49. Rick Ducommun: Piece of Mind
One of the lesser-known names on the list, you might recognize Ducommun from his supporting roles in films like The ‘Burbs, Die Hard, Groundhog Day, and Scary Movie. But he was also a helluva good stand-up, and his 1989 HBO special Piece of Mind is not only explosively funny, but it’s got a weird, non-linear meta-narrative framework that makes it play like a stand-up special directed by Charlie Kaufman.
48. Louie Anderson: “Mom! Louie’s Looking at Me Again!”
Too much of today’s audience knows this comic heavyweight from his uninspired turns on terrible television like Family Feud and Celebrity Diving. But in his day, he was an inspired comic in the Bill Cosby mold: a gentle yet endlessly funny storyteller with a specialty in family-based, childhood-memory comedy. This 1989 Showtime special captures him at his peak, and his Thanksgiving dinner and garage-saleing-with-Mom bits are unsung classics.
47. Whoopi Goldberg: Fontaine… Why Am I Straight?
Whoopi — who, lest we forget, used to be very funny — followed up her 1985 breakthrough special (more on that later) with this HBO hour in which she resurrected one of the earlier show’s most popular characters, the street-smart junkie (now in recovery) Fontaine. The line between the character and the performer is mighty thin, though, and this hour is mostly a showcase for the edgy topical comedy that was, for a time, Goldberg’s bread and butter.
46. David Spade: Take the Hit
Spade has done so many forgettable TV projects and terrible films for the Sandler factory that it’s easy to forget what a crisp, spiky stand-up he is. This 1998 HBO hour finds him in wonderfully smarmy yet personal form, joking sharply but amiably about his “dirtbag” childhood in Arizona, his deadbeat dad, and his romantic woes.
45. Bobcat Goldthwait: “Is He Like That All The Time?”
Goldthwait’s profile was so high as the screeching co-star of the Police Academy movies that he never really got credit for the brilliance of his stand-up act, where the gimmick of his persona hid a finely-tuned sense of political and social satire. Now that he’s getting respect as a filmmaker, it’s high time to reassess his stand-up, starting with this masterful 1989 hour for HBO.
44. Dennis Miller: Mr. Miller Goes to Washington
I known, I know. Since 9/11, Miller has repurposed himself as a far-right loon, spewing bile on talk radio and kibitzing on Fox News with Bill O’Reilly — which would be fine if he were still funny. But he was once not only very funny indeed, but an equal-opportunity satirist, mocking Republicans and Democrats with equal vigor. Why, this riotous 1988 HBO hour — his first of many for the network — even finds him (gasp) giving the business to Ronald Reagen. Don’t tell O’Reilly!
43. Brett Butler: The Child Ain’t Right
Butler’s dirty yet dry Southern wit got sanitized and defanged on her briefly popular ABC sitcom Grace Under Fire, but before that show’s debut, she crafted this rollicking 1993 Showtime special. Give it a watch sometime, and try to figure out why this wry talent disappeared so quickly.
42. Reggie Watts: Why Shit So Crazy?
The incomparable Reggie W. is one of those occasional figures who redefines what a comedian is and does; this 2010 Comedy Central special finds him fusing the persona of comic, musician, and rapper, fuzzing the boundaries to create something altogether new and remarkable.
41. Denis Leary: No Cure for Cancer
Say what you will about the (ahem) influence of Bill Hicks, but Leary’s furious, smoke-spewing rants on drugs, cigarettes, vegetarians, rock music, and death were pointed, funny, and often inspired — and never more so than in his breakthrough 1993 Showtime special.
40. Rob Delaney: Live at the Bowery Ballroom
Everyone’s favorite Twitter comic finally gets the showcase he deserves in this 2012 Netflix special, turning his wife’s pregnancy, his recent fatherhood, and his testicular cancer scare into an honest, odd, witty, and very funny hour.
39. Lewis Black: Black on Broadway
Though still getting it done, Lewis Black has had some trouble keeping his topical comedy pointed in the Obama era. No, he was at his best when targeting his nemesis, George W. Bush, which he does with frequency in this 2004 HBO hour. But it’s not all Bush-bashing; his bits about corporate greed, bottled water, taxes, travel, and soy milk (which, he notes, isn’t milk but soy juice) are as good as he gets.
