert at the Infamous Hugh Hefner Roast

36) Jackie Martling: I was there when Gilbert did the Comedy Central Roast of Hugh Hefner, which was only a couple of weeks after 9/11. He joked: “I have to catch a flight to California. I can’t get a direct flight, they said they have to stop at the Empire State Building first.” Now, that was a variation on an old joke, but I love the balls of him for saying that.

37) Sarah Silverman, Comedian: For the Comedy Central Roast of Hugh Hefner, it was terrifying getting on a plane barely a month after 9/11, but I’m so glad I did. Gilbert going up last after the roastiest of all roasts and just wiping the table up with all of us was a revelation. His telling of what became the most famous telling of the classic (inside baseball for comedians) “Aristocrats” joke was epic. And, in his own way, he honestly helped to heal all of us after 9/11. 

He just went so far with it! And we needed it. At least I did.

38) Penn Jillette: The movie The Aristocrats makes it seem as though the movie was made because of that moment where Gilbert told “The Aristocrats” joke at the Hugh Hefner roast. But in reality, we had already been working on the movie, and Gilbert and I had talked for hours and hours about “The Aristocrats.” And, before that I roast, I told him that if something doesn’t go over, “You can always do ‘The Aristocrats.’” 

Of course, Gilbert knew that his 9/11 joke wasn’t going to play, so he had “The Aristocrats” loaded, and I was ready to get it for the film. Still, it had no less emotional catharsis for the people there. 

Gilbert vs. the Tsunami

39) Judy Gold: Some of the funniest things he ever said were those tsunami tweets (when the Japanese tsunami hit in 2011). That fucking cracked me up. 

When the tsunami hit, Twitter was new and Gilbert posted these jokes not knowing what Twitter really was. He found out he was fired from Aflac while he was watching the news. The best part was one of the newscasters was reporting about the tsunami, and he ended with, “And to make matters worse, Gilbert Gottfried made these offensive jokes.” Gilbert was like, “I made matters worse? I didn’t know I was so powerful!” 

40) Lewis Black: The great thing about Gilbert is that he crossed a lot of lines. He and Bob Saget had this thing to them where there was this kind of sweetness to them while they were delivering some of the most disturbing things I ever heard. And it made it funnier!

When the tsunami thing happened, it was the equivalent of being hit by a car and not looking both ways. Gilbert didn’t realize that he was in the midst of a social media revolution — nobody did! And so, he sent some jokes out — not to a billion people, but to people he thought he was talking to — and people came after him.

They came after him by saying, “This is appalling! Let’s look at it again! This is appalling! Let’s look at it again!” It was like Janet Jackson’s tit at the Super Bowl; they couldn’t show it enough. So they were at fault! Not Gilbert. Gilbert wasn’t out there to make a million bucks off this — Gilbert was Gilbert. He saw it, he had that dark comedy streak and we were right at that turning point in comedy where all of a sudden you could make a comment about comedy. You laugh or you don’t laugh, you fuck! 

That enraged me because it was hard for him. He had a family, and, at this point, he didn’t like going on the road a lot. He didn’t have the luck that I did to be able to play theaters at that point even though he was a legend. I thought, that fucking duck, you’re taking away an income from someone who needed it. That Aflac fucking thing. 

Gilbert Gottfried’s Amazing Colossal Podcast

41) Frank Santopadre: The only reason the podcast happened was Gilbert’s agents at William Morris were having trouble booking him because the club owners had seen him doing the same act over and over again for years. They’d say, “Why is he doing the same act? By the way, it’s 2010, and he’s making references to Fantasy Island and telling Joyce DeWitt jokes.”

They were getting very frustrated with him and the agent called Dara and said, “He really needs to write new material,” but the more you told Gilbert to do something, the more he rebelled against doing it. So Dara said to Gilbert, “What if I got you a writer? What if I got you somebody you trusted?” And Dara knew me and asked if I could sit and work with him.

