The 20 Greatest Standup Specials of All Time

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.

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