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Burned: The Oral F***ing History of the Comedy Central Roast

But with Anderson, and subsequent roastees like William Shatner, producers would learn just how far was too far.

Lisa Lampanelli: During the Pam Anderson roast, some comic went on a tirade about Pam’s vagina, and it was just not funny. There’s nothing funnier than a good vag joke, but it went on way too long and every joke was lousy. She honestly looked like she was going to tear up, and I was so angry. I saw her look at Tommy Lee, and he mouthed to her, “Are you OK?” 
Anthony Jeselnik: With Shatner, his wife had drowned, so of course I wouldn’t fucking bring that up. When Mike Tyson was on—don’t make fun of Mike’s kid who died on a treadmill. Of fucking course not. As mean as I am with these things, I never make fun of a dead kid or a dead relative.
William Shatner (roastee): [Being roasted] sounds like great fun, and ultimately it is, but unless you’re set mentally and emotionally, it could have a nightmarish quality to it. It could be like a bad dream where people are poking fun at you in public. It’s not different from being in a torrid love affair—just let yourself go…
Jeff Ross: At the Shatner roast, I had some jokes about Farrah Fawcett, how I was in love with her as a kid and how I had her poster and would fantasize to her, and then I said, “But now you look like…” whatever—jokes about her being old and ugly. I get there, and she’s old, but she looked fantastic! The 12-year-old in me came out, and I got shy and said, “I’m not calling her an old beast and an old hag. She’s gorgeous! I still want to fuck her.”
As with the Pam Anderson roast before it, the Flavor Flav roast in 2007 posed a challenge to make sure that the dais presented a good balance, both racially and sexually.  
Doug Herzog: I’m always personally very conscious when we have women—it can’t be a dais full of guys. That just feels bad. Keeping a balance is important.
Jeff Ross: The Flav roast was coming off the year of the terrible Michael Richards thing, where he kept yelling the N-word in a comedy club. Racial humor was really under a microscope.
Joel Gallen: Flavor Flav’s comedic timing was so hyper at that point, and he was so nervous, that even though we worked with him on the best way to deliver a joke, I remember him laughing almost before he’d deliver the punch line. We had to work some pretty major surgery in editing.  
Flavor Flav (roastee): It was only later that I realized I came from this world. I was born and raised “playing the dozens,” and honestly, my first time having a roast, I didn’t actually know what it consisted of. If I’d known it consisted of me being able to tell my own jokes and do my thing and just play the dozens? Oh, man, I would have creamed those guys. I wanna do a part two. I wanna call it Flav’s Revenge.
For the next roast, honoring Bob Saget, producers filled the stage with heavy-hitting comics like Norm Macdonald, Gottfried, Greg Giraldo, Ross, Jim Norton, Susie Essman, Jon Lovitz, Sarah Silverman, Lewis Black, and the king of the insult comics, Don Rickles.  
Bob Saget (roastee): I was pensive at first, wondering what factor they were going to rip apart the most. They always go after your career—or whatever lascivious behavior you’re known for. But in this case I was concerned about people I’ve worked with. Especially the young people.
While there was no shortage of Olsen twins jokes, the highlight of Saget’s roast was when pal Norm Macdonald returned, briefly, to the corny, prime-time-safe humor of a more innocent age: “You’ll never be over the hill, not in the car you drive.” “She may be a vegetarian, but she’s still full of baloney in my book.” Not everyone grasped the concept. Those who did were in tears. 
Bob Saget: He made a creative choice. I talked to him the week before. I said, “Norm, what do you want to do?” and he said, “Aw, I can’t make fun of my buddy. I’m just gonna tell old jokes. Really bad old jokes. Jokes from, like, 200 years ago.”
Jon Lovitz (roaster): He was just doing it to be different from everybody else. “They’re being as dirty as they can? I’ll tell the corniest jokes possible!”