I was very flattered by the offer, but I knew he wouldn’t pay me. She said, “I’ll pay you. Don’t worry about that.” But then I thought, “How do you sit in a room with him and write these things that can only come from his brain?” So we got on the phone together, and it quickly became clear to me that he wasn’t interested in that process. He only did it because his wife and his agent were forcing him to do it. 

So, I thought, “What if we free associate?” If we start talking about Norman Fell and Hogan’s Heroes, maybe the jokes will come. The jokes never came, but the conversations went down these crazy rabbit holes where we’d try to out-do each other with more obscure character actors and more obscure references from different episodes and we’d stay on the phone for hours laughing. And this guy — who I never could get to know me or know my name or pay any attention to me or even shake my hand — was suddenly on the phone with me for four hours talking about Mr. Ed.

From that, Dara got the idea that these phone calls could be harnessed into something, that there was value in them. The phone calls became the podcast.

42) Dara Gottfried: Our podcast, Gilbert Gottfried’s Amazing Colossal Podcast, was a big part of the last eight years of Gilbert’s life. Gilbert’s co-host, Frank Santopadre, would spend countless hours preparing for each episode and showing up with a dozen “blue cards” of notes. Gilbert, on the other hand, would scribble a few words on toilet paper. He also never wrote down his jokes. As a record of his act, he just left us with a few sheets of paper with one word for each bit. Somehow, he stored all of this unbelievable knowledge in his brain. Luckily, we have recordings of these incredible interviews and his stand-up, which will live on forever.  

43) Frank Santopadre: Dara had proposed the idea of us doing this podcast, and I said “Sure let’s do it, but let’s not interview other comedians because so many of those shows already exist. Let’s see if we can interview showbiz legends. We’ll do the podcast equivalent of The Love Boat.” 

So, we go to (comedian) Professor Irwin Corey’s house, which his son sets up for us, and we walk into the living room and Irwin Corey is well over 100. He’s under a blanket and on a recliner — at this point in his life, he was half man, half chair — and we set up our mics, then we’re sitting at the coffee table interviewing a dead man. 

It was also the first episode, so I was trying to lay back in the sidekick role — I’m Ed McMahon, I’m not supposed to drive — but Gilbert isn’t driving either! He isn’t talking! So I’ve got a guest in and out of consciousness and a host who’s barely saying anything! I would say things like, “Gilbert, what was your first experience with the Professor?” and, occasionally, Irwin Corey would say something intelligible and then nod off. So, we finished the show, walked to a pizzeria — which Gilbert called a “pizza store” — and he looked at me and said, “Well, that was fun. We tried it.” 

That was the end of the podcast until Dara and I figured out that we needed an automatic guest, someone where you can be on autopilot and the guest would just deliver and that was Dick Cavett. That’s when we realized that we had a show. We ended up doing over 600 episodes together.

44) Frank Verderosa: The running joke for every episode was that Frank (Santopadre) would have this well-researched stack of cards while Gilbert would maybe show up with a crumpled up piece of paper in his pocket with a few things that he wanted to mention. That was always hilarious, but on one particular night when Richard Kind was the guest, Frank had forgotten his cards and we were almost not going to do it. I said, “Why don’t you just let Gilbert wing it?” So, in the introduction, Gilbert just made up a bunch of stuff about Richard as the opening, and Richard played along with all of it.

45) Frank Santopadre: There was the Bob Costas episode of the podcast where Gilbert came up with the idea of telling a dirty joke while Bob does color commentary, like a sportscaster (which he is). So Gilbert begins telling this really filthy joke and Bob does a cleaned-up color commentary interpretation of the joke. But, at one point, Gilbert got so filthy that Bob waved goodbye to me, got on his hands and knees and crawled across the room to try to crawl out the door. Gilbert was working so blue that it wasn’t good for Bob’s brand.

46) Patton Oswalt, Comedian and Actor: There are literally a thousand different moments from Gilbert’s stand-up or movie career I could choose, but there’s a moment on his Amazing Colossal Podcast that always destroys me and cheers me up.

