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The Ten Best Comedians of the 21st Century

In the six months we’ve been doing this blog, I’ve written my fair share of controversial articles. While I never go out of my way to be purposefully provocative, writing about things like race, politics and culture inevitably stir strong emotions in some people. However, I think this will be my most continuous article yet. I am going to make a definitive list of the best stand-up comedians of the 21st century (all 13 years of ’em) based solely on their stand-up work. Movies, TV shows and whatever else some might have done will not be factors, but might be mentioned.

#10 Mitch Hedberg

Mitch died way too young, but before he left us, he produced some of the best one liners of all time. One of my favorite things ever is watching his stand up and waiting for the 5-10 seconds for one of his jokes to actually sink in. His deadpan, stoner delivery often gave way to him cracking himself up, but when he could do it straight, all the ridiculous things he said seemed all the more insightful.


 I bought a $7 pen because I always lose pens and I got sick of not caring.

The depressing thing about tennis is that no matter how good I get, I’ll never be as good as a wall.

I haven’t slept for ten days because that would be too long.

My friend asked me if I wanted a frozen banana, I said “No, but I want a regular banana later, so… yeah.”

I went to a record store, they said they specialized in hard-to-find records — nothing was alphabetized.

#9 Donald Glover

Donald Glover aka “Troy from Community” aka Childish Gambino might be on this list a bit prematurely because he still doesn’t have a lot of stand-up material. However, what he does have is great and given his young age, it seems very likely he’ll have way more in the future. Also, he raps under the name Childish Gambino, check it out. The beats are good and he has some very clever lyrics.

“Armenian girls are the black girls of white girls.”

#8 Bill Maher

I’m going to guess he’s not for everyone, but since I love politics and liberals actually have a sense of humor and funny people, I enjoy jokes about politics. You have to be up on current events and especially election news to get some of his jokes, but he’s probably the cleverest person doing political stand up today. He’s able to make a lot sense and fantastic points, and can effortlessly destroy the other side’s arguments and expose their hypocrisy all while cracking people up. In terms of wit, the Right has no one who can compete.

#7 Sarah Silverman

Honestly, I’m not sure if I’m putting Sarah on the list because I think she’s funny or because I think she’s hot or because I felt like I needed to have at least one woman on here. Just joking, I know it’s because she’s hot. I love her. She’s so cute and has such a sweet innocent voice. All of which she exploits to say some of the most racist, crude and offensive stuff ever. It’s great.

“Different Religions”

#6 Bill Burr

You know a white guy is funny when he can go on BET (Black Entertainment Television) and kill it. I don’t know if it’s just the stand-up routines of his that I’ve seen, but this guy always seems to get into it with his audience, as well, which adds a lot to his Boston, angry, yelling man bits.

#5 Kevin Heart

Half the reason he’s so funny is because he’s so willing to make fun of himself. I think his humor is also impressive because he might use race the least of everyone on this list. I swear I’m not factoring this into his ranking, but you need to check out his show The Real Househusbands on Hollywood. It’s a fake reality show with Nick Cannon, Robin Thick, Nelly and tons of other cameos.

#4 Chris Rock

I’m not going to lie; he hasn’t done anything particularly good lately, and his most recent stand up, which was way back in 2008, “Kill the Messenger,” kind of sucked. However, his first few “Bring the Pain,” Big Ass Jokes,” “Bigger and Blacker,” and “Never Scared” remain some of the funniest comedy shows of all time.

#3 Katt Williams

As a single stand-up performance, The Pimp Chronicles pt 1 might be the most perfect 1 hour show ever done. Either that or I was really really high when I watched it….or both. The first time I watched it, I instantly put it on replay and watched it again. While the stuff that followed wasn’t quite as good, that has more to do with the fact that he set his own bar so high. But if the N-word makes you uncomfortable, you might want to skip Katt. If you love Michael Jackson, you will for sure what to skip this clip.

“Michael was trying to be a white woman his whole life…”

# 2 Louis CK

OK, I’m kind of late to catch on to Louis, and, since I don’t have kids, I’m sure some of the deeper brilliance of his humor about family life is lost on me. But still, there is no denying how funny he is and most of it is stuff that’s so obvious but that no one else has said before,  just take the stuff he says about race. So good.

# 1 Dave Chappelle

His stuff is funny, brilliantly insightful, full of social commentary on race relations and there’s a ton of it. Most comedians can only dream of having one hour of good stuff, but Dave has hours upon hours of material that is off the chart funny, highly quotable and very re-watchable. I think it might be all the voices he does while telling stories that makes him so endlessly entertaining for me. And this is all without even going into his brief run on TV with the Chappelle Show.

“Chip, NO!”


Side Bar: While my list is objectively perfect, I am open to ridiculous suggestions about who should actually be on it. Try to add a Youtube clip/link if you can. Personally, the only person I was on the fence about was Dane Cook.

Brian M. Williams
Brian is the author of the recently published travel memoir "Stranger in a Stranger Land: My Six Years in Korea." (Click this profile for more information.) He's also a law school grad with Southern charm and Virginia roots. He recently returned to America after nearly seven years traveling and working abroad. He loves dive bars, international travel and foreign accents. He's particularly good at small talk and was the first person to notice there's no "I" in "team."

12 thoughts on “The Ten Best Comedians of the 21st Century

  1. Donald Glover??? GET OUTTA HERE. Your Community fanboy is showing! This list makes me sick! But comedy is subjective. There are terrible comedians who sell out everywhere they go….so I guess that means somebody thinks they’re funny.

  2. With the exceptions of Chapelle and CK (Heberg too) I must concur with Mr. Wiberg. I’m disappointed there’s no Maria Bamford or Patton Oswalt. I can understand a lot of my favorites not appearing on this list…ya know, cuz it’s not my list, but I am baffled to see Maher and no Bamford.

  3. Have you ever seen Steven Lynch? We seem to have the same taste in comedy, so I think you’d really appreciate his talent. I hope you check him out if you don’t know him already. And if you do know him, how could you not include him on this list??!! 🙂

  4. this list is ridiculous! Are you okay??? No Richard Pryor??? C’mon, man! Ever heard of Bill Cosby??? Robin Williams??? George Carlin??? HELLO???

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