It's usually the songs I like but don't quite know. So put them on a tape and play them in the car over and over and over until I could sing them in my sleep.Years later, when I hear one of these, it reminds me of the time when I was fanatical about that particular tune and it can take me back to that place.
Examples:
the entire Joni Mitchell album "Blue"
the entire Elvis Costello album "Brutal Youth"
Bob Dylan's song that starts "oh my love she speaks like silence" ["Love Minus Zero/No Limit"]
Anything by Jeff Buckley
Edie Brickell singing "Billionaire"
Tim Finn's "Crescendo"Callie