- The laundromat sketch. Right from the start, we have the laundromat owner lamenting that more people are frequenting the more hip and happenin' barbershop across the street... and then the one guy who's still frequenting the laundromat ends up crossing over. And then we get the cameo from Billy Dee Williams. That's not even the last of it - they twist the knife further with the barbershop starting its own laundry service. And then they shove the knife home with a Wham Shot of the laundromat wall. Billy Dee used to frequent the laundromat too.
- The end of the rap battle hype man one can count as this to some.
- The two Slap-Ass sketches count too, for taking something as mild as slapping a teammate's ass at a baseball game and treating it like a drug problem, playing it for laughs and for drama.
- The Wendell sketches (which are both hilarious and kind of sad). It's very clear that Wendell is deeply lonely and unhappy with himself and the way his life turned out.
"There you are, with your round body and your creepy-ass face! No more sweets for you, 'cause you're never gonna get laid if you keeps eatin' sweets! And another thing, all these toys and figurines you've got around the house? We're throwin' them in the trash, 'cause they're not real people, Stimpy! THEY'RE NOT REAL PEOPLE! SO STOP BEIN' SO LONELY! Stop...being...so lonely.
- His monologue from the Superman bed sketch stands out, where he's yelling at his "son" (a Stimpy plush doll), but is actually giving himself a "Reason You Suck" Speech.
- Even the sketch 'The Power of Wings' carries a hint of this. Wendell is finally allowed to live out his fantasy, being the hero of an epic fantasy adventure, and then just when he's about to get the girl... the budget runs out and he's back to being his miserable, lonely self.
- The mafia sketch, where Vinny mistakes his surprise party for an ambush, and shoots his friends and family dead.
- The "Pussy on the Chain Wax" sketch, which starts with a guy calling his friends out when they keep using fake slang and eventually escalates until the friend who came up with the saying reveals that he lost his job, his girlfriend left him, and that he was hoping to have a nice day with his friends to get his mind off of it. The sketch ends with the skeptical guy happily repeating the phrase with them.
- The School Bully sketch, which wastes no time deconstructing the behavior of kids who pick on others.
- The Negrotown sketch, where the characters don't get a happy ending. Specifically, the sketch is about a place where black people can live without having to deal with hatred and persecution. Turns out it doesn't actually exist, and the sketch ends with the main character, an innocent man, being carted off to jail by a racist cop.
- "These Nuts", which takes an annoying joke and turns it into a tragic story about a man trying to deal with his dead family.
- The emotional abuse Meegan puts Andre through can be hard to watch, and the sketches involving the two of them get progressively darker as the relationship gets more toxic.
Tear Jerker / Key & Peele