History TearJerker / KeyAndPeele

** His monologue from the Superman bed sketch stands out, where he's yelling at his "son" (a [[WesternAnimation/TheRenAndStimpyShow Stimpy]] plush doll), but is actually giving himself a ReasonISuckSpeech.

** His monologue from the Superman bed sketch stands out, where he's yelling at his "son" (a [[WesternAnimation/TheRenAndStimpyShow Stimpy]] plush doll), but is actually giving himself a ReasonYouSuckSpeech.

* The Negrotown sketch, where the characters don't get a happy ending. Specifically, the sketch is about a [[{{Utopia}} place]] where black people can live [[SomeAnvilsNeedToBeDropped 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.

* Latiya in the "Fro Yo" sketch. She can't wait for her beloved boyfriend to come back from a year-long deployment. When he does, and sees how much she's blimped out in his absence, he [[ScrewThisImOuttaHere beats a hasty exit]]. She is devastated and oblivious to what caused him to abandon her.

* Latiya in the "=FroYo=" sketch. She can't wait for her beloved boyfriend to come back from a year-long deployment. When he does, and sees how much she's blimped out in his absence, he [[ScrewThisImOuttaHere beats a hasty exit]]. She is devastated and oblivious to what caused him to abandon her.

* Latiya in the "FroYo" sketch. She can't wait for her beloved boyfriend to come back from a year-long deployment. When he does, and sees how much she's blimped out in his absence, he [[ScrewThisImOuttaHere beats a hasty exit]]. She is devastated and oblivious to what caused him to abandon her.

* Noah is ''crushed'' that Michael Jackson passed away. Naturally, this is the punchline of the sketch, but Key sells it so well that you feel ''so'' bad for him.

* The emotional abuse Meegan puts Andre through can be hard to watch, and the sketches involving the two of them get progressively [[DarkerAndEdgier darker]] as the relationship gets more toxic.

* 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 WhamShot of the laundromat wall. [[spoiler:Billy Dee used to frequent the laundromat too.]]

* 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). Its very clear that Wendell is deeply lonely and unhappy with himself and the way his life turned out.

* The emotional abuse Meegan puts Andre through can be hard to watch, and the sketches involving the two of them get progressively [[DarkerAndEdgier darker]] as the relationship gets more toxic.
* The one where Key and Peele are chained up in the ''SAW'' bathroom. And the clown holding them is driven insane by the fact they are always so possitive.
-->YOUR MAKING ME CRAZY!!

-->:YOUR MAKING ME CRAZY!!

* The emotional abuse Meegan puts Andre through can be hard to watch, and the sketches involving the two of them get progressively [[DarkerAndEdgier darker]] as the relationship gets more toxic.

* 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 [[spoiler: 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 [[SugarWiki/HeartwarmingMoments happily repeating the phrase with his other friends]]]].

* 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 [[spoiler: 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 [[CrowningMomentOfHeartwarming happily repeating the phrase with his other friends]]]].