Let's Look Back At All Of The Roast Sets From Greg Giraldo, The Best Ever
I compiled all of Greg Giraldo’s televised roast sets in this post. It’s an absolute crime that you can’t find all of his sets in one place, or at all really. Luckily, I saved all of them a few years ago and decided to load them up for everyone to watch.
Greg Giraldo was a genius comedian. Seriously, the guy was insanely smart. He graduated from Columbia University and Harvard Law School before deciding to take up a career in comedy. He had a near perfect score on his LSAT, but ended up trying to make people laugh instead. His tragic death in September 2010 was felt across all of comedy. It never felt like Giraldo got the respect he deserved, and his TV show projects always seemed to burn out quickly, even with so many friends in the industry referring to him as one of the best ever. He died of a prescription medication overdose after struggling with drugs and alcohol his whole life. It’s a sad, sad story and unfortunate that such a great mind was never really able to break away from his addictions. Regardless, he should be celebrated as one of the most underrated comics to ever live.
I personally (making this about myself for a second) deal with some mental health issues and find that comedy is a great way to shut my mind off and have no worries. Giraldo helped me through some tough times with his insane on-stage realism, well thought out and smart jokes and, of course, his roasts. It never felt like he was trying on stage. He was real, raw and just flat out fucking hilarious. His death was one of the first celebrity deaths that truly upset me. The fact we will never hear him make new jokes again is such a shame. A documentary about Giraldo aired on Comedy Central after his death and made it a point that he was not “just an insult comic,” and he wasn’t. His stand-up routines are must-listens. With that said, his roasts are still some of his best work and they need to be on the internet for all to see.
Below, you will find each full roast set from his 10 appearances, a few of my thoughts, as well as some of my favorite jokes. I hope you enjoy. Rest in peace, Greg.
The New York Friars Club Roast of Chevy Chase (2002)
This is the shortest of his roast sets, but Giraldo is still great. One of the best parts of all of his sets is him getting a quick jab in at the roast master right after being introduced. It was always weird to me how uninterested Chevy Chase was here and Giraldo played right into that with some digs at Chase’s career.
Favorite Joke
Giraldo: “Your show lasted six weeks. Sarah Jesse Rafael’s lasted 16 years. That’s got to feel good, late at night, huh?”
Sarah Jessy Raphael: “20!”
Giraldo: “Ah fuck you, I chopped off four years for symmetry, shut up.”
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The Comedy Central Roast of Jeff Foxworthy (2005)
Letting all four of the Blue Collar Comedy Tour sit right next to Greg Giraldo during a roast is like lobbing him a pitch right over the middle of the plate. You could argue this was Giraldo’s best roast. It always felt like Giraldo took it a little personally that the Blue Collar guys were far more successful than him and that his digs held a little truth to them. I wish this set had been longer.
Favorite Joke(s)
“Good to see Bill Engvall here. Bill, he’s a prolific bastard, man. He’s got seven comedy CDs out. Without Bill, Sears would have no comedy section. Seven CDs. Bill, did you ever think of just saying something unfunny without recording it?”
“Jeff [Foxworthy] has always been an original and an innovator. Back when everyone was doing corny observational comedy, Jeff came up with the idea of doing it in a Southern accent.”
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The Comedy Central Roast of Pamela Anderson (2005)
This is the first dais that was expanded with a ton of people and it gave Giraldo even more opportunities to go after people. He goes in on Jimmy Kimmel, Adam Carolla and Sarah Silverman with some real killer jokes. The Carolla jokes alone about Pete Sampras and water-proofing his deck got some of the biggest laughs of the night. He had some great jokes about Pamela Anderson, too, and you could tell he had a fair amount of respect for her success. Also, can’t go without mentioning how much of a disaster Courtney Love was that night.
Favorite Joke(s)
“Good to see Eddie Griffin. Of course Eddie Griffin. People said there wouldn’t be any big movie stars here tonight, and they were right.”
“You’ve [Pamela Anderson] been flattened out and re-inflated more times than Jeff Ross’ prom date.”
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The Comedy Central Roast of William Shatner (2006)
Again, Giraldo was a genius here in finding a way to tie in all of the people on the dais, even if they didn’t all have connections. It also helps when the person being roasted, William Shatner in this case, connects well with the roaster. I think a roaster having respect for the roastee helps make the set even better. Any time someone can make fun of Andy Dick, sign me up.
Favorite Joke(s)
“Look at this dais, fat guys, old ladies and an Asian. I feel like I’m on a bus to Atlantic City.”
“Look at this, Nichelle Nichols, Farrah Fawcett and Betty. Uh, I’ll take ‘Women I Would Masturbate to 30 Years Ago’ for $1,000, Alex. What a cruel joke, three women you’d want to fuck 30 years ago and one I wouldn’t fuck 30 beers from now [points to Lisa Lampanelli].”
“[William Shatner] You’re a humanitarian, you work with a foundation to bring peace to the Middle East. Whatever it is you’re doing, keep it up, because it’s really working.”
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The Comedy Central Roast of Flavor Flav (2007)
This is my favorite roast to ever air on Comedy Central. I also think this is clearly Greg Giraldo’s best set; every single one of his jokes is on another level of funny. Other roasters were great as well, especially Jimmy Kimmel, who I posted a bonus clip of below. Giraldo’s Katt Williams jokes still make me laugh out loud to this day. In the Greg Giraldo documentary, they mention how they knew that the reaction from Ice-T to the record deal joke about him confirmed how great the set was about to be.
Favorite Joke(s)
“[Katt Williams] What a teeny little pimp! Man, being a pimp ain’t easy, especially when you gotta stand on phone books to smack a bitch.”
