"Cogs in Motion" definitely counts. It's like something out of a factory scene in a silent black-and-white 1930's cartoon, which makes it awesome. (It does play in a factory (of the 30s themed Toy Mafia).)
Season 2 has a time travel episode. Back to the 80s!
According to composer Jared Emerson-Johnson, each of the Telltale episode contains as much music as an average 30-hour console title. So these games are really concentrated with music of awesome.
If an area is reused, the music is reused too - and a lot of areas are reused in Season 1. Even then, some of the tracks are remixed, so to speak, in later seasons. Sybil's office in particular has extra musical accompaniment in Season 2 that wasn't in Season 1.