8. Old 97's, "Question" (2001)

In simple terms, with perfectly chosen details ("She woke from a dream/ Her head was on fire/ Why was he so nervous?"), Rhett Miller sketches a man proposing to a woman. Then, the kicker, which must, must, tug on even the crankiest heart: "Maybe tonight, I've got a question for you." ā€” Peter Smith

Drake, "Best I Ever Had" (2009)
Explore more ...