There is perhaps no task more difficult for an entertainer than serving on the dais of some poor-but-lovable celebrity’s roast. Sure, it already takes serious guts for a comic to stand in front of a packed house and make everyone laugh a la truTV’s new Comedy Knockout, but when your job is to insult everything about a person, from their looks to their résumé, and make them and an even bigger audience laugh in the process, well, you better damn well bring your best game. There’s a fine line between being hilariously mean and bombing to the collective gasp of a crowd, and only a handful of comics have ever been able to truly dominate the art of the roast.
What’s unfortunate for roast aficionados, though, is that we don’t even get to see some of the best insults, jokes, and routines each year, because the biggest events are often private. And while we most often associate the art of the roast with the events that are televised, the best and often most brutal jabs come from behind closed doors, or even at the events that happened decades before we were born. That said, let’s take some time to acknowledge, honor, and rank some of the most hilarious roast takedowns we’ve ever heard.