RANKED! Our 20 Favorite Stand-Up Comedy Specials of the Last 20 Years

The stand-up comedy scene has been flourishing over the past few years due to an influx of talent and streaming services like Netflix and Amazon. If you peruse Netflix’s lineup as often as we do, it feels like there’s a shiny, bright-eyed comedian launching a comedy special every other week. Similar to scripted television, it feels like the platinum age of stand-up comedy is upon us. A tidal wave of laugh-out-loud moments is available 24/7. Now seemed like an ideal time to throw together a ranking of the best comedy specials over the past 20 years. Enjoy!

Cover Photo: Netflix

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Best Stand Up Comedy Last 20 Years

20. Aziz Ansari, 'Buried Alive'

Parks & Rec star Aziz Ansari cracks the list here at No. 20. If you can handle his nasal-toned voice and unpredictable volume levels, you'll see that he's a product of comedy legends. Ansari is a terrific storyteller with an innate ability to paint a joke into form with only a few brushstrokes.
19. Hasan Minhaj, 'Homecoming King'

If you haven't heard of Hasan Minhaj, then Google him immediately. He's more of a story artist than a joke-teller, taking you deep into the darkness at times, but always leading you to the light with a witty punchline.
18. Anthony Jeselnik, 'Thoughts and Prayers'

So, you say you like dry, sarcastic, filthy, and mostly inappropriate humor? Then Anthony Jeselnik is your guy. He was named Comedy Central's Breakout Comedian of the Year in 2009 and probably hasn't enjoyed a second of it since, although you'd never be able to tell from his dead-pan delivery of hilarious material. A quick taste of the goods: “Yesterday, I accidentally hit a little kid with my car. It wasn’t serious. Nobody saw me.”
17. Sarah Silverman, 'We Are All Miracles'

The quick-tongued Sarah Silverman performed in front of an intimate audience of just 39 fans at L.A.'s speak-easy nightclub, Largo. Silverman pulls no punches with her jokes, but she does everything with a smile, so it almost feels good when you're being berated. Literally no topic is off the table for her: cellphone porn, crazy religions, specialty deodorants, terrible roommates, eyebrow waxing, her 19-year-old dog, and the miracle of existence. You'll love every second of the show.
16. Jim Gaffigan, 'Beyond the Pale'

Gaffigan's bit about Hot Pockets is what put him on the map. But that's just the tip of the iceberg. Gaffigan is respected by the entire comedy world. He's able to flawlessly deliver joke after joke with most mainstream audiences, while still being known as a comic's comic. Beyond the Pale is an example of a master craftsman at work.
15. Hannibal Buress, 'Comedy Camisado'

If there's an award for most stoned-looking comedian, it's forever going to Buress. His monotone delivery and general appearance makes you think you're stoned. But his comedy is chock full of culture-changing ideas and concepts, with a twist of annoyances he has towards random everyday life or people that piss him off.
14. Bill Burr, 'Let It Go'

Let It Go is the perfect cocktail of a Bill Burr performance, with tons of energy and stage presence, plus an insanely wide range of subjects: Oprah, self-checkout lines, male insecurity, government conspiracies, and self-important people that claim they “rescue” dogs....everything worth complaining about.
13. Patton Oswalt, 'Annihilation'

After an incredible tragedy in his personal life (his wife's death), Patton Oswalt fearlessly took to the stage for this emotional, honest, and hilarious Netflix special. And he didn't dance around the subject; in fact, most of the show's jokes are somehow centered around his personal life, his daughter, and his wife. He finds just the right amount of hilarity in the tragedy, and life's awkward daily routine after losing his wife. He tackles everything from having to inform his daughter of her mother's death to taking his daughter back to school and being berated by young kids' questions about his wife's passing. In a perfect way, it's absolutely beautiful how Oswalt dances through the tall field of melancholy with a sarcastic, relatable grin and quick-witted punchlines.
12. Ali Wong, 'Baby Cobra'

In Baby Cobra, Ali Wong poses a perfect commentary about transitioning from young adulthood to adulthood, single life to marriage, and marriage to motherhood, all while being super pregnant! Breaking the fourth wall of prenatal comedy, Wong became the first woman to ever perform a special while noticeably pregnant, bringing a hilarious juxtaposition to tons of her dirtier material.
11. Steven Wright, 'When Leaves Blow Away'