My friend, Tom Scharpling, was the guest. He had just been let go from the writing staff on the HBO show Divorce, and Gilbert is doing his intro, and he mentions all of the amazing stuff Scharpling had done in his career — it was this huge buildup as only Gilbert can do. And then he says, “And today is his last day on Divorce. He’s no longer working on Divorce.” And then he proceeds to go on and on and on about how well Divorce is doing, and that you shouldn’t mention it to Tom, and he just reduces Tom to helpless laughter. I remember talking to Tom after that, about how bad he was feeling about the show Divorce, and how Gilbert brought him out of the funk with his intro. 

I know someone on this list is going to mention that cathartic moment at the Hugh Hefner roast where Gilbert joked about 9/11 and brought a lot of us, universally, out of this dark funk, but I’m also glad there’s audio evidence that exists that Gilbert could perform that magic on a one-on-one basis.

47) Frank Santopadre: When we had Steve Buscemi on the show, it was clear that Gilbert didn’t know that much about him. The memorable line that Steve said was, “I love how Gilbert has only a passing knowledge of my career.” The funny thing about it was, afterwards we went to The Friars Club and we had a wonderful lunch together. Gilbert opened up and Steve opened up, and the lunch was better than the episode.

48) Frank Verderosa: I remember when Jonathan Katz was on the show, and for whatever reason, Gilbert had a giggle fit. Every time Jonathan started to try to move forward with this story about David Letterman, Gilbert would just burst out laughing. Then Jonathan was laughing, and none of us knew what was so funny. Jonathan never even got through the entire story. I got Jonathan to tell me the story later and it wasn't even that funny of a story, but it's one of those moments with Gilbert where it was just insanity.

49) Frank Santopadre: When Matthew Broderick came on the podcast, Gilbert decided to tell him he hated Ferris Bueller's Day Off. Matthew Broderick was doing a show downtown, and he was between rehearsals. He graciously got into a car and came uptown to give us an hour and a half of his time. We weren’t paying the man, he is a star and he’s there, giving us his best and Gilbert says to him, “I fucking hated Ferris Bueller’s Day Off,” and I could see Matthew wilt a little bit. You can hear it in the show. He goes, “Oh, really, why?” and Gilbert doubles down on what an arrogant, insufferable little prick the character is. I wanted to unscrew a grate in the floor and crawl into it.

50) Frank Verderosa: Any of the episodes where Gilbert sang along with a guest was a lot of fun. Gilbert’s timing was always off, but I made no effort to clean any of that up because that was the fun of it all — how chaotic it was. The podcast at its very best was when Tony Orlando, Gilbert, Frank and Dara all joined in singing “Tie a Yellow Ribbon.” It was just magic. A lot of people cite that episode as they’re favorite, even if they’re not big Tony Orlando fans.

51) Mario Cantone, Comedian and Actor: I looked forward to doing the Amazing Colossal Podcast Christmas episode every year, and Frank Santopadre was a big part of that. He made both me and Gilbert look very good. I’m lazy and Gilbert wasn’t much of a preparer either, so we’d fly by the seat of our pants. That’s why we worked so well together; we didn’t write shit down, we just did it. 

We did a lot of fun stuff like “The 12 Days of Christmas” as all of our favorite impressions that we did, and everybody loves the “Baby, It’s Cold Outside” with me as Betty Davis and Gilbert as Tony Curtis. I think that was my favorite too. 

Melodically and rhythmically though, Gilbert wasn’t a musical person, which is shocking because he’s brilliant comedically and comedy is music. I was always like, “Stay on the beat! Stay in the pocket of the song!” But Gilbert would come in late and back-phrase and front-phrase. What a mess! Still, I loved him very, very much. 

