Selecting ten stand-out sketches from (Dave) Chappelle’s Show is as fruitless as culling Trump’s talking points to their most memorable few. We would never take on such a task. Bolder folk have tried, going as far as running all twenty-eight episodes of the landmark, politically astute sketch show through a tournament in an attempt to separate the gold from the gold.
While fans continue to butt inspired heads over which dishes in Dave’s three-year feast were the tastiest, we’ve opted to count down ten of the best – not the ten best ‑ sketches from a show that ended far too soon…
The Black White Supremacist
A sketch so significant that it continues to make headlines well over a decade after it aired, Chappelle took on radical bigotry as Clayton Bigsby - a blind white supremacist who has no idea that he is black.
Above is part two. Part one is only readily available in sub-par quality, but you can squint at it here.
Tupac Is Still Alive
Still to this day, the surfacing of a new Tupac track barely raises an eyebrow. We can only assume Pac approves these releases from beyond the grave. A Shakur fan himself, here Chappelle pokes fun at the media and hip-hop industry when fresh Tupac flows hit the dance floor.
You get the sense that Dave and guest star Jamie Foxx had a ball playing with such a ludicrous premise, but don’t let the wackiness fool you – this sketch was hailed as a full-jawed bite into issues of white ownership and entitlement, as well as a megaphone for largely unaddressed feelings of betrayal amongst the people during the presidency of George W. Bush. The fact it came before the election of Barak Obama adds an additional layer of interest.
Multi-talented performer and Whose Line Is It Anyway? star Wayne Brady has a reputation for “not being black enough”. Chappelle questioned this label by enlisting Brady himself to subvert his public image as a friendly, non-threatening black man.
By turning Brady into a drive-by gangster, Chappelle questioned the public’s perception of early 2000s African-Americans.
One of Chappelle’s most famous sketches. Here, he stamps all over arbitrary rational delineations, satirising the trend for an ethnicity or nation to “claim ownership” of a public figure.
Our most famous example of this phenomenon is our annexing of New Zealand-born Russell Crowe, prompting New Zealand’s inability to let go of Australian citizen Russell Crowe.
Chappelle could make Reparations 2016 by making a few minor changes to his 2003 script, but whether Comedy Central in its current incarnation would air it is a different story. Black poverty and racial stereotyping share the spotlight in a brutal sketch from season one.
The Niggar Family
Just watch it.
True Hollywood Stories: Prince
Be sure to check out Chappelle as Rick James in this sketch’s companion, as its omission was decided using the eeny-meeny-miny-moe mode of conflict resolution.
As the pocket virtuoso prepares for a tour of our hemisphere, let this affectionate sketch fuel your anticipatory fire.
Samuel Jackson Beer
Three men order a beer with specific branding while the brand ambassador just happens to be seated nearby. Though not as hard-hitting as other bits on this list, Chappelle’s interpretation of Jackson’s persona is enough to warrant the love.
Mad Real World
As Chappelle’s Show aired during the reality TV boom, it’s unsurprising that Dave set his lasers on MTV’s ultra-white The Real World. In Mad Real World, a “white boy” named Chad enters a house full of African-American stereotypes, and his reactions are as telling as they are priceless.
Honestly, now that the list is over and we have a little clarity, we probably should have made room for ten more.
But you should go ahead and watch full episodes of Chappelle’s Show on SBS On Demand.