38. Kevin Hart: Seriously Funny
Hart has managed to keep the theatrical stand-up concert film alive almost single-handedly, racking up impressive grosses for Laugh at My Pain and Let Me Explain. The groundwork for those films (and the giant tours that preceded them) is laid in this 2010 special, which finds Hart honing his candidly confessional style to perfection.
37. Patrice O’Neal: Elephant in the Room
The late, great O’Neal had a raw and sometimes uncomfortably candid voice, working through his personal demons in a style that recalled Richard Pryor at his most confrontational. This 2011 special pulls no punches, examining sexuality and relationships with honesty and freshness.
36. Jim Gaffigan: Beyond the Pale
It’s the one where he does the Hot Pockets bit. What else do you need to know?
35. Robin Williams: Live at the Met
“Pavarotti’s at the Improv going, ‘Two Jews walk into a bar.’” Williams was fully aware of the incongruity of doing his raunchy stand-up act at the Metropolitan Opera House, but the giant venue is actually a perfect fit for the big, fast, motor-mouthed comic, whose schtick hadn’t yet worn out its welcome when this riotously funny special hit HBO in 1986.
34. Kristen Schaal: Live at the Fillmore
The structure of the TV stand-up special (opening “sketch,” big entrance, up-close photography, cutaways to hysterical audience members, big finish, return to the opening sketch) is so tried and true that there’s something sort of daring about anyone who shakes it up. Bob’s Burgers and Daily Show fave Schaal did just that — boy, did she ever — in her Comedy Central special earlier this year, a brilliant bit of Andy Kaufman-esque performance art with a staged (yet seemingly very real and uncomfortable) bombing and audience revolt. The peculiar reaction from its television audience confirmed that stand-up fans can be a surprisingly conservative bunch — Schaal is taking real chances here, and in doing so, creates one of the most memorable comedy hours in recent memory.
33. Wanda Sykes: I’ma Be Me
The very funny Ms. Sykes turned out a steady stream of excellent specials in the 2000s, but the best was the most recent (dating to 2009 — can we get a new one out, stat?). It’s her most political — still basking in the glow of the Obama inauguration, and riffing hilariously on her semi-notorious gig at Obama’s first White House Correspondents’ Dinner — and most personal as well, talking at length about coming out as a lesbian, but with a light touch and deft comic instinct that makes the material smart yet never preachy.
32. Bill Burr: Let It Go
Massachusetts-bred comic Burr (familiar to Breaking Bad fans as Saul Goodman “associate” Kuby) has a tough, no-nonsense style and an endearing lack of patience onstage, and this 2010 Comedy Central special finds him in top form, with inspired bits on swine flu, chain stores, television commercials, and much more. He’s an observational comic with an edge, in the George Carlin tradition, and earns that comparison in spades here.
31. Colin Quinn: Long Story Short
This viewer was never much of a fan of Colin Quinn’s work on either Saturday Night Live or his flat Politically Incorrect rip-off Tough Crowd, which is why it was such a treat to so thoroughly enjoy this 2010 special, taken from his one-man show (directed, on and off-Broadway, by Jerry Seinfeld). Quinn presents what amounts to the history of the world in 75 minutes, starting with broad concepts and then narrowing them into specific — and often contemporary — incidents and ideas. This is the most polished and thoughtful material he’s done, the unexpected introduction of modern mores and 21st-century thinking into historical events a comedic gift that keeps on giving.
30. Chris Rock: Kill the Messenger
Rock’s 2009 special uses an ingenious editing gimmick: to convey the scope of the world tour it was culled from, crews recorded three separate shows on three continents — one in London, one in Johannesburg, and one in New York City. The three performances were then spliced together to form one performance; Rock will, say, start a joke in New York and then deliver the punchline in London before doing a topper in Johannesburg. It’s a cool, unique lark, but you stop even noticing after a while, since (as per usual with Rock) the material is endlessly funny — particularly his inspired riffs on the 2008 election.
