The Ten Best Comedy Specials of 2016! Vote for Your Favorite

Our celebration of all things comedy in 2016 continues with the 10 best comedy specials released this year. This was our most difficult category, because there were more than ten specials that were outstanding. Enjoy our picks for funniest, most original comedy specials this year.

In 2014, you picked Jim Jefferies “Bare” as the comedy special of the year. In 2015, the honor of best special went to Jim Norton’s “Contextually Inadequate.” This year, Jefferies is back with a new special, Freedumb, and he’s taking on nine other outstanding hours from Big Jay Oakerson, Tom Segura, Bert Kreischer, Ali Wong, Doug Stanhope, Barry Crimmins, Gary Gulman and Colin Quinn.

We only included hour specials, but we have to give honorable mention to Joe Machi for a half hour special that was truly special. So many great hours we didn’t have room to include in the top ten, but were exceptional and would have easily landed on a top ten list in any other year. See as many as you can- there is greatness to be found all over 2016.




Big Jay Oakerson had it all for his long-awaited hour special, he had a live tear-the-roof-off band bring him out on stage and the stage was set for a comedy special for a true comedy rock star. There was fire, there were banners hanging from the rafters, and even the venue was chosen carefully- Webster Hall is a major concert venue. Big Jay took the stage like he owned the place and then sat down quietly on a simple stool and spent an hour absolutely owning the theater, the audience, and the hour. And it was a filthy, dirty, hilarious hour. Big Jay’s big hour special debut was a long time coming, and worth the wait. Earlier this year, we declared Big Jay Oakerson the next comedy rock star, and he came through with all that and more.


When Michael Che isn’t at 30 Rock working on Saturday Night Live, he is out doing sets all around New York City and the country. If you only know Che from SNL, you are missing more than half the story. Che’s stand up is sharp, it’s young, it’s unique, and it’s hilarious. Che’s joke writing is on point, and full of surprises and his laid back I-don’t-give-a-fuck delivery is completely disarming. Add in that he’s also great at working the crowd- a skill he weaves throughout his special expertly. Che hits on some major hot button issues, and you may have heard others take on those topics, but never quite like Che. He is going to be a major player in years to come.


Ali Wong turned into an overnight sensation many years in the making with her special Baby Cobra where she took on everything from the perks of being a housewife to using the bathroom at the office. She is bold, fills the room with her presence and has attitude that young girls will emulate for years to come. Even though she was seven months pregnant when she taped the special- and the feat itself is pretty impressive- that’s not why Baby Cobra made our list. The hour is damn near flawless, expertly constructed, with not a single syllable wasted, not a breath out of place, and yet so well delivered that it never felt rehearsed. The topics are diverse, original, and hilarious, and we love Wong’s point of view. An instant classic.


Awaiting a special from Colin Quinn is like waiting for presents on Christmas morning except better because you usually learn something. Even if you’re not from New York, you will still absolutely love this lesson in how the personalities who live in New York City have evolved through Quinn’s lifetime. Based on his 2015 best-selling book, “The Coloring Book”, The New York Story is nostalgic in the very best way, and even if the times he talks about are before your time, anyone can relate. It’s brilliant in style, delivery, tone, and of course content. Colin smashes right through political correctness taking on stereotypes and ethnic groups, but without offending or demeaning a single group because there is no hate, there is no superiority, there is no condescension anywhere to be found. Absolutely must watch..


Bert Kreischer is an American original. Who else would take off their shirt the moment they hit the stage? Kreischer’s personality and his comedy are pure joy. He laughs as much as the audience does- and that’s a lot. His energy is contagious and his storytelling is among the best of the best. And of course, his stories are already the stuff of legend. His epic college years have given way to fascinating tales of fatherhood. But this special will be most remembered for the complete telling of the story of how Bert got the nickname “The Machine.” Legendary.


Just 2 years ago a Netflix special took Tom Segura to new heights. He went from being a tremendous talent that other comedians know to one of the great headliners. His new special was anticipated as a highlight of 2016, and he did not disappoint. Like his buddy Bert Kreischer, Segura is a master storyteller, and in Mostly Stories, he shares one of his best– a story about meeting Mike Tyson that is one of the best stories we’ve ever heard. “Where’s your show?”


2016 is the year that NBC’s Seeso streaming platform proved they can compete with the best networks for outstanding comedy specials. There are some strong gets and our pick for the best of the Seeso specials is also one of the strongest on any platform– Doug Stanhope’s “No Place Like Home” which was executive produced by his buddy Johnny Depp. Who else but Stanhope can make a special that covers topics like guns, the holocaust and assisted suicide so entertaining? Stanhope is a comedy powerhouse, completely original and unimitatable. Stanhope is more than a comedian, he is a way of life, and No Place Like Home is one of the best of the year.


Gary Gulman is a comedy maestro.  The special is truly an example of near-perfect joke writing. It’s the kind of special that prompts other comedians to drop their jaw in awe and reverence and declare, damn, that’s brilliant. The primary structure of the hour is so well honed, and then on top of perfection, Gulman throws in little quips that make something already hilarious even funnier.  Gulman’s use of the language is masterful, and beautiful to watch, or listen to. One of the best touring comics in America today, you cannot miss Gary Gulman: It’s About Time.


Boston comedy scene legend Barry Crimmins released his first ever special and it’s easily one of 2016’s strongest comedic performances, Whatever Threatens You. The special, shot in Lawrence, Kansas, was directed and produced by Louis CK, who described Barry as “a comedian who cares about what he is saying and who brings integrity and experience and an unmatched skill as a writer to his performance,” and we couldn’t agree more. Whatever Threatens You is political satire and comedic activism at its finest in a time when we need it most.


In 2016, Jim Jefferies continued his comedy onslaught around the world.  Nobody compares to Jefferies when it comes to telling it like it is, and making us laugh at ourselves and our poor decisions. Jim Jefferies is at the top of his game (so far) and we have a feeling there is much more to come. Jefferies opens his latest special, Freedumb, taking on the issue of Bill Cosby front and center. He pulls no punches hitting that and plenty of other controversial topics. He is fearless. He doesn’t care if you hate him. He doesn’t care if you send hate mail or post on social media. It’s okay if you get offended. He wants you to.

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