Chris Rock’s Top Five Funniest Moments In Comedy

To celebrate the launch of Chris Rock’s new comedy Top Five, we’re looking at five of Rock’s finest moments.

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Choosing just five of Chris Rock’s finest moments brings on the sort of instant-freeze terror that those who’ve received gift vouchers for Christmas may recall: where the hell do you start, and how do you choose? And how do you set the parameters for what’s considered “best” in a career that stretches back to the mid-’80s? Rock’s work, after all, continues to take in everything from biting political commentary to broad mainstream comedy; you could drill down until you were looking at the “top five Chris Rock bits about policy during the Obama administration”. But even though one man’s “In Living Color Season 5” is another man’s “[insert worst sketch show ever]”, here are five winning moments from various milestones in Rock’s career.

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In Living Color – “How Much For One Rib?” (1994)

In a rather bitter irony, my introduction to the short-lived sketch show In Living Color was via a tribute to one of its white stars, Jim Carrey; we caught a ‘best of’ compilation late at night on tele in the late-’90s. As a launching pad for a pretty extraordinary roll-call of talent (including Carrey, Jamie Foxx, Jennifer Lopez, Rosie Perez, Carrie Ann Inaba and many others), it’s near-unmatched in its era.

Rock was a special guest on the final season of the formerly Wayans-heavy show, mostly as Cheap Pete, his character from Blaxploitation spoof I’m Gonna Git You, Sucka. Here he is bargaining with the smooth, smooth tones of Isaac Hayes (who plays a presumably long-suffering restaurant owner). Rock’s best work? Probably not, but looking back, it’s not hard to be struck by the sense he was destined for big things – and it was the year he taped his first special, Big Ass Jokes.

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Bring The Pain – “Black people vs n—-s” (1996)

Rock’s second special, HBO’s Bring The Pain, marked him as one of the finest comedians in the biz. Indeed, you could do a top five moments from Bring The Pain, the number one of which is usually this routine, and with good reason: it’s still an incredibly cutting, insightful, and wildly hilarious examination of Blackness in America (not to mention introducing phrases like “low-expectation-having motherfucker” into the lexicon).

Rock almost instantly retired the bit, telling 60 Minutes some years later, “I’ve never done that joke again, ever, and I probably never will. ‘Cos some people that were racist thought they had license to say n*gger.” The special went on to win two Emmy Awards, and saw Rock compared to everyone from Richard Pryor to Steve Martin to Lenny Bruce; Bring The Pain was minted as an instant classic and was the beginning of Rock’s ascension to comedy’s pantheon.

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The Chris Rock Show – How Not To Get Your Ass Kicked By The Police (2000)

This “training video” segment from the fifth series of The Chris Rock Show went to air in October 2000, a decade after Rodney King’s assault at the hands of the LAPD, and its bittersweet satire has only increased in potency in the fifteen years since its release. In the pre-YouTube days, I saw a copy of this skit on a VHS tape; since the advent of quick-share social media, How Not has been turning up with increasing frequency, shared as a satirical – alarmingly on-point – PSA in the era of George Zimmerman and Ferguson.

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Never Scared – “Marriage” (2005)

By now well and truly a part of the comedy firmament, Never Scared was met with wide acclaim and a 2006 Grammy Award for Best Comedy Album. Rock’s bits about relationships often take a back-seat to his material about politics and race, but he remains one of the most consistently insightful comics when it comes to talking about love. In this killer rant, Rock unloads on the boredom of marriage and the inanity of long-term relationship routines. What’s in the tea? WATER, BITCH!

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Comedians In Cars Getting Coffee – “Kids Need Bullying” (2013)

There’s nothing quite like watching the behemoths of comedy shooting the shit, and we get that and then some with this episode of Seinfeld’s webseries; it’s not an exaggeration to suggest that these two are still at the very top of the top. True, both Rock and Seinfeld are more considered in the HBO special Talking Funny, but watching them free-range on everything from filmmaking to relationships to, yes, the importance of bullying in inspiring genius, all the while tearing around in a Cheese Wiz-orange 1969 Lamborghini Miura P400S, stopping off for lunch in Allendale, NJ, is a real treat.

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Top Five, starring Chris Rock and Rosario Dawson, tells the story of New York City comedian-turned-film star Andre Allen, whose unexpected encounter with a journalist forces him to confront the comedy career—and the past—that he’s left behind. The film was co-produced by Shawn “Jay Z” Carter and Kanye West, and hits cinemas on March 12.