29. Steve Martin: On Location
This early installment of HBO’s signature stand-up series catches Martin just as he was about to explode (itself a moment captured later on this list). In this intimate, club-taped show, Martin juggles, plays his banjo, gets “happy feet,” and does much of the material from his Let’s Get Small album. But hearing Martin and seeing him work are two very different things — this is inspired silliness, delivered with the grin of a talent who was just about to become an industry.
28. Richard Pryor: Live and Smokin’
As mentioned in the intro, the bulk of Pryor’s filmed material was for his amazing trio of theatrical “in concert” movies (Live in Concert, Live on the Sunset Strip, and Here and Now). That leaves only this oft-forgotten film, shot at the New York City Improv in April 1971 but not widely seen until a mid-‘80s video release. He seems thrown by the cameras, mentioning them frequently, and his set doesn’t have the tight brilliance of his later movies — he seems (in places) uncertain, tentative, still finding his voice. And that is, perhaps, what makes Live and Smokin’ so extraordinary for Pryor fans and students of stand-up. Few comics were more distinctively themselves than Pryor, and the chance to see him at this unpolished, embryonic (but still very funny) stage is rare and rather remarkable.
27. On Location: George Carlin at Phoenix
George Carlin’s relationship with HBO Comedy was a long and fruitful one — from 1977 to 2008 (the year of his death), he turned out 14 specials for the network, and just about all of them are brilliant and funny enough to make this list. But we’ll share the praise and just pick two: one (to come) from his later, grouchier years, and this earlier one, capturing his quirky observational style. Carlin shot it in 1978 in Phoenix, Arizona, in an in-the-round setting that finds him engaging his audience with his unique blend of “did you ever notice” relatability and borderline surrealism. It’s such an iconic special, in fact, that Louis C.K. returned to the venue for his most recent HBO hour, Oh My God.
26. Louis CK: Live at the Beacon Theater
Like Carlin, pretty much everything Louie has done deserves a spot on this countdown; he’s been on a remarkable run of brilliant, insightful, side-splitting specials. But his 2011 special Live at the Beacon Theater is remarkable for both its contents and its delivery; Louie circumvented the usual distribution models to take the special straight to the fans, selling it directly to viewers, via his website, for just five bucks. It performed far beyond expectations — partially because it was a smart thing to do, partially because it contains some of his wisest and funniest material, countering topics typical of modern stand-up (sex, drugs, aging, parenthood) with self-reflective bits about his own selfishness and desire to be a better human being.
25. Damon Wayans: One Night Stand
Though he taped two very good follow-up hours in the ensuing years, nothing Wayans has ever done quite matched the sheer force and energy of his debut stand-up special on HBO’s anthology half-hour One Night Stand, during that show’s inaugural 1989 season. Predating even his breakout on brother Keenan’s In Living Color, Wayans was so intimidatingly good that even stand-up maestro Eddie Murphy told Arsenio Hall that Wayans was the reason he was afraid to go back out as a stand-up.
24. Ellen DeGeneres: Here and Now
The following year, One Night Stand gave America its first good look at a charming blonde observational comic with a rather unfortunate early-‘90s mullet. Ellen DeGeneres had a quirky style and distinctive charisma that would serve her well throughout the decade the followed, as she took the traditional paths to television series and film. But it is this 2003 special that finds her at her comic peak, discussing everything from yogurt to sexuality (which would become so much a part of her public persona after coming out in 1997).
23. David Cross: Let America Laugh
The immediate aftermath of 9/11 was a weird time to be a political comic — seldom have the boundaries of what people did and didn’t want to hear seem so impenetrable. (Even George Carlin had kind words for the job performance of George W. Bush in his fall 2001 special, though he couldn’t resist joking, “Someday, we oughtta think about electing that guy president.”) But Mr. Show’s David Cross wasn’t having it; his 2002 album Shut Up, You Fucking Baby! and this accompanying tour/concert film captured the troublesomely flag-waving national zeitgeist with appropriate anger and cynicism.
