The first artist to record for the Beatles' label Apple (Apple #1),in 1968, even before the Fab Four, was none other than. . .well, take a listen
It came about this way, as described elsewhere on the net: "Ringo Starr's wife, Maureen, had a birthday coming up and someone at Apple Records thought it would be great to work up a version of "The Lady Is A Tramp" to play at her birthday party. One thing led to another and songwriter Sammy Cahn agreed to rewrite the words to the song ("Maureen Is A Champ"), then talked FRANK SINATRA into singing it. Sinatra recorded the song with his longtime accompanist Bill Miller, shipped the tape to London, where it was pressed onto Apple #1. One copy of the record was made and given to Maureen Starr, and the stamping mold was then destroyed afterward."
That's the official version. However, one suspects that Sinatra's gesture might not have been exactly one of altruism, friendship, or love of the Beatles, but rather the part of some larger corporate scheme. Perhaps, the Beatles had not yet signed on the