Getting up in front of an audience and telling jokes is terrifying, and it takes a very specific type of lunatic to decide that they’d like to make a career out of it. Regardless of whether a comedian is any good, they can’t be accused of being timid.
Below are the five ballsiest stand up routines of all time. Can you think of any others I’ve missed? Let me know in the comments.
5. “I ain’t scared of you mother fuckers” – Bernie Mac
I love this entire routine. I love the swagger. I watch it whenever life takes some swings at me and I need picking up. Sometimes life, and all it’s detractors need a reminder – I ain’t scared of you motherfuckers.
The story behind this one is that he was doing “Def Comedy Jam” and it was a huge “make-or-break-your-career” kind of night. If he did well on this national stage, it could boost his profile and take him to the next level.
Famously, the audience was hostile to the other comedians and were making their lives difficult. The comedian who went on before had been booed. Apparently Bill Bellamy was backstage with Bernie and told him to watch out. Bernie replied “I’ve been going at this too long and I’ve worked too hard. I ain’t scared of ’em”.
He went out hot, gave them hell, and won them over. The jokes aren’t that hot, but the swagger is astounding.
4. The Philadelphia Incident – Bill Burr
You know you need to buckle in when the actual set is known by the more colloquial name “The Philadelphia Incident”
This is the only recording I can find, the visual quality is crummy. This is a very similar story to the Bernie Mac one. Burr was on the road with The Traveling Virus Comedy Tour and he, and the rest of the comedians were in Philadelphia and the crowd was being brutal to the comedians. They were drunk, unruly and they booed every performer off the stage.
Bill Burr came out and rather than do his set, he went on a twelve minute improvised rant against the city of Philadelphia.
Every minute, he counts it down (Ten minutes left, nine minutes left, eight minutes left) and he… doesn’t really win over the audience. They keep booing and he keeps calling them stupid, racist motherfuckers.
Heads up – This is Bill Burr. The language is pretty rough in this one.
3. The Roast of Bob Saget – Norm MacDonald
I should probably just write an entire article on Norm MacDonald. He’s the funniest comedian alive and the best comedian of a generation. I think everything he’s done is brave, groundbreaking and gutsy. It’s really difficult to pick just one of his routines and call it the ballsiest, but I have to go with his roast of Bob Saget.
For anyone who hasn’t seen the show, they get B and C level celebrities and have their friends roast them. Norm MacDonald decided to use this opportunity to publicly bomb.
Rather than perform funny jokes, Norm decided to pull out the cheesiest, oldest, hoariest jokes he could find. Here’s a sample – “Suzie Estman of course, is famous for being a vegetarian. She may be a vegetarian, but she’s still full of baloney in my book!”
This continues for six minutes. At no point does the audience really laugh or even understand the meta joke he’s making (Bob Saget made his career on Full House, a show filled with terrible, punny humor).
The comedians love it. I can’t find this on YouTube, so here’s the version from streamable
Honorable Norm MacDonald mention – the ESPN Awards show which he closes with this joke:
“And there’s Charles Woodson, what a season he’s had. He became the first defensive player to win the Heisman trophy. Congratulations Charles, that is something that no one can ever take away from you. Unless you kill your wife and a waiter*. In that case, all bets are off.”
*For those a little younger, this is a reference to OJ Simpson, also a Heisman trophy winner.
Honorable mention 2 – the moth joke on Conan
Honorable mention 3 – The Courtney Thorn-Smith interview on Conan
Honorable mention 4 – his entire body of work on Weekend update
Honorable mention 5 – The President’s correspondence dinner.
Hey, speaking of the presidents correspondence dinner…
4. The President’s Correspondence Dinner – Stephen Colbert
I’ll let the youtube description do all the work on this one:
Stephen Colbert mocks President Bush to his face at the 2006 White House Correspondents’ Dinner.
Yep. That’s it. Stephen Colbert spent twenty minutes making fun of the sitting president to his face. And not in a “ha ha we’re all friends” sort of way. No, he tears into him for being ineffective, unpopular and stupid. He is ruthless. Bush is not impressed.
He also takes some wonderful shots at the media – “(on the quality of their reporting) Write that novel that’s been kicking around in your head. You know, the one about the intrepid, Washington reporter with the courage to stand up to the administration? You know, fiction.”
5. Andy Kaufman’s entire career, but my favorite, the Friday’s TV show incident.
Okay, so this technically isn’t a stand up routine, but it’s pretty great.
“Friday’s” was a show like SNL, and it was live. Andy thought it would be funny to interrupt the skit by faking that he wouldn’t do the lines. The only other person in on the gag is a very young, pre-Seinfeld Michael Richards. His co-stars aren’t amused and neither is anyone on the set and – on live TV – the whole skit degenerates into an actual fight.
The best part comes when, after muffing several lines, Michael Richards gets up, walks off stage and returns with cue cards that he throws on the table.
Gotta love Andy Kaufman. He was like teenage youtube celebrities before youtube existed, his whole career was one extended prank.