22. Comic Relief
These occasional benefits for Americans in need aren’t always a laugh riot — it’s a telethon, after all, so there are serious interludes, and its three regular hosts (Billy Crystal, Whoopi Goldberg, and Robin Williams) have all become less funny (at differing rates of speed) over the years. But the original 1986 show, which aired on HBO, was full of memorable moments: a killer opening with multiple character turns by the hosts, a Sid Caesar/Carl Reiner reunion (with the former playing “Professor Ludwig von Knowitall); a surprisingly funny stand-up turn by Jerry Lewis; a Martin Short/Catherine/O’Hara/Harold Ramis Second City sketch; Bobcat Goldthwait doing his act in an on-stage shower; and, best of all, George Carlin performing “A Place for My Stuff.”
21. Robin Harris: One Night Stand
Wide-eyed, cynical storyteller Robin Harris died in March 1990, just as his star was on the rise with appearances in Harlem Nights, House Party, and Do the Right Thing. He only left one stand-up special, but it’s a doozy — an unforgettable half-hour installment of One Night Stand, concluding with his signature bit, the story of a disastrous trip to Disney World with “Be-be’s Kids.”
20. Patton Oswalt: No Reason to Complain
Oswalt spent much of the early 2000s quietly making a name for himself as a comedian’s comedian — sharp, funny, goofy, and brilliant. This 2004 Comedy Central special was his first hour-long show (after half-hours on CC and HBO), and it captures some of his finest material: Black Angus, homoerotic ‘80s music videos, “Dr. Pepper” the heroin-addicted open mic comic, NPR’s poor music choices, Stella D’oro Breakfast Treats, and true crime television. His follow-up specials, My Weakness Is Strong and Finest Hour, are outstanding as well, but this is Patton at his best.
19. Maria Bamford: The Special Special Special!
If you think Sarah Silverman’s decision to shoot her new special for an audience of 39 was too grand and not quite intimate enough, we direct you to this recent VOD hour by the wonderfully weird Maria Bamford, performed in front of an audience of two. And it’s a tough crowd: her parents, frequently discussed during the act in question. The results are fascinating — a sly commentary on the thin line separating life and art. (Plus, y’know, funny.)
18. Sam Kinison: Breaking the Rules
Like Eddie Murphy’s ‘80s work, the homophobia of Mr. Kinison’s act has not aged particularly well. And like Murphy, even that objection doesn’t subtract from the considerable brilliance (and undeniable influence) of his comedy — particularly with regards to this, his first HBO hour, before the “rock star” excesses took over both his personal life and his onstage act. In this explosively funny hour, the former Pentecostal preacher takes on the Bible, organized religion, and his ex-wives with equal furor. A portrait of a ground-breaker, alive with the rawness of comic discovery.
17. Mike Birbiglia: My Girlfriend’s Boyfriend
Birbigs isn’t just any stand-up; his most recent special (recorded for Netflix earlier this year) was honed in New York clubs and perfected during an off-Broadway run. As with his previous one-man show, Sleepwalk With Me, My Girlfriend’s Boyfriend utilizes an innovative, circular construction and careful pathos (along with Birbiglia’s shambling charm) to tell a story that is at once painfully confessional and hysterically funny.
16. Whoopi Goldberg: Direct from Broadway
In fall 1984, director Mike Nichols took then-unknown Whoopi Goldberg’s collection of character monologues to Broadway for a six-month run. Steven Spielberg saw that show and offered her the leading role in The Color Purple, and the rest is history. But more importantly, HBO’s cameras recorded the performance, capturing the multi-talented Goldberg playing everyone from a Jamaican housekeeper to a Valley Girl to a child to Fontaine, a streetwise junkie whose trip to Amsterdam takes an unexpected turn. Funny, challenging, and occasionally heartbreaking, it plays today as a reminder of the talent being wasted every day on The View.
