That said, the key to a successful roast is a subject willing to take personal abuse while laughing about it, says Barry Dougherty, editor of the Friars Epistle newsletter and author of The Friars Club Bible of Jokes, Pokes, Roasts and Toasts. For example, when the Friars planned to roast Kelsey Grammer in 1996, the Frasier star unintentionally provided extra material. "What made him such a good target is we had scheduled to roast him at a certain day, and then he flipped his Dodge Viper over and ended up in the Betty Ford Clinic," Dougherty says. The Friars still roasted Grammer, and emcee David Hyde Pierce referenced his co-star’s addictions right from the start, joking "Hi, my name is Kelsey Grammer and I’m an alcoholic" before claiming their cue cards were switched.

While Grammer had the wherewithal to laugh at his personal problems, not everybody will. "If you know a person well enough that you’re doing a roast, you should know them well enough to know what they’re most sensitive about," Caroselli says. "It’s one thing to joke about their drinking if they joke about it themselves. It’s okay to make fun of Dean Martin’s drinking—it’s not okay to make fun of Judy Garland’s drinking."

Know your target before taking aim, says Barb North, a Woodland Hills, Calif., comic who writes and performs roasts. "Some sort of relationship with the person is really, really valuable," says North, who runs Brook Forest Entertainment, LLC with her husband, Steve. "When you’re writing material, you don’t want to rip them to shreds, but find a vulnerable area that’s also a fun vulnerable area for them." She also cites the value of picking on people who can afford to be laughed at. "The kids can make fun of the teachers, the teachers can make fun of the administrators, the administrators can make fun of the school board," she says. "The higher the position the person being made fun of is, the more comfortable people will feel laughing."

North says good material can come from thinking about what roastees say about themselves, their minor annoying habits, what about them is lovable and areas where they could improve. Bill Butler, a San Diego-based writer who has penned roasts for hire since 1988, says jokes can be made at anyone’s expense. "It works both ways. If some guy is fat and cheap and loud and the whole bit, then you’ve got a ton of material there," Butler says. "If they’re total saints, then you can make up all types of great stuff about them. You pick on the obvious—and if they don’t have obvious weaknesses, pick on their obvious strengths."