Steven Wright is an absolute comedy legend. He may have not invented monotone one-liners in the comedy hemisphere, but he damn sure perfected them. Here's a perfect example: "I got a new dog. He’s a paranoid retriever. He brings back everything because he’s not sure what I threw him."
10. Louis C.K., 'Shameless'

So, yeah, he's had a rough couple years offstage and off-screen -- all completely by his own doing. There's no defense for any of the depraved acts committed by Louis C.K. Having said that, back in 2007 he was a comedy golden goose and Shameless was a huge reason why. He became an icon very quickly, a comic's comic that somehow was able to appeal to mass audiences as well. With a sly grin, he touched (zing!) on everything from the pros and cons of weight gain, to taking bumper stickers way too personally, to deceiving your spouse and the aftermath that ensues. Too bad he ultimately went to the dark side.

Related: Louis C.K. Doesn't Need A Comeback; He Needs A Giant Life Pivot
9. Tig Notaro, 'Happy to Be Here'

Tig Notaro is another true master of deadpan, sarcastic rhetoric. She's perfectly self-deprecating and pretty much hates everyone, except her wife and two kids. Seemingly, years of therapy (both legitimate and onstage) have finally kicked in and she's the happiest she's ever been, but hasn't lost her edge in any way.
8. Mike Birbiglia, 'My Girlfriend's Boyfriend'

If you're not aware of Mike Birbiglia's incredible storytelling ability, we highly recommend getting on Netflix immediately. Watching him do his thing onstage is like having a conversation with your mildly dorky, but hysterically honest, cousin. Jokes fall from a city skyline of plotlines and real life situations when Mike is on the mic.
7. Mitch Hedberg, 'Comedy Central Half-Hour'

Mitch Hedberg is possibly the ultimate comic's comic. He was a lightning bolt of one-liners and silliness, like Rodney Dangerfield 2.0, disguised as a '90s hipster rocker. Hedberg was the king of finding the sarcasm in any situation: "When I pass a guy on the sidewalk handing out fliers, I always think he’s telling me, 'Here, you throw this out.'"
6. Tom Segura, 'Mostly Stories'

Tom Segura is the kind of dude you'd want to hang out with. He sucks you in with a regular-guy likability, and he has the hysterical skill of pairing spot-on different voices and dialects when he's quoting or describing characters in his jokes. It's absolutely brilliant and only mildly offensive.
5. Jim Jefferies, 'Bare'

Jim Jefferies has no filter and absolutely does not care what you think about it. He's kicked fans out of his shows for disagreeing with his views on religion, guns, war, the American government, and whether or not to vaccinate your kid. He set a record for the use of a certain four letter word that starts with "C" in a comedy special. Jefferies is quite simply the best thing to come out of Australia since Crocodile Dundee.
4. Chris Rock, 'Bigger and Blacker'

Chris Rock is a legend in the comedy hall of fame. He waxes political about every topic imaginable: racial profiling, police brutality, gun control, President Clinton, homophobia, racism, black leaders, and relationships. There's truly something here to offend everyone, but you'll also laugh your ass off.
3. Zach Galifianakis, 'Live at the Purple Onion'

Fat Jesus initially made a name for himself with his stand-up comedy life documented in Live at the Purple Onion. He brilliantly splices scenes together, mocumentary style, showing his time on the road, the stage, and also introducing the world to his twin brother, Seth (who he plays as well). To quote the unique comic: "When you look the way I do, it's hard to get a table for one at Chucky Cheese." Galifianakis is a unique gem of a comedian, playing off uncomfortable silences, sarcastic undertones, and sly jabs at just about everyone and anything.
2. Dave Chappelle, 'Killin' Them Softly'

Way before Chappelle's Show, Dave Chappelle was killin' crowds with his incredible joke-telling and joke-writing ability. Killin' Them Softly is a damn near perfect example of well-crafted jokes disguised as true stories with a nonstop waterfall of punchlines. Chappelle is absolutely masterful and owns the room, even making himself laugh several times, giving him an image of relatability as well.
1. John Mulaney, 'New In Town'

John Mulaney may be the most self-aware comic you'll ever see onstage. He plays off his squeaky-clean appearance while dropping nuggets of self-deprecating humor in a fresh, appropriately inappropriate kind of dance that we've never seen before. It works perfectly. You believe everything he says as truth, especially his personal stories about his family, his parents, his drinking problem, teen angst, and relationship struggles. "I think I was supposed to be gay. I think, like in heaven they built 3/4 of a gay person and then they forgot to flip the final switch, and just sent me out."