“You are a big ghoulish woman… I’m talking to you Carrot Top.”
“Jeff Ross just hosted some ridiculous talent show on ABC. A talent show, where do you get the balls to host a talent show? You running a talent show is like Michael Vick running the ASPCA.”
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The Comedy Central Roast of Bob Saget (2008)
The Roast of Bob Saget was another Top 3 Comedy Central roast thanks to Giraldo and the infamous “on-purpose bombing” from Norm MacDonald. Bob Saget probably laughed the hardest out of any of the people Giraldo roasted over the years. The Anne Frank joke about Lovitz was killer and Cloris Leachman’s reactions to her roasts were fantastic.
Favorite Joke(s)
“John [Stamos] was married to my favorite supermodel, Rebecca Romain O’Connell. John, you lost your wife to the fat kid from ‘Stand By Me’.”
“Norm [MacDonald] has a giant gambling problem. He’s dropped more coin at a casino than Michael J. Fox at a parking meter.”
“We’ve all seen you shirtless [Brian Posein] on the ‘Sarah Silverman Show’. It’s hard to believe you could be so out of shape considering how much the townspeople chase you around with torches.”
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Cheech and Chong Roasted (2008)
Not many people know about this roast because it only aired on TBS, but it’s another great Giraldo set. It features my favorite roast joke of all time, his joke about Ralphie May watching porn. Tom Arnold also makes an appearance and remember the jokes he makes, because just a few years later Giraldo would get a shot at him again. The second time around Tom Arnold seemed just absolutely rattled. These may have been some of Giraldo’s best jokes about the people subjects of the roast.
Favorite Joke(s)
“Tom [Arnold], of course, he’s famous for marrying Roseanne, and that’s about it. Tommy Chong thought about replacing Cheech with Tom Arnold. They were going to call it Leach and Chong.”
“[Ralphie May] You’re the only guy who watches porn and cums when the guy delivers the pizza.” (Rest in peace, Ralphie May)
“Penn Jillette, with your greasy ponytail, you look like a male stripper who swallowed a male stripper.”
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The Comedy Central Roast of Larry the Cable Guy (2009)
In the Greg Giraldo documentary, his friends noted that he actually seemed to be cracking and letting a lot of truths out in his jokes about Larry the Cable Guy. This was the roast where he yells at Larry the Cable Guy, “How the fuck are you so popular!?” It lends to why I loved Giraldo so much, he always felt so real on stage. He also absolutely ethers Toby Keith in this roast.
Favorite Joke(s)
“Lisa Lampanelli, keep it going for that guy, wasn’t he funny? … I love the pink camouflage Lisa, you look like General Fatton. Holy shit, you fat fuck, who knew Lane Bryant had an army.”
“I’ve never roasted a fake character before. Maybe next year we can roast SpongeBob Squarepants.”
“Your fans can’t even afford cable. They’re not coming cause they think you’re funny, they’ve just never seen a cable guy. You could’ve come up with other characters your fans have never seen, like Larry the Dentist, or Larry the Librarian or Larry the High School Diploma.”
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The Comedy Central Roast of Joan Rivers (2009)
As someone who isn’t really a fan of Kathy Griffin, I loved Giraldo opening up by just laying into her. This was a weird mix of characters in terms of people on the dais and he managed, once again, to weave all of the jokes together perfectly. The Roast of Joan Rivers wasn’t all that great as a whole, but Giraldo’s set made it memorable. Also, this was the second time that he really made Tom Arnold uncomfortable. Try and spot the random Chris Pratt and Anna Farris cameo.
Favorite Joke(s)
“Kathy [Griffin], you look like Ronald McDonald fucked Lucille Ball’s corpse and pushed it down a flight of stairs.”
“What a night, a couple of trolls, a fairy and a giant all going after a sunken-eyed little monster who is obsessed with jewelry. It’s like ‘The Lord of the Rings’.”
“Brad Garrett, from ‘Everybody Loves Raymond’. You are a fucking monster Brad, how did you ever get your head so far up Ray Romano’s head with those bolts in your neck.”
“[Gilbert Gottfried] You look like you smell like pee.”
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The Comedy Central Roast of David Hasslehoff (2010)
This was, unfortunately, Greg Giraldo’s last roast before passing away about a month later. He was on his game as always and it was nice to see him have some older roast subjects on the dais for him to knock down one-by-one yet again. It’s still wildly upsetting that this was his last roast.
Favorite Joke(s)
“How fat do you [Jeff Ross] plan on getting? You’re fattening up more than you’re aging. You’re like the Curious Case of Benjamin Glutton.”
“Of course it wouldn’t be a roast without Pizza Lampanelli. Good to see you Lisa, I’ve never seen a circus bear in a pantsuit before. Lisa seems very confident, but she’s actually not, she’s very sweet. She was telling me backstage she had knots in all four of her stomachs.”
“[Hulk Hogan] Keep your shirt on bitch tits. You’re 80. You had a reality show called ‘Hogan Knows Best’, it should’ve been called ‘Hogan Grows Breasts’.”
“Hasslehoff, have you ever not been drunk? You used to have a car that would start when you talked to it, now you have a car that won’t start when you blow into it.”
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So there you go, I hope these stay up for a long time because people deserve to see the genius that was Greg Giraldo. The fact they are so hard to find is just ridiculous. What was your favorite joke from Greg Giraldo’s sets?
BONUS: Here is Jimmy Kimmel’s set from the Roast of Flavor Flav. Him going back and forth with the ‘Flavor of Love’ girls was fantastic.