Larry Wilmore is usually dead on about most things. His Nightly Show has been a refreshing addition to the late night landscape since it debuted in January. But on Monday night's show, when talking about Bruce Jenner's transition, he got nearly everything wrong.
The bit gets off to a bad start with Wilmore making the idea of transitioning a punny punchline. It's not the worst thing ever said, but maybe a bit insensitive. Nothing to freak out about just yet.
Then he becomes strangely fixated on talking about parts — how Jenner could be a woman despite having man-parts, and how confusing it was compared to "back in the day."
It's possible Wilmore was trying to lampoon those who would ask such stupid questions, but there aren't any knowing winks in his line deliveries. He just feigns confusion, and none of his assumptions are so egregious (in the Stephen Colbert vein of exaggeration) as to only be taken as jokes. The way he delivers it, he makes Jenner and the transition the joke, not his own cluelessness.
The confusion hit almost every nerve possible. Why was Jenner married to women? Is he gay? Why does he still have a penis? It's all so confusing to Wilmore, and it's hurting him to think about.
The piece just seemed like a bad idea, front to back, and Wilmore leaves no stone unturned in his efforts to be as tone-deaf as possible. He even takes the laziest possible shot at Kanye West in light of his support of Jenner when talking to Kim Kardashian.
But the segment's worst moments come after he brings out Pinocchio as a special guest. You know, because Pinocchio also transitioned. It was exactly as stupid as it sounds.
The choice to include Pinocchio didn't add anything, and in fact, it reduced the idea of transitioning to a comparison to a puppet character. It's a gross comparison, and it's surprising no one in the writers' room thought better of it.
The writers on these teams are incredibly smart. They know how to do smart satire, and if they were trying to make a smart joke, it would have been much clearer. This was just a bad idea poorly executed. It's not the end of the world for The Nightly Show, and his promised piece on the situation in Baltimore on Tuesday night's show should be better.
Wilmore is a brilliant voice, but next time he tries to make jokes about something slightly outside his lane, he should make sure any cluelessness is his character's, not his own.
Watch the full clip below.