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.

12. Bill Hicks, Revelations

As one of the most technically dazzling comics of his era, Hicks’s marvelous pacing and tone always worked in conjunction with his material, which remains ahead of its time. Like a disappointed but fired-up philosopher, Hicks uses this 1993 London-filmed special to opine on all manner of injustices and hard truths, from the evils of war and propaganda to famous bits on religion and psychedelic drugs. Its weird cowboy intro notwithstanding, Revelations is about as straightforward and ballsy as standup gets.

11. Steven Wright, A Steven Wright Special

Before Tig Notaro, Todd Barry, Demetri Martin, or Mitch Hedberg, Steven Wright was dropping weird, insanely clever (or, often, just insane) one-liners that relied as much on their content as his uniquely monotone delivery. That this 1985 HBO hour (his first) remains so consistently funny is testament to the durability of his ideas and the fact that no one, in any era, has matched his style. Like Mark Twain or Kurt Vonnegut, Jr., however, the economy of this Boston-bred comic’s material is staggering. No other standup can make such dry delivery feel so spiritually nourishing.

10. Paula Poundstone, Cats, Cops and Stuff

She may have only been 31 at the time of its taping, but on this 1990 HBO special Poundstone comes off as impossibly wise while matter-of-factly discussing cats, Daryl Hannah’s weird gate, Pop Tarts, Texas, and even the askew fashion of a random audience member. If she were a guy and spoke slower, Jim Gaffigan wouldn’t have an act.

Few comics can read and respond to the energy in a room as expertly as Poundstone, and this show, recorded in San Francisco, proves she’s been owning it for decades. Anyone looking for a manual on crowd work should commit this to memory.

9. Bill Cosby, Himself

No comic had made parenthood’s endless absurdities as appealing and relatable as Cosby, so it’s unsurprising that 1983’s Himself essentially previewed what was to come on the long-running, quietly revolutionary The Cosby Show. This humbly presented act from the sit-down standup (he rarely leaves his seat in the nearly two-hour film) is the ideal example of Cosby’s vaunted ability to uncover hilarious truths in daily indignities.

Remarkable, too, was what Cosby represented at the time amid the explosion of a new, harsher style of standup – and one he unintentionally helped father. Then as now, the lack of topical humor and vulgarity makes Himself a perfect catalog of Cosby’s inner dialogue, a deceptively gentle turn from a master orator and humorist that will likely hold up as well in 50 years as it does today.

8. Dave Chappelle, Killin’ Them Softly

What is it about recording comedy specials in Washington, D.C.? Like hardcore punk, the best comics have used the setting to rail against inequities – in this case, racial and cultural – while watching the resulting friction and sparks light even deeper fires. Killin’ Them Softly contains the best of Chappelle’s pre-TV series material performed with a relaxed but honed voice, crossing over from bit parts in films (and the cult stoner flick Half Baked) to a full-fledged comedy giant.

Like Pryor and Murphy before him, Chappelle’s ideas on race have since become embedded in the national consciousness, shining a light on the underlying dynamics of oppression and the painfully hilarious (but mostly just painful) ways in which they’re expressed. Recorded at D.C.’s Lincoln Theatre in 2000, Killin’ Them Softly brought everyone into the conversation and gleefully collapsed the distance between Chappelle’s perspective and the world around him.

7. Robin Williams, An Evening with Robin Williams

Williams’s shows, at any age, were tour de force spectacles of pinball logic and breathless impressions. But when good material collided with Williams’s seemingly inexhaustible energy, the result was something transcendent.

This 1982 HBO special, recorded in San Francisco’s Great American Music Hall, reeks of its time – check out those shiny black pants and the Reagan material – but also rises above it with Williams’s otherworldly skill for crowd work and improvisation. As many critics pointed out after his recent suicide, Williams’s barely-controlled hurricane act often showed its brilliance when given just the right creative constraints. An Evening With is just that: a master class in comedic politics, character studies, and silly, profane flights of fancy made all the better by its intimate staging.

6. Louis C.K., Shameless

The most visible comic of the moment set the stage for his ascendance with a series of rock-solid specials, including 2006’s effortlessly assured Shameless. C.K. himself might be the first to mock his not-so-riveting stage presence, but here his malleable expressions and surprisingly physical performance make the rampant misanthropy all-the-more appealing.

Given its mix of outrageous material (think barrels of duck vaginas and AIDS trees) and plainspoken cultural jabs, Shameless bears the deceptive stamp of a free-form conversation. But since C.K. is unmatched at taking dumb, angry ideas to their (il)logical conclusions, waiting in line at the post office becomes a scat-torture fantasy, and a soon-to-end marriage the platform for rattling off a variety of sexual dysfunctions. Cringe-worthy, feral, and brilliant from start to finish.

5. Eddie Murphy, Delirious

Building on the groundbreaking material, profanity, and stage prowess of the previous decade’s standup innovators, Murphy took the comedy special to new heights in 1983 with a generous helping of rock star charisma.

There’s little to no neurosis in Delirious, a title that accurately captures the then-22-year-old Murphy’s raging ego and lumpy material as much as his appealing physicality. Recorded at Washington, D.C.’s Constitution Hall and aired on HBO, Delirious is not the best example of standup writing, or even a particularly flattering example of the early ‘80s cultural mindset. Unironic bits on “faggots” and a general, running homophobia, for example, have aged terribly.

But when Murphy was good – as when describing his drunken father, or reenacting the uncontrollable joy that children feel when confronted with an ice cream truck – he swerved and kicked like a downed power line, intimidatingly energized and liable to come after you next. Despite the dissonance between the quality of the material and the quality of the performance, Delirious is required viewing for standup fans who wonder where the tone, pacing, and visceral performance style of many of today’s best comics originated.

