5. Reese De’What
In a 2019 Washington Post profile of Thompson, SNL executive producer Lorne Michaels called the actor “a master in [the] studio,” adding that “he knows the best way to do just about everything.” Thompson’s glue-guy gifts are on full display as De’What, a terrible husband who sets up clips of even more terrible television shows. His line readings are somehow surprising — no one else would deliver them the same way, and no one else could make a line as basic as “This is not why I’m here!” even remotely as funny. All hail the master.
4. Darnell Hayes
“Game show host” is a tough role on Saturday Night Live — the show uses the trope a lot to showcase questionable celebrity impressions, which leaves the host role a straight man at best. (See: Will Ferrell as Alex Trebek.) But on Black Jeopardy, Thompson takes center stage, elevating a tired archetype to something far more than the sum of its parts.
3. Steve Harvey
The internet’s been loving comparing Harvey to his daughter’s boyfriend, but the fact is that Kenan does a mean Steve — whether it’s on Family Feud, Who Wants to Be a Millionaire, or his very own show.
2. Jean K. Jean
A French Def Comedy Jam comic sounds like a tired premise. It is. But Keenan has so much fun mashing up the two sensibilities — “you ever be at a fete, and throw down some Gruyère? Turn around and you got vingt et cinq brothas holdin’ baguettes? Vingt de cinq!” — you can’t help but wish Jean had been around back when the HBO showcase was at its heyday.
1. Diondre Cole
As the host of What Up With That?, a late-night talk show that somehow never manages to get to the talking part, Thompson gives you absolutely everything he’s accumulated over his three decades in show business: impeccable timing, infectious energy, and the bemused chaos. Give this man his Emmy already!
Read more: The 6 Most Beloved Black Bostonians, Ranked