With the release of his mammoth Triplicate album last week, Bob Dylan upped the number of Great American Songbook standards he’s covered to 52: 10 on 2015’s Shadows in the Night, 12 on last year’s Fallen Angels, 30 (30!) on Triplicate.
The original idea was that these would all be covers of songs Frank Sinatra once sang. Though Bob’s veered away from that some, Ol’ Blue Eyes still looms large. At their best, these songs embody Sinatra’s emotion and versatility as Dylan finds his own way in to a song. At their worse, they sound like Tony Bennett karaoke by someone who can’t sing.
So with so many of Dylan’s standards covers now out, we decided to rank all 52 songs. Some of Dylan’s finest-ever vocal performances are on these three albums. Also some that make Self Portrait look inspired. So let’s try to separate the wheat from the chaff, the curds from the whey, the In the Wee Small Hours of the Morning from the Sinatra Sings Great Songs from Great Britain.