4. Steve Martin, A Wild and Crazy Guy

Martin’s 1978 NBC special, which featured not only bits from his arena-filling standup set but sketches with celebrity guests like Johnny Cash and George Burns, is exceptional on a number of levels. It’s an example of kind-spirited humor that still manages to be surreal and groundbreaking. It’s also an exception to the idea that comics must continually build up to their best work with complicated, life-threatening personal tumult.

Martin’s fame at the time no doubt gave him a good deal of creative control, but he nonetheless undermines variety-show cliches and live-comedy expectations in equal measure on this network curio. It’s pretty much impossible to find this as it originally aired, save for an old VHS copy, but 2012’s The Television Stuff DVD boxed set presents the material that comprises it: the sketches, plus the exemplary Universal Amphitheatre set that provided the standup footage.

Even the seemingly slight moments of A Wild and Crazy Guy – such as Martin’s mock outrage at the audience misinterpreting his use of the word “pussy” (following a character-heavy treatise on sex and dating) – continue to resonate. It’s as charming as Martin’s overall standup career was influential and criminally short-lived.

3. George Carlin, Carlin at Carnegie

Carlin’s prolific nature makes it nearly impossible to pick a defining work. His 1977 USC performance crackles with youthful electricity as much as 1992’s (relatively) mature HBO special Jammin’ in New York showcases his growth, aggression, and stage mastery. But when it comes to classic Carlin, this 1983 HBO special is a perfect mix of his fierce social critiques and casual, devastating wit.

Dressed like a Sesame Street extra on a stage covered in a massive rug and backed by towering stacks of wooden chairs, Carlin lays bare the artifice and contradictions of Comfortable America. His loose-limbed impressions, bug eyes, and Noo Yawk accent help sell bits that range from pet psychology and abortion to an updated “Filthy Words.” The dynamic set dressing makes it look like an academic lecture as daydreamed by stoned, goofy intellectuals.

Like plenty of other defining moments in artistic careers, it’s a return to form for Carlin after a trip through the ringer – in this case, stepping away from constant touring in the late ‘70s and recovering from a series of heart attacks. Carnegie also plays like an hour-long highlight reel (sans jarring edits) by presenting a tight version of material from Carlin’s ninth album, A Place for My Stuff, while working in a greatest hit or two. Fortunately, the man’s legendary ability to find philosophical truths by dissecting, for example, the habits of fussy eaters has never been stronger.

2. Chris Rock, Bring the Pain

Like Dylan plugging in at the Newport Folk Festival, the (then) 31-year-old Rock shattered expectations while reinventing his persona on Bring the Pain, a commanding example of what happens when a middling sketch player and actor throws everything away to focus on writing and performing material that matters to him.

Filmed at Washington, D.C.’s Takoma Theatre, Bring the Pain is the result of two years of laser-like focus following 1994’s underwhelming Big Ass Jokes, which itself followed Rock’s disillusionment from Saturday Night Live and other TV/film projects. At the start of the hour, Rock swaggers out of his dressing room onto a stage bearing his giant initials, dressed all in black, grinning.

He wastes no time in savaging idiocy and hypocrisy, from in-the-news topics like D.C. mayor Marion Berry to dating and marriage. The now-classic (and still potent) “Niggas vs. Black People” leaps out of the shadows of Richard Pryor and Eddie Murphy by subverting and exploding assumptions that many lesser comics continue to base their acts upon.

It’s easy to see Rock’s fingerprints on any number of currently active performers, from Dave Chappelle to Aziz Ansari, but what distinguishes Bring the Pain is its relentless determination to present ideas that are not only uncomfortable and brutally hilarious, but as exciting to their creator as they are to the audience.

1. Richard Pryor, Live on the Sunset Strip

At the time of Live on the Sunset Strip’s release in 1982, 42-year-old Richard Pryor was not only a veteran comic, he had already endured enough personal and professional turmoil (including a bleak upbringing, multiple divorces, addiction, fights with NBC censors, and a devastating, drug-fueled fire that almost killed him) to erase a lesser artist. But even as the backstory informs and deepens Live on the Sunset Strip, it never dominates it.

Pryor’s genius rests in part in his ability to switch moods invisibly. Filmed before an adoring crowd at the Hollywood Palladium, the special starts slow and unassuming as Pryor regains his confidence after a couple years away from the limelight. But as it picks up steam – whether in a largely improvised bit starring Pryor’s Mudbone character, or in exploring sex, race, and his life-changing trip to Africa – it develops an unstoppable momentum. Credit is also due to director Joe Layton, a Broadway and TV veteran who presents a natural mix of tight, medium, and wide shots to portray his subject’s riveting (and, at this point, more measured) stage presence in subtly narrative fashion. It helps that Pryor’s fire-red suit practically explodes against the black curtain, turning every angle into an iconic image.

On stage, Pryor is like a skinny, nervy Jimi Hendrix, an effortless physicality (see his animal impressions) and dexterity saturating the material. It’s remarkable how fresh and funny Sunset remains: It’s bawdy but full of subtext, brutally honest and personal but also thoughtful, socially conscious, and provocative. If anything even comes close to cliché or convention in this lean, 82-minute film, it’s because hindsight obscures the fact that Pryor was setting the standard in real time.

John Wenzel is an A&E reporter and critic for The Denver Post who has contributed to Rolling Stone, The Spit Take and SXSWorld.

The 20 Greatest Standup Specials of All Time