Pink Houses by John Mellencamp is featured in Laryngitis, the eighteenth episode of Season One. It is sung by Kurt while trying to act "masculine" in order to further connect with his father, whom he feels is slipping away from him.
In an effort to connect with his dad, Kurt takes interest in things his dad is interested in. This includes singing one of his father's favorite songs by one of his favorite artists.
Kurt at first believes the song to be about "bold interior design." After he performs this, Mr. Schue criticizes it because it isn't the right song that explains who Kurt really is inside. Brittany, however, enjoys it, leading her to make a proposition with Kurt afterwards.
There's a black man with a black cat
Livin' in a black neighborhood
He's got an interstate runnin' through his front yard
You know he thinks that he's got it so good
And there's a woman in the kitchen
Cleanin' up the evenin' slop
And he looks at her and says, "Hey darlin',
I can remember when you could stop a clock."
Oh but ain't that America for you and me
Ain't that America somethin' to see, baby
Ain't that America home of the free
Little pink houses for you and me
Oh, baby, for you and me!
After Kurt sings Pink Houses, Brittany walks up to him and says he's basically the only guy in school she hasn't made out with, however, in season two in Duets when trying to get Artie to be her duet partner he says she's never even talked to him (she concluded she thought he was a robot), but that would mean that her statement being that Kurt was basically the only guy was false because she hadn't made out with Artie either let alone talk to him. But the statement Brittany made was actually true in her own mind - because she said she made out with all the GUYS in school. And because she thought Artie was a robot, she did not include him in the list of the guys in school.