Sinatra Rocks! Ol’ Blue Eyes' Best, Worst and Surreal Pop Covers
Late in his career, Frank Sinatra gave his own spin to a handful of rock hits. NBC/Getty

On two different levels, Bob Dylan's new Shadows in the Night, out this week, got us thinking about Frank Sinatra. First is the obvious reason: Although technically not a Sinatra "tribute," Dylan's record features his takes on songs Sinatra covered at various points in his life. Which, in turn, reminded us of the bizarre-world opposite scenario: the numerous times in his career that Sinatra waded into rock & roll.

In the Fifties, Sinatra made his contempt for rock more than obvious. In an article he wrote for a French magazine in 1957 — then widely reprinted in the U.S. — he decried what he called "the most brutal, ugly, degenerate, vicious form of expression it has been my displeasure to hear, and naturally I'm referring to the bulk of rock 'n' roll.... It fosters almost totally negative and destructive reactions in young people. It smells phony and false. It is sung, played and written for the most part by cretinous goons and by means of its almost imbecilic reiterations and sly, lewd — in plain fact, dirty — lyrics, and as I said before, it manages to be the martial music of every sideburned delinquent on the face of the earth." (Sinatra himself didn't exactly associate himself with the most wholesome characters on the planet, but that's another story.)

Roughly a decade later, with rock now commandeering the charts and crooners in danger of extinction, Sinatra softened a bit. From then through the early Eighties, he took periodic stabs at post-Elvis pop and rock songs: Paul Simon, Jim Croce, Neil Diamond, Jimmy Webb and Billy Joel all got the Ol' Blue Eyes treatment. Here are the surprising highlights — and surreal low points — of the times Sinatra tried to rock out.