15. Zach Galifiankis: Live at the Purple Onion
This 2007 DVD remains, far and away, the finest showcase for the idiosyncratic comic genius of Mr. Galifianakis, who does a screamingly funny set at the legendary San Francisco club, trotting out his trademark piano one-liners and easel bits, as well as some first-rate crowd work. In between, he also plays his uptight, Christian conservative brother “Seth Galifianakis,” interviewed by former Daily Show correspondent Brian Unger. The temptation of untold riches from endless Hangover sequels may have sidelined Galifianakis as a stand-up, and that’s a shame; as this disc proves, he’s one of the most unpredictable and talented comics in the game.
14. Steven Wright: A Steven Wright Special
Amongst the loud likes of contemporaries Kinison and Goldthwait, Boston comic Steven Wright came up with the simplest and most effective of ‘80s stand-up gimmicks: arid dryness. With a deadpan persona that makes Buster Keaton seem comparatively animated, Wright quietly delivered a cascade of surrealist one-liners that made him a comic legend. He’s done frustratingly few specials over the course of his long career, and the best is still his first, a 1985 HBO hour that remains timelessly, hilariously funny.
13. Robin Williams: An Evening with Robin Williams
When Williams was at his peak, nobody was better, his rapid-fire jokes and lightning-fast improvisation aiding a keen sense of social satire. This 1982 HBO special catches him at that peak (quite possibly with the aid of a bit of the ol’ “Peruvian Marching Power”), with a memorable performance on his home turf of San Francisco. The Reagan administration material and other topical references still work, but what’s most remarkable is his audience improvisation; he riffs and vibes with jaw-dropping skill.
12. Dave Chappelle: Killin’ Them Softly
Chappelle burst onto the stand-up scene with the skill and confidence of a prodigy; I still vividly remember how he appeared at Comic Relief VI, a 20-year-old ball of laid-back comic dynamite, and walked off with the show. His 2000 HBO special Killin’ Them Softly is solid from beginning to end, but it features one of his unquestionably iconic bits: the hilarious tale of a 3am visit to the ghetto in the back of a limo, and his encounter with a streetwise baby.
11. Bill Cosby: 49
Because I get worked up about such things, I’m irritated by all the press insisting that Far From Finished is “Bill Cosby’s first stand-up special in 30 years!” That’s incorrect, because a) Himself wasn’t a “special,” it was a theatrically released motion picture, and (more importantly) b) that timeline completely ignores Bill Cosby: 49, a marvelous 69-minute Cosby special released straight to VHS by Kodak back in 1987. The show captures the comic on the edge of turning 50, and most of his material is about approaching that milestone: changes to his body, his health, his eyesight, his eating habits, and so on (much of which he transcribed in his bestselling book Time Flies). But the best bit comes at the end: a 15-minute story about how he went into the Navy, and his first night there. It’s the kind of almost-rambling storytelling that would come to define his act in the years to come; it’s also the Cosby classic that should have been, a long, searching, deeply personal story that is fall-down funny and remarkably evocative, all at once.
10. Janeane Garofalo: HBO Comedy Half Hour
Garafalo’s reign as ‘90s It Girl was in full effect when HBO aired this half-hour special in 1995 (just before her breakout in The Truth About Cats and Dogs). In the compact show, she covers pop culture, dating, feminism, and sex (I can’t describe exactly why the “STOP FUCKING ME” bit is so funny, but it is), with cynicism and wit in a loose, disorganized style. It remains a funny show, and perfect snapshot of the transformations happening in stand-up at that moment.
9. Paula Poundstone: Cops, Cats, and Stuff
Poundstone has always been a gifted observational comic — her description of the inarguable train of logic that inevitably leads her to eating an entire box of Pop Tarts in one sitting is, I’m sorry, genius (and sadly accurate). But this 1990 special captures her unequaled skill with audience participation, embarking on a round of crowd work that’s funnier than most comics’ best scripted material.
8. Steve Martin: A Wild and Crazy Guy
Martin was quite possibly stand-up comedy’s first “rock star”—successes like Bill Cosby or Don Rickles played theaters, but when Martin blew up, he was playing arenas. It was all a little silly, a goofy guy in a white suit with an arrow through his head, playing the banjo and juggling on the massive stage of the Universal Amphitheater — and that’s what’s great about this 1978 NBC special (which mixes that material with taped sketches). The self-reflexive nature of his act is taken to its most absurd point, and the material is performed to perfection.