Gilbert’s Favorite Celebrity Gossip

52) Neil Berkeley: Gilbert loved celebrity gossip; he read People and Us magazine. One day while I was filming the documentary, we were sitting there quietly, and I said, “Gilbert, have you ever seen the picture of Marlon Brando blowing Wally Cox?” And he perked up and he goes, “They have this photo?” I said, “Yes,” and realizing I could just Google it, I said to him, “You want to see it?” and he says to me, “Yes! What the fuck is wrong with you?” 

53) Richard Kind: On the podcast, whenever he got into Danny Thomas shitting on the glass coffee table or Cesar Romero getting orange wedges thrown at his ass, that was the best. There was one time where he got into the Danny Thomas thing, and I literally had to pull over on the side of the road because I was laughing so hard. 

54) Bruce Vilanch: I met Gilbert first at The Comedy Store. He was very funny, and he had a fabulous reputation as having the largest penis among the comedians. Every waitress would attest to that. I relayed this on his podcast, and while Gilbert didn’t deny it — who would? — he did show some rare modesty.

55) Richard Kind: When, because of a Quincy Jones interview, Gilbert found out that Marlon Brando and Richard Pryor might have fucked, he took such delight in that.

Some Sweet Gilbert Stories (For Balance)

56) Dara Gottfried: Gilbert had a way with words. For every anniversary and birthday, he would leave me a dollar store greeting card taped to the bathroom mirror which always included, “Go fuck yourself. Love, Gilbert.”  

57) Gino Salomone: I went out with Gilbert and Dara for their anniversary. Gilbert was his uncomfortable, miserable self, and I made him hold Dara’s hand and look in her eyes and tell her that he loved her. She loved watching him squirm, and he finally did it. I was honored to celebrate their anniversary with just the three of us. It was so romantic!

58) Dara Gottfried: Although his public persona was loud and obnoxious, he was quiet, sweet and shy in his personal life. We lived across the street from the School for the Blind. He often offered to help the residents cross the street, and he loved to come home and tell me whenever he did. He was just the sweetest.   

59) Richard Kind: I remember as we were both getting older, we were going down the stairs one day and he was on one side holding a banister and I was on the other side and I said, “I can’t believe that I use banisters now to hold onto when I go down the stairs.” He goes, “Yeah, I always thought banisters were for sliding down. Who knew that we had to use them sometime.”

60) Dara Gottfried: Gilbert used to say he was like a McDonald’s Happy Meal. You can’t swap the french fries for onion rings. He wasn’t going to change. After 10 years of dating, he finally went along with getting married and having kids. He was still true to himself, but a better version. He was very happy and the most amazing father and husband. 

61) Weird Al Yankovic: I’ve had a number of close friends in the comedy community pass away in the last few years, but for some reason Gilbert’s death hit me particularly hard. He just struck me as the kind of person who was never going to die. Gilbert was without doubt one of the funniest people I’ve ever known. I was lucky enough to be a guest on his podcast, and I just remember laughing my head off the entire time. He was fearless, and on another wavelength entirely. I really, really miss that guy.

62) Penn Jillette: Gilbert was a very, very close friend. I spent a lot of time with Gilbert, and I’m still very close to Dara and (their kids) Lily and Max. He meant the world to me. The story I’ve only told once kind of publicly is perhaps too serious and too odd for this, but I’ll tell it because it’s so perplexing to me. 

Gilbert and I were both mama’s boys; we’re very, very close to our moms. And my mom died about a year and a half before Gilbert’s mom. And, when Gilbert’s mom died, he was — as I was when my mom died — devastated. So, I came to New York to be with him, and it was one of the oddest evenings of my life. We went to a place in New York called Cafe Un Deux Trois and we got a table in the back, and I don’t know what happened, but Gilbert and I just started telling offensive jokes. 

