Top 10 Classic Comedy Specials of The 90s
#10: “Brett Butler: The Child Ain't Right” (1993)
Although she’s best known for her starring role in the sitcom “Grace Under Fire”, Butler first found success as a stand-up comic. Arguably, it’s her stage work that best showcases her biting and satirical wit. Her 1993 special “The Child Ain’t Right” captures everything that makes her so hilarious to watch. A personable comedian with a strong connection to her audience, she possesses a manic energy on stage, but with clear lines of thought behind how her jokes and stories connect. “The Child Ain't Right” offers proof that often, stand-up comics shine best on stage!
#9: “Dennis Miller: Black and White” (1990)
Dennis Miller is the sort of comic who doesn’t suffer fools, and doesn’t care if you don’t get references that are, in his own words, “arcane.” His 1990 special, “Black and White,” was shot for HBO’s “Comedy Hour” shortly before the comic would leave his position on “Saturday Night Live.” It was indicative of the direction Miller would take on his own weekly talk show. Smart, acerbic and shot in an austere manner befitting the comparatively high brow content on display, “Black and White” is smooth like butter. Miller glides from bit to bit, hoping that his audience comes along for the ride, but perfectly ok if they just grab onto the pieces that make sense. It’s witty, razor-sharp comedy.
#8: “David Cross: The Pride Is Back” (1999)
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“The Pride is Back” was David Cross’ first full-length special, and perfectly encapsulates his unapologetic style of comedy. Cross had already seen cult success with the HBO program “Mr. Show,” but “The Pride Is Back” sees Cross truly coming into his own. The jokes vacillate between political commentary, over-the-top satire and social observations, with an underlying tone of darkness that makes the special a time capsule of late-90s edginess. Cross enlightens and offends in equal measure, and makes no apologies for any of it.
#7: “I’m Telling You for the Last Time” (1998)
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This Grammy-nominated comedy album, and its corresponding TV special, were recorded shortly after Jerry Seinfeld’s iconic sitcom went off the air. Its title signified the retirement of certain bits associated with that show, and, as a result, serves as an awesome “greatest hits” sort of presentation that’s fantastic for both new fans and old. There’s quite simply no-one who does observational humor quite like the master himself, and “I’m Telling You for the Last Time” feels just as fresh today as it did back in ’98. The television version also featured plenty of special guests, like Garry Shandling, Robert Klein and George Carlin, firmly entrenching Seinfeld alongside other greats.
#6: “Denis Leary: No Cure for Cancer” (1992)
The unfortunate elephant in the room within the world of stand-up comedy is the practice of stealing routines. Denis Leary’s “No Cure for Cancer” was hugely popular back in 1992, but accusations immediately flew that the comic was heisting the persona of cult comic hero, Bill Hicks. We’ll get to his work in a moment, but the pair were actually friends prior to the release of “No Cure for Cancer,” a relationship that effectively ended after this special. Leary is clearly doing a Bill Hicks impression here, but it’s a damn good one, with enough of his own personal spin to make “No Cure for Cancer” equally iconic. And his music video for “Asshole” still makes us laugh to this day.
#5: “Bill Hicks: Relentless” (1992)
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You be the judge: did Denis Leary steal his act from Bill Hicks? The debate is certainly valid, but perhaps a better explanation is that Leary presented Hicks’ apocalyptic, scorched-earth style of comedy, and made it commercially viable. This is because Hicks constantly challenged his audience to be on his level. He was an intelligent and savvy comedian who wasn’t afraid to delve into deep and uncomfortable places. Both his “Relentless” and “Revelations” specials speak to Hicks’ iconoclast soul, as a comedian who gleefully enjoyed skewing sacred cows.
#4: “George Carlin: Jammin’ in New York” (1992)
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When comedy legend George Carlin says that a certain special is a personal favorite, you stand up and take notice. “Jammin’ in New York” was Carlin’s favorite performance he did for HBO, and it’s easy to see why. Sure, “You Are All Diseased” from 1999 was also fantastic, but “Jammin’ in New York” possesses a dangerous, live energy that presents Carlin at his unfiltered best. George is on fire during this performance, referencing everything from conflict in the Middle East to his mistrust of the US government. There’s also space given to Carlin’s legendary word play, with enough balance of experimentalism and observational humor to make this one a classic.
#3: “Comedy Central Presents: Mitch Hedberg” (1998)
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We lost Mitch Hedberg far too young back in 2005, but at least we have classic comedy specials like this one from 1998 to remember his genius. Hedberg was labeled “the next Seinfeld” by Time Magazine at the time of his death, and it’s easy to see why. The material on “Comedy Central Presents: Mitch Hedberg” was surreal and challenging, strange and idiosyncratic, to the point where there was really nothing quite like it, both at the time and today. Mitch’s delivery was laconic and low-energy, but intentionally so, drawing on Hedberg’s quirky perspective on life to catch lightning-in-a-bottle. We miss you, Mitch.
#2: “Eddie Izzard: Dress to Kill” (1999)
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The unconquerable spirit and energy of Robin Williams loomed large over the comedy of Eddie Izzard, particularly on this special from the late 90s, “Dress to Kill.” You have to be willing to hang on for dear life during Eddie’s relentless race towards comedy gold, as this special doesn’t stop or slow down for a minute. It’s easy to get lost in Izzard’s stream-of-consciousness style of comedy that goes everywhere from existential musings to local observations and direct interactions with the audience. Izzard turns the English language into an artform here, and “Dress to Kill” continues to bear comedic fruit for everyone willing to listen.
#1: “Chris Rock: Bring the Pain” (1996)
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Chris Rock reportedly rehearsed and practiced for weeks in order to prep himself for his second HBO special, “Bring the Pain,” back in 1996. And it shows. Rock was on fire this night, and the audience definitely felt it - creating a symbiotic sort of magic that’s infectious. The special earned Rock two Emmys and a Grammy for his efforts, despite the fact the material doesn’t pull any punches. There are jokes on this special that Rock has never performed since, but that doesn’t really matter, because “Bring the Pain” exists, and for that we’re eternally grateful.
