8 Highly Descriptive Burns

8 Patrice O’Neal on Seth MacFarlane

“I got a critique about Seth. It’s too much Seth. It’s almost like he’s jealous of his own creation, where he wants to prove ‘I’m better than the cartoons.’ But he’s not better than the cartoons.”

From his legendary shortly pre-mortem performance on the Roast of Charlie Sheen, O’Neal took on host Seth MacFarlane. Ignoring any of the easy insults about MacFarlane’s show or elfin appearance, O’Neal instead launched into something that sounds like the notes of an annoyed therapist. It might feel mean to make fun of somebody’s looks, but it’s a less crushing option than someone making fun of the core of your being and deepest insecurities.

7 Dana Gould on Bob Hope

“If you’ve ever held a tube sock full of dead goldfish, you know exactly what Bob Hope’s arm felt like. … His eyes didn’t look like eyes, they looked like soup, with eyes in it.”

Bob Hope was a comedy icon, and at the time Dana Gould recorded the album this track is from, dead — two things that usually keep people from lighting into someone with furious abandon. Unluckily for Hope, and luckily for the rest of us, Hope had been such a notable and colossal asshole to Gould during a commercial taping that he felt perfectly comfortable verbally pissing on his grave. You don’t want people to insult your memory, and doubly don’t want them to do it in poetic fashion, to applause.

6 H.L. Mencken on FDR

“If Franklin Delano Roosevelt became convinced tomorrow that coming out for cannibalism would get him the votes he needs so sorely, he would begin fattening a missionary in the White House yard come Wednesday.”

Again, if you’re a public figure, I cannot recommend enough against making an enemy with a talent for the written word. It causes a high probability that their shit-talking of you might be timeless enough to circle your grave for decades afterwards. Franklin Delano Roosevelt made just such an enemy in author H.L. Mencken, who penned this vivid criticism of his politicking. FDR may have gotten the last laugh though, as he’s still remembered fondly by history, while Mencken’s diary exposed him as an anti-Semite, racist and Nazi sympathizer.

5 Joan Rivers on Bo Derek

“Bo Derek turned down the role of Helen Keller because she couldn’t remember the lines.”

Joan Rivers was one of the most quintessential insult comics for a generation, with a talent for the backhand that would rival most tennis pros. Understandably, she was a constant font of laser-focused verbal jabs, which makes it hard to choose just one. I settled on her targeting of bead-haired sex symbol Bo Derek, in whom Rivers found a reliable target for general bimbocity. In the end, Derek herself had to respect it, sharing her favorite of Rivers’ insults after her death on Twitter: “Sign said wet floor — so she did.”

4 Greg Giraldo on Joan Rivers

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“How much worse could your real face look than that clown mask you had welded onto your head? You used to look your age, now you don’t even look your species.”

If you’re going to be an insult icon, you have to be able to take as good as you give, and Rivers was a phenomenal sport. When she had her own roast, it was an honor to anyone invited, and a warning to bring their A-game. Greg Giraldo knocked it out of the park as to be expected, since he seemed like an heir apparent of Rivers before his untimely death. He took on Rivers’ heavily modified appearance, a common target, but with enough creativity to make it stick.

3 Jon Stewart on Rush Limbaugh

“Rush — the quivering rage heap who is apparently desperately trying to extinguish any remaining molecule of humanity that might still reside in the Chernobyl-esque superfund cleanup site that was his soul.”

We’ve cycled through so many Stewart Lites in the aftermath of his time on The Daily Show that it can be tough to remember just how much of a cultural touchstone he was. Unlike his successors, that viewership and devotion were well-earned. He was never better than when he was filled with genuine, vitriolic, verbose rage toward someone entirely deserving. Watching him tear into Rush Limbaugh was pure catharsis, like watching someone smash a street preacher’s megaphone.

2 Nikki Glaser on Rob Lowe

“You look like you’re sculpted. I mean, you put the ‘statue’ in ‘statutory rape.’ … God, I had such a crush on you when I was a little girl. If only I’d known that’s when I had my best shot.”

Like peanut butter around a poison pill, Glaser, a roast fixture at this point, butters Rob Lowe up complimenting his appearance before reaching directly into his darkest memories and unearthing a widely forgotten one in devastating fashion. Reminding everyone of his sex tape with, unknowingly, a minor, but doing it in a masterful fashion is just a deep burn, perfectly balanced in so many facets. There’s a reason she has continued access to the roast dais.

1 Bill Burr on Philadelphia

Impossible to quote just one section, who can forget an enraged (well, slightly more than usual) Bill Burr’s screed against the entire city and spirit of Philadelphia? He takes to the City of Brotherly Love with all the goodwill of a nuclear bomb and levels it. Even better is knowing the whole thing was completely unplanned, meaning that this fury was truly, deeply heartfelt.