Top 20 Stand-Up Comedy Specials from the 2010s If you need a laugh, these comedians deliver

The 2010s were a great time for comedy fans. Podcasts, YouTube, and streaming services gave stand-up new avenues to make fans, and innovative comedians pushed the boundaries to release specials everywhere they could.

Here are the funniest stand up comedy specials from the past decade, as we prepare for the 2020s.

20. DeRay Davis: Power Play (2011)

DeRay Power Play

DeRay Davis brings the laughs in an energetic debut to the televised comedy special. He comes off as a young Eddie Murphy, with razor sharp observations of blue-collar life. Filmed at the beginning of the decade, it’s still relevant (and hilarious) today.

19. Joan Rivers: Don’t Start With Me (2013)

Joan Rivers Dont Start With Me

Joan Rivers was nearing the end of her career (and life) when this special was filmed. It’s not her best work, but it shows the biting cynicism that made her a legend.

18. Patton Oswalt: Annihilation (2017)

Patton Oswalt

Patton Oswald specializes in surrealist humor. I’ve seen him live at The Improv in his heyday, and he’s brilliant. Now much more mature, Oswalt takes on the death of his wife and some seriously profound subjects with ease.

17. Maria Bamford: The Special Special Special! (2012)

Maria Bamford Special

Maria Bamford always takes comedy to the next level, and this special is no different. She curtails the norms of the genre to perform an awkward stand-up special to an audience of just her parents. And it gets dark fast.

16. Doug Stanhope: Before Turning the Gun on Himself (2012)

Doug Stanhope Before Turning the Gun on Himself

Doug Stanhope struggled to find relevance for what seems like his entire career. His rants are legendary, but it also keeps him from being accepted by the mainstream. This is his last great stand-up special so far, but so long as he’s alive, this modern-day Lenny Bruce has a chance to come out punching. I’m always rooting for a Bisbee resident in this world.

15. Wanda Sykes: Not Normal (2019)

Wanda Sykes Not Normal

Wanda Sykes pulls no punches, and she has the power these days to do and say pretty much whatever she wants. And her target in this special is Donald Trump and the strange state of the political climate moving into the 2020s.

14. Jimmy Carr: Funny Business (2016)

Jimmy Carr Funny Business

Jimmy Carr will make a joke about anything, and his British accent makes him more endearing than Stanhope. He’s mechanical in his delivery, but it just works (so long as you can stand his laugh).

13. Michael Che Matters (2016)

Michael Che Matters

Michael Che spends his weekends slinging jokes on SNL‘s Weekend Update, and this special brings his personality and humor to the stage. He addresses all the same newsworthy issues as he does on SNL, while also getting into more personal matters.

12. John Mulaney: The Comeback Kid (2015)

John Mulaney The Comeback Kid

John Mulaney is more of a storyteller than comedian. Watching this comeback from a failed TV series proves he’s one of the most professional comedians in the game too. He has a comfortable guy-next-door vibe similar to Pete Holmes, but he comes off as someone you actually admire.

11. Anthony Jeselnik: Thoughts & Prayers (2015)

Anthony Jeselnik Thoughts and Prayers

Anthony Jeselnik is an insult comic who digs into dark places, similar to Jimmy Carr. He’s happy to keep pushing as deep as possible into offensiveness. And even though you know what’s coming, he still manages to hit you with a few unexpected punchlines.

10. Ryan Hamilton: Happy Face (2017)

Ryan Hamilton Happy Face

Not only does Ryan Hamilton look like a creepy cartoon character, but he’s aware of it. He’s a clean comedian but that doesn’t take away from his humor. He maintains an edge and stage presence throughout this special exploring his Idaho roots and trying to survive in the New York scene (or New Yorkers trying to “make it” in rural Idaho).

9. Jen Kirkman: I’m Gonna Die Alone (And I Feel Fine) (2016)

Jen Kirkman

Jen Kirkman is a conversational comic who touches on a lot of topics of aging as a woman. She rides a line between Ellen DeGeneres’s self-conscious observations and Patton Oswald’s profound statements of life. Kirkman really grew as a comedian over the years, and if you’re not aware, she wrote most of Mrs. Maisel’s jokes for Amazon.

8. Dave Chappelle: Equanimity (2017)

Dave Chappelle Equamanity

Dave Chappelle is a master stand-up comic, and another I’ve seen perform live in his heyday at The Improv. He dropped a two-part stand-up special on NYE 2018 on Netflix, and it proved he still has that laid-back cool that made him famous in the first place (although not as famous as Kevin Hart to his son).

7. Jim Jefferies: Fully Functional (2012)

Jim Jefferies

Jim Jefferies is an Australian comedian willing to tackle the problems of everyday life, from fatherhood to visiting the emergency room. But he’s also not afraid to talk politics, religion, and even terrorism. This special reminds me of why he got hired on with Comedy Central in the first place.

6. Louis C.K.: Hilarious (2010)

Louis CK Hilarious

Before he became a casualty of the #MeToo movement, Louis C.K. was the biggest comedy star around. Hilarious was the first stand-up film ever accepted into the Sundance Film Festival, and this concert film shows him at his best. He discusses his faults in parenting, marriage, being a man, and everything in between. Anyone who actually watched his shows knows he was always honest and transparent.

5. Mike Birbiglia: My Girlfriend’s Boyfriend (2013)

Mike Birbiglia My Girlfriends Boyfriend

Mike Birbiglia is another storyteller comedian, but he’s just so good at it. As he describes meeting his girlfriend and the evolution of their relationship, you wonder if you’re even watching a stage performance or just a friend talking at a party. His special brand of self-deprecating humor really shines in this 2013 special.

4. Kevin Hart: Laugh at My Pain (2011)

Kevin Hart

Only time will tell how Kevin Hart enters the 2020s after his major car accident, but he entered the 2010s on top of the world. This hybrid special was filmed over two days at the end of a 90-city tour, and he tackles divorce, drug addiction, death, and more with a sense of humor that made him one of the shining comedic stars of the decade.

3. Tig Notaro: Happy To Be Here (2018)

Tig Notaro Happy to Be Here

It’s interesting that Tig Notaro helped take down Louis C.K. after he pushed so hard for her to have a career. He’s not wrong – Notaro is one of the best comedians in the game, and this special shows it. She very much looks, acts, and sounds like a Portlandia character, but she takes chances few comics do. And she throws a surprise Indigo Girls performance in as icing on the cake.

2. Bill Burr: I’m Sorry You Feel That Way (2014)

Bill Burr Sorry You Feel That Way

Bill Burr has a brutish Bostonian accent and blue-collar perspective on life that consistently brings the laughs. He was podcasting before Maron and Rogan, and his stand-up specials are all seriously classic. This black-and-white film is one of my personal favorites from him though. Burr is unapologetic and goes right at the crowd anytime they get silent on a topic like domestic abuse. This is a rare comedic performance and instant classic.

1. Neal Brennan: 3 Mics (2017)

Neal Brennan - 3 Mics (2017)
Neal Brennan – 3 Mics (2017)

Neal Brennan started out writing with Dave Chappelle, and co-wrote and co-created much of his best work. Now he’s pushing the boundaries of stand-up himself, and he deconstructs both his career and the art of comedy in this special. Brennan has three mics on stage, one is for one-liners, two is for stark insights into his depression, life, and career, and three is for traditional stand-up. As the special ends, you wonder whether anybody will ever be able to top the genius of what Brennan has done in this special, much less his comedic career.


Dr. Brian Penny is a former Business Analyst and Operations Manager at Bank of America turned whistleblower, troll, and freelance writer. You can find his work in Cracked, High Times, HuffPost, Lifewire, Forbes, Fast Company, and dozens of other places, although much of it is no longer under his name. Dr. Penny loves annoying fake media.

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