The 20 Greatest Standup Specials of All Time
Modern standup has been around in one form or another since vaudeville, but it’s only been since the late ‘70s that the standup special has gained traction as the crowning achievement of a successful comic. Fortunately, the beginnings of the standup special were as fertile as rock ‘n’ roll’s birth 25 years prior, with many of the all-time greats setting templates right from the start.
The material always comes first, of course, but as a video document of a honed act it’s also important to appreciate the visual elements — the framing, editing, and backdrop — and how they enhance or detract from the pacing and quality of the jokes.
Whether it was released on HBO or Netflix, streamed or screened theatrically, filmed specials remain arguably the most accessible example of standup. Here are the best of the best.
20. Eddie Izzard, Dress to Kill
Seeing Izzard’s “male lesbian” one-man show in 1998 was just as important as hearing it, and on this Robin Williams-presented HBO special Izzard has his way with global culture, whether he’s comparing “Scooby Doo” characters to Shakespeare’s or hilariously imitating the body language of people singing the National Anthem. A tour de force of assured monologues and insightful cultural critique.
19. Mike Birbiglia, My Girlfriend’s Boyfriend
Improving on his breakthrough show Sleepwalk With Me, My Girlfriend’s Boyfriend captivates with Birbiglia’s perpetually put-upon storytelling voice, something of a cross between a personified This American Life and a classic, Bob Newhart-style account of romantic peril. This 2013 Netflix special will soon be turned into a narrative film, but it likely won’t be as achingly funny as this unadorned special.
18. Whoopi Goldberg, Direct From Broadway
This collection of funny and biting character monologues, which dips a bit with a surfer girl passage but mostly hums with a stunning theatrical mastery, is helped greatly by director Mike Nichols, who expertly frames Goldberg as the bold, can’t-take-your-eyes-off-her talent she was in 1985.
17. Zach Galifianakis, Live at the Purple Onion
Animated and unhinged, Galifianakis turns the intimate San Francisco club The Purple Onion into a therapy session that’s by turns cathartic and confrontational, but always laugh-out-loud funny. His acting career may have swallowed his standup shortly thereafter, but the experimental, wall-breaking humor here is endlessly compelling. Even after repeated viewings, the constantly-shifting structure leaves you wondering what Galifianakis is going to do next. Extra points for the out-of-nowhere choir-boy finale and intercut interviews with his “brother” Seth.
16. Roseanne Barr, The Roseanne Barr Show
The most groundbreaking comedy is funny while spotlighting an underrepresented viewpoint, and Barr’s blue-collar (but never mindlessly pandering) perspective spoke for millions on this 1987 special, which remains the best example of her influential act. A marvel of laidback sarcasm that plays like a pissed-off answer to the whiny victimization of a lot of dad comics’ family-based material.
15. Mitch Hedberg, Comedy Central Half Hour
It’s a tragedy that Hedberg’s first marquee TV special was his last, but this 2003 show, which includes material from Mitch All Together, nonetheless remains compelling evidence for The Cult of Hedberg, which continues to (rightfully) worship him for his effortless cool and funhouse mind. Few comics, save for Carlin and his acolytes, dissect and elucidate the absurdity of language as brilliantly as Hedberg.
14. Maria Bamford, The Special Special Special!
Another argument for why Netflix has supplanted HBO, this 2012 special spotlights Bamford’s improbably malleable voice and fascinating, troubled brain, which was recorded in her living room with only her parents as audience members. The awkward gimmick works surprisingly well as the Comedians of Comedy veteran nails material that embraces depression, weird food, and (implicitly) our crumbling, schizophrenic world.
13. Janeane Garofalo, HBO Comedy Half Hour
This relatively unassuming 1995 special caught Garofalo at the perfect moment: she was already a known quantity thanks to The Ben Stiller Show and Reality Bites, but her self-effacing standup had yet to transform into the meandering, self-obsessed stuff that has given fuel to her critics. Along with Mr. Show and a handful of others, Garofalo’s vicious, deadpan sarcasm here defined and popularized alt-comedy before many people knew what it was.