Seasons of Love: "Chappelle's Show," Season Two (2004)

This year marks the unofficial tenth anniversary of what I'll call "Chappellemania." The mid-2000s were a lousy time for TV comedy --sitcom, sketch, or otherwise-- so for that time period I'd rank Chappelle's Show up there with "Arrested Development," "Scrubs," and Bush-era "Daily Show" among the few torch-bearers of the form. As a sketch comedy in 2004, Dave Chappelle was running laps around the competition: SNL was still struggling to find itself post-Will Ferrell, and MADtv was consistently inconsistent and relying heavily on one-note recurring characters.

The story behind the Dave Chappelle's rise to fame and confusing downfall is a fable told many times, a cautionary tale of too much too soon. After years of struggling, including a procession of failed TV pilots, Chappelle became an overnight success. However, writer's block and interference from Viacom instigated an apparent nervous breakdown from which Chappelle is still recovering. He gave us two years of great sketches and pointed social commentary (let's pretend the piecemeal, mostly Chappelle-free third season didn't happen) before disappearing into the ether. He returned to stand-up in recent years a humbled family man, but it just isn't the same.

So how does "Seasons of Love" tackle a sketch comedy show? By focusing more on the individual sketches, rather than episodes. Sketch comedy is inherently uneven, so it would seem unwieldy to judge the second season of "Chappelle's Show" by looking at an entire 30-minute episode (including the obligatory music video) as a whole. The first year is fine in its own right, but I'll argue that season two is a desert-island comedy pick.

Five Favorites:

"The Racial Draft," 1/21/04. The first home run of season two comes at the tail end of the season premiere. Combining Chappelle's yen for racial humor with the bloated media spectacle of the NFL and NBA drafts, various ethnicities claim dibs on racially ambigious media figures. Come for Chappelle's goofy Tiger Woods impression, stay for the self-deprecating Wu-Tang Clan cameo.

"Black Gallagher," 1/28/04. More or less a blackout sketch, this short, sweet, and succient bit lampoons the one-joke oddity that is Gallagher. Let's just say the Slegde-O-Matic is far from what the audience was expecting.

"Charlie Murphy's True Hollywood Stories," 2/11/04. Arguably the best-known, most-loved, and most quoted sketch in the entire series, Eddie's older brother (and an okay comedian in his own right) details a nightmarish evening in 1982 with the R&B star, by then a full-blown coke addict and apparent sociopath. The madness of this particular night is augmented by commentary from the real-life James, who denies nothing ("cocaine is a helluva drug") and only intermittently seems remorseful. When James died suddenly six months later, Comedy Central conspicuously paid tribute by repeating this episode three times in the span of six hours. Pecularily, Charlie's perilous brush with fame led to...

"Charlie Murphy's True Hollywood Stories," 2/18/04. ...an encounter with Prince. Where Chappelle's imitation of Rick James vaulted the show into the pop culture stratosphere, this one-off encounter with the Purple One might have been the stronger sketch. A chance meeting at an after-party segues into Charlie and friends getting their asses kicked on the basketball court by the diminutive guitar god (Chappelle again, see above) and his puffy-shirted entourage. There was no Greek chorus here; you'd just have to take Charlie's word for it.

"Black Bush," 4/14/04. Topical sketches typically have a short shelf life, and it usually doesn't work as nostalgia. However, the last sketch of the season is a unique exception. Chappelle and crew reimagine the Bush administration's initial handling of Operation Enduring Freedom as if our 43rd president were a disingenuous black guy. (The cameo from Prime Minister "Black Blair" is a riot.) Just when it seemed like Chappelle's near-constant skewing of race relations was starting to wear thin, it roars back with a vengence.

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