In Pick Five, great artists pick five cover songs that matter to them.

In 1991, Townes Van Zandt wrote the following: “Anytime anyone asks me who my favorite music writers are, I say Mozart, Lightnin’ Hopkins, Bob Dylan, and Dave Olney. Dave Olney is one of the best songwriters I’ve ever heard — and that’s true. I mean that from my heart.”
Twenty-seven years later, Townes is gone, but Olney keeps on keepin’ on. He may not have become a household name in that time, but his reputation among his peers has only grown. Emmylou Harris has sung three of his songs. Linda Ronstadt tackled a pair herself. When Steve Earle covered Olney’s “Saturday Night and Sunday Morning,” he noted it took him four or five years of playing the song before he realized it was “so perfectly constructed that it doesn’t have a rhyme in it.” He added that Olney was “one of the best songwriters in the world.”
Olney’s latest album, out this week, is This Side or the Other. It features nine new pieces of his own impeccable writing, plus a cover of the Zombie’s “She’s Not There”:
Given how often Olney’s own songs have been covered, we asked him to share five of his favorite cover songs. He’s too modest to pick any of his own compositions, but he does begin with a friend, and a fan.
Townes Van Zandt – Dead Flowers (Rolling Stones cover)
David says: “Featured at the end of The Big Lebowski. I think Townes would fit right in with The Stones.”
Tom Waits – Somewhere (Leonard Bernstein/Stephen Sondheaim cover)
David says: “The song is from West Side Story. Waits’ rough vocals gives the song such depth. Like, there’s a place even for ugly people.”
Alison Krauss – Baby Mine (Dumbo cover) cover)
David says: “If you are not moved by this song, you should visit a doctor immediately. Chances are, you’re dead.”
Jimmy LaFave – Red River Shore (Bob Dylan cover)
David says: “This song is about eight minutes long. If you don’t sing it with total commitment, nobody will listen past the first verse. Jimmy knocks it out of the park. I thought for years it was his song. I found out later Bob Dylan wrote it.”
Aretha Franklin – Bridge Over Troubled Water (Simon & Garfunkel cover)
David says: “The interplay between Aretha and the background singers is beautiful. The last verse always sounded awkward to me in Simon and Garfunkel’s version. Aretha makes it work.”
Preorder David Olney’s ‘This Side or The Other’ (out Friday) at his website.