Some songs belong to their composers. Others belong to the person who sang them so definitively that no other version matters. Sinatra owned dozens of songs this way, not by writing them but by inhabiting them so completely that covering one required courage, a strong point of view, or at minimum a willingness to be compared unfavorably to the most confident voice in the history of American popular music. These are the artists who tried anyway, and what they found when they got there.
#1: Fly Me to the Moon — Bobby Womack
Written by Bart Howard in 1954 and made famous by Sinatra’s 1964 Capitol recording, the song found a completely different life when Womack slowed it down and draped it in soul. His 1969 version, the title track of his debut album, used horns and a rhythmic looseness that Sinatra’s big-band arrangement had never required. Where Sinatra swings with precision, Womack grooves with surrender, and the two versions illuminate entirely different emotional possibilities in the same song.