7. Bill Hicks: Revelations
It almost seemed as though the bold, confrontational, and thought-provoking Hicks had to get the hell outta the States to look at his home country with proper cynical detachment, and that’s what happened in the early 1990s, when he toured the United Kingdom and made the Revelations special for Channel 4. It ended up being the best special of his tragically short career, an angry, jaded, blistering look at the nonsensical injustices of the world and the unaccountably stupid people who inhabit it.
6. Eddie Izzard: Dress to Kill
Izzard had made a name for himself in the United Kingdom throughout the ‘90s with a series of brilliant one-man shows, in which he looked at the history of the world and contemporary mores through his intelligently silly lens. But his worldwide breakthrough came in 1999, when a San Francisco engagement (presented by Robin Williams) of his one-man show Dress to Kill was taped by HBO. The result is one of the finest specials in their history, a jolly jaunt through all of civilization, with a very funny transvestite leading the tour.
5. Rosanne Barr: The Roseanne Barr Show
Barr was a top-notch road comic and Tonight Show favorite when she landed her first HBO special in 1987. It was the culmination of her act and persona, as a bitter, smartass “domestic goddess” who did not suffer fools (like her husband and kids) gladly. Explosively funny from beginning to end, it caught the attention of Cosby Show executive producers Marcy Carsey and Tom Werner, who adapted that persona into Roseanne the following year.
4. Eddie Murphy: Delirious
Some of the material (particularly the tired anti-gay stuff) hasn’t aged all that well — and neither has that red leather suit. But few hours of television are as revered among young comics as Eddie Murphy’s 1983 HBO special, featuring such classics as his riffs on pop singers, his memories of ice cream trucks, and the story of his drunken father acting out at family cookouts. A mere 22 years old at the time of its recording, Delirious grabs the hot young comic at his cockiest and funniest, before years of paycheck roles and family comedies sanded down the fascinating rough edges on display here.
3. George Carlin: Jammin’ in New York
I might be in the minority on this one, but I actually prefer grouchy, angry, nihilistic older George Carlin to his quirky hippie younger counterpart. That variation of his persona had peeked out in earlier specials like Doin’ It Again and What Am I Doin’ in New Jersey, but it was fully formed and raging in this priceless 1992 HBO special, where he takes on such topics as the war in Iraq (the first one, that is), environmentalism, and golf. But most memorable is his epic riff on the insanity of airline announcements; do yourself a favor and cue that one up before your next big trip, and marvel at how George is still killing it.
2. Louis C.K.: Chewed Up
After the failure of his HBO sitcom Lucky Louie, Louis C.K. decided to refocus on his stand-up act, working to become the best road comic in the country. And he proceeded to do just that. His second hour-long special, which aired on Showtime in 2008, finds him truly hitting his stride, taking on language, health, race, women, and 9/11 thoughtfully and uproariously. But his best material is the middle slab about fatherhood, wherein he finds a perfect mixture of wonder and bitterness at his kids — and their bullshit. Chewed Up was recorded on March 1, 2008, the same night that George Carlin recorded his final hour; it feels like the night that the baton was passed, and that Louie took over the televised stand-up dynasty that Carlin had cultivated since the 1970s.
1. Chris Rock: Bring the Pain
Chris Rock spent most of the early ‘90s sorta phoning it in on Saturday Night Live, a show that never quite knew what the hell to do with him; after leaving SNL, he did a brief stint on the well-past-its-prime In Living Color before going back out on the road and discovering that he’d kinda lost his chops as a stand-up comic. Some performers might have coasted, or thrown in the towel. Instead, Rock buckled down, rebuilt his act and persona from the ground up, and roared back onto the scene with the finest comedy special ever made, bar none. 1996’s Bring the Pain found Rock combining social commentary, personal introspection, and comic performance with a skill and finesse unseen since the glory days of Pryor; it brought the comedian back from the professional dead, and reminded us all of what the stand-up form was, and what it could be.