Now, I don’t mean offensive like the ones Gilbert told. I mean really offensive. I mean, outside of my morality and outside of Gilbert’s morality — any one of these jokes would get us canceled permanently. We told them back and forth for three hours. We never talked about our mothers. We never talked about death. We never talked about life. We just spilled our guts out with the most pure hate I’ve ever experienced. And it was completely cathartic. It was some sort of trust exercise or some sort of ranting against life and against the world. It was one of the weirdest things. I mean, that’s not one of the five stages of accepting death. There’s not a grief counselor that says, “Why don’t you get together with a friend and tell jokes that make you sick?” But that’s what we did, and it was really, really cathartic.

Gilbert Meets the Nazis

63) Steve Stoliar: I first saw Gilbert in 1982 when I moved to New York to write for Dick Cavett. My roommate took me to The Improv and I wasn’t familiar with Gilbert, but Gilbert came out and just started doing all these hysterically outrageous things about Jews and Nazis and character actors. It was one of those times when I worried that I wouldn’t have sufficient time for my lungs to reinflate before I passed out from laughing, which it’s a great feeling and a scary feeling because you get to the point where you’re almost lightheaded because you’re not getting enough oxygen. 

64) Frank Santopadre: One of my favorite bits of Gilbert’s was about former U.N. Secretary Kurt Waldheim. Waldheim was rumored to have had a Nazi past and the bit reaches a point where the Jewish Defense League is chasing Waldheim through the streets and Waldheim runs up these steps to the roof of a building and the JDL guys grab a bullhorn and shout, “Come on down, Waldheim!” and Waldheim yells down, “No, no, no! It’s me, beloved character actor Norman Fell!” Then the JDL members say, “Okay, but how do we know you’re Norman Fell?” Waldheim yells down, “John Ritter was the consummate professional!” and the JDL guy turns to his associate and says, "Hm, he does sound like Norman Fell.”

And the bit just goes on and on like that, and it was so out there. Why I love that bit was because Gilbert takes something in the news — that Kurt Waldheim was accused of having Nazi ties — and he marries it to Three’s Company. The wedding of those two ideas really describes his brain.

65) Jeff Ross, Comedian: We were doing a Netflix historical roast, and we roasted Anne Frank. I got some pretty funny jokes together and I needed someone to play Hitler, so I called Gilbert’s agent and he hung up on me. But I didn’t want to take “no” for an answer, so I called Gilbert directly and I said, “Gilbert, I need somebody to play Adolf — ” I didn’t even get “Hitler,” out and he goes, “I’ll do it!”

He shows up a week later for the shoot and for rehearsal we have to put him in some of the wardrobe. There was lederhosen and knee-high socks and a Hitler mustache and we combed his hair off to the side and we put the swastika armband on him. He was the cutest Hitler. 

He wore it to rehearsal. Then he wore it on the show. Then, at the afterparty, he still had the mustache and the armband on. I’m pretty sure he wore it on the flight home the next day. He was the best Hitler ever. Really, what a great way to roast Hitler to have the loudest most obnoxious Jew in history portray him.

66) Neil Berkeley: In the documentary, if you haven’t seen it, there’s this really interesting moment in the film where he and I went to this place outside of Chicago called the Pheasant Run Resort. It’s this massive resort with a hotel, a club and a convention center. We go there and we’re checking in and we keep seeing these people in military clothes. I asked him if he wanted to check out the military thing. So, we’re walking in and Gilbert's looking at the paraphernalia and he sees Nazi knives and patches and stuff and he’s laughing his ass off. Then we look over and see people dressed in full Nazi costumes and Gilbert’s laughing. Then they see him and they come over and they’re taking photos with him and Gilbert’s like, “Boy, the Nazis really love me.” 

What you don’t see in the movie is that I invited those guys to Gilbert’s show that night, and I put their names on the list. I didn’t know they would go to the show in costume. So they’re sitting in the back of the room under this red neon light like a scene out of Cabaret. Gilbert didn’t know they were there though until after the show, because he would always go out after the show and sell DVDs and sign autographs.

While he’s doing that, I spot one of the guys in the Nazi uniforms outside, swinging his nightstick around, and I tell Gilbert to take a look. So, I’m getting the shot of Gilbert looking out the window when I look up and another Nazi is walking toward Gilbert in the background. Now, this is one of those moments where I think, “Do not blow this shot.” So, Gilbert is looking out the window, laughing at the guy outside, then he turns around and sees this other Nazi a foot away from him and Gilbert jumps back and yells a little. Then, the guy in the uniform tells Gilbert this terrible Michael Jackson joke. The joke is so bad he apologizes for it, and Gilbert says, “That’s not the worst thing the Nazis have ever done.” Gilbert laughed for two hours after that. We went back to his room, and he couldn’t stop laughing. 

Now, Gilbert never signed his agreement to be in the movie. I made the whole thing, it was accepted at Tribeca, but he could kill the whole thing if he just said, “No. I don’t want to sign that.” It was a huge risk. The first time he sees the movie he watched it with his family, they come out and Dara is crying and Gilbert’s sister, Arlene, was so happy. Then Gilbert walks up to me and all he says is, “Boy, those Nazis were a gift from God. “

Gilbert the Legend

67) Whoopi Goldberg, Comedian and Actress: Gilbert was a really good friend. We spent time together on Comic Relief and lots of other things and he was always funny. He was a singular comic. There was no one like him. That’s what I take with me when I think about Gilbert.

68) Penn Jillette: If you think about Gilbert on Howard Stern or Leno or those kinds of things, you tend to think of him as a strong character doing jokes, but there was a lot more going on. 

Everybody talks about repeating things until they’re funny — they’re not funny the third time, but they’re funny the 15th — but what Gilbert did was more complicated than that because there was a meta-timing of it. Instead of the timing of his jokes being within the sentence, his timing could be the repetition of the sentence. There was a really interesting rhythmic thing going on with Gilbert.

I saw him do this in 2015 in Vegas with a predominantly young audience and he was doing Al Jolson jokes. I don’t think anyone understood the references, yet the audience was convulsing in laughter. You could say that he’s a funny character with a funny voice, but there’s more to it than that also.

People often say that one of James Brown’s many contributions to music was realizing that everything, including the vocal, could be a percussion instrument. With Gilbert, it was a very similar thing. I put Gilbert in the category of Picasso, Stravinsky and Miles Davis. That’s the level he was working at. He wasn’t the funniest person of the late 20th century — that’s damning with faint praise — he was creating another art form. The way he built the rhythm of his jokes and the way he built the rhythm of his act was as revolutionary as “The Rite of Spring.”

69) Frank Santopadre: Gilbert was a guy who was on the spectrum, who had no ability to shake my hand, look me in the eye, learn my name or connect with me in any kind of real way. He had no social skills.

And with that, I went through several phases with Gilbert, from being the kid in the audience thinking he’s the greatest comedian I’ve ever seen, to following him around like a puppy for years. When I started to get a foothold in TV, he kept showing up on shows I was working on and I worked with him many times — I even wrote jokes for him at roasts and went over them with him extensively — but he would never remember my name. I’d say, “Gilbert, do you know who I am?” and he’d say, “Yeah, you’re the guy in the blue striped shirt” and I look down and I’m wearing a blue striped shirt.

Then I got to be on this amazing ride with him. We did 600 podcast episodes together and still, there was a part of me that thought, if he didn’t pass away and we ended the show and five years went by, I’m not sure if he would have known me. And it wasn’t a bit — I wish it was a bit — it wasn’t. 

Anyway, that’s what I said at his eulogy. I closed by saying, “Gil, if there is something after this and if we should ever meet again, I hope you’ll remember my name.”

70) Penn Jillette: The problem with telling stories about Gilbert saying something hysterical is that Gilbert's style was so purely distinct that the stuff that I can tell you that made me spit tea across the room is stuff I can’t even pretend to translate. So, when you’re putting this all together, just make sure you say he’s the funniest person that was ever in our lifetime, because it’s the most important thing to say.