Known for his excellent taste in singer-songwriters (ex-wives Kate McGarrigle and Suzzy Roche) and his top-shelf DNA (kids Rufus and Martha Wainwright), Loudon Wainwright III is also one hell of a songsmith. With notes by pal Judd Apatow, this career retrospective is long on hilarious memoir, and lyrics about being a boozy, tragic pussy hound have gained depth in light of his family history. The bonus disc includes duets with his exes - celebrations and laments that epitomize the juggling act he's kept up for an entire artistic life.

Listen to Loudon Wainwright's "Motel Blues":

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“The A Team”

This debut track from the then-20-year-old British singer-songwriter has a dark story behind it. Sheeran says he culls songwriting inspiration from "viewing other people's situations," which, for the heroine in "The A Team," involves drug addiction and prostitution that began as a teen. Sheeran paints the woman's trials with haunting imagery such as "But lately her face seems/Slowly sinking, wasting/Crumbling like pastries." "I did a gig at a homeless shelter, [and the song] is about one of the women there. It's her story," he said.