Anyone who tells you that political correctness killed comedy is probably just not that funny. Indeed, in such dire and confusing times, we need laughter now more than ever. Here are my personal choices for the 20 funniest stand-up comedy specials I’ve ever seen. I’m generally avoiding specials that are more than a few years old because comedy does tend to age rather poorly. If you’re looking to add a little levity to your day, any one of these comedy specials is a great place to start.
Our first special may not be the most laugh-out-loud funny, but it is still one of the most joyous thanks to his teddy bear demeanor and his insistence on only doing jokes about things he loves. Often times, comedians can focus so much on what’s wrong with the world that it becomes too bitter. If you’re just looking to brighten your day and feel a bit better about the world, “Giggle Fit” is for you. Also, I hope you like weed.
Born and raised in Canada but currently based in England, Katherine Ryan brings a pretty unique perspective to this special. Jokes about how men are luxury items don’t exactly break new ground, but I don’t believe they’ve ever been made with more conviction. Her impression of her exceedingly British daughter is hilarious, too.
Birbiglia has several great specials under his belt, but for my money “Thank God For Jokes” is his best work. Meditations on growing up Catholic and the very nature of jokes themselves are just fascinating topics. The assertion that jokes should never end with “I’m joking” is a brilliant observation, and it is so true that jokes have been ruined by people who are bad at telling them. If the deconstruction of comedy’s very nature sounds interesting to you, you need to check out his podcast “Working It Out” as well.
While she’s best known for turning great personal hardships into cathartic comedy, this special is far more jubilant. Her deadpan delivery contrasts her silly jokes so well, and this special is an easy choice for anyone who’s looking to simply cheer themselves up.
As the co-creator of “Chappelle’s Show,” Brennan may have already been responsible for inspiring many of your laughs without you knowing it. Comedy specials with gimmicks can be pretty hit or miss, but this one is surely a hit. It combines traditional standup, one-liners and deeply personal stories, using three separate mics to differentiate between them. His ruminations on depression are profound and interesting, and his one-liners hit tremendously hard.
Now this is a strange pick that I definitely don’t categorically recommend, but I found it immensely entertaining. Natalie dresses as a hairy dude bro to deliver a one man show that tackles the nuances of consent in the most uncomfortable way possible. At one point she wrestles an unsuspecting man from the audience while she herself is mostly naked. It is totally valid to not find any humor in this special at all, but I think everyone should try it out of morbid curiosity alone.
The art of joke telling is in danger of becoming lost, but Morril is one of the great practitioners. There’s no gimmick, no angle, just pure stand-up. Plus, this special is on YouTube so you can watch it for free if you’re one of the few people who don’t “borrow” someone else’s Netflix subscription.
Similar to “Nate – A One Man Special,” this hour from alternative comedian Kristen Schaal is not for everyone. Some of the abstract bits go on for way too long, and I can understand not finding this funny at all. However, I absolutely loved seeing a little girl go on stage and roast the Hell out of Kristen. Honestly this special is worth the watch just for that moment alone.
No one needs me to tell them just how funny John Mulaney is, but omitting him from this list would just be irresponsible. It was really a toss up between his three Netflix specials, so this entry might as well also include “New In Town” and “Kid Gorgeous.”
While Nikki is probably at her funniest at the Comedy Central roasts, her Netflix special is still excellent. If you don’t like jokes about sexuality then you should steer clear of this one.
Remember when I mentioned earlier that comedy tends to age poorly, so I’m trying to keep my picks as recent as possible? Well this applies to O’Neal’s only full special, but I had to make an exception. To be clear, some of these bits did not age well at all, and were arguably not even permissible at the time, but if you’re not easily offended, this legendary comedian’s work should not be missed. Tragically, O’Neal passed away less than a year after the release of this hour.
It can be very easy to fixate on Wong’s pregnancy, but to do so would be to do a great disservice to the quality of her writing. Yet to ignore it entirely would be equally erroneous, as her impending motherhood was a distinctive facet of a unique special in a comedy world that’s largely dominated by men and pervasive sexism.
Oswalt is one of the most prolific and enduring comedians around, and he has many great specials that are worth your time. This one stands out for its subject matter. While he starts with some light-hearted Trump material, the latter half of this hour focuses on the death of his wife and the impact it had on him and his daughter. He is able to mine some laughs out of his tragedy and his optimistic conclusion from such a devastating event is truly uplifting.
This 4-part special is off-beat and absurdist in the best way possible. The comedically dramatized identity crisis he’s going through makes for a fascinatingly meta viewing experience, and initially baffling choices – like beginning the special kneeling – pay off in brilliantly funny ways.
This alarmingly prophetic hour came out just weeks before everything in America began to shut down due to the pandemic. Watching Maron do stand-up sort of feels like listening to your drunk uncle spout off conspiracy theories at Thanksgiving, but in a good way.
Much like John Mulaney, Chappelle’s presence on this list was an inevitability, and I could have gone with a few different choices, as he’s been quite busy over the last few years. I opted for “Equanimity” simply because of the line “It was my experience that white dinner wasn’t delicious.” I’m not really sure why that line is so funny to me, but it just is.
Dark, offensive comedy is such a mixed bag. There are numerous hack comedians out there that just say the most horrible things that come to mind for shock value, then cry about cancel culture. Jeselnik is potential evidence that cancel culture might just be a myth. His stand-up is all about the twist; he sets up harrowing premises and as a viewer you know the punchline is going to be dark, but you can never guess where he’s actually going. You can do jokes about almost anything if the jokes are clever.
While this is not a stand-up special in the traditional sense, it still made laugh about as hard as anything. Shot over three nights in New York, “Bumping Mics” is a loosely structured live show where the Roastmaster General himself Jeff Ross and the legendary Dave Attell roast each other, the audience and some special guests, and just have a ton of fun. Notable guests include Bruce Willis, Gilbert Gottfried and an exceptionally hydrated Paul Rudd.
Hannibal is just one of those comedians who is effortlessly funny. His delivery makes every line even funnier, and indeed anytime he does literally anything on “The Eric Andre Show” it’s amazing. One of my favorite jokes ever is his bit about why he doesn’t put a napkin in his lap at restaurants because he believes in himself. It’s so simple yet so good.
It’s sort of painful to know that Taylor is basically the same age as me yet is already this good at what she does. What am I even doing with my life? Existential crises aside, Tomlinson’s joke writing and delivery is so well refined that every moment of this special is great. She doesn’t exactly break any new ground, but she broaches commonly tread topics with such comedic tact that her Netflix special is truly deserving of the coveted distinction of being my favorite stand-up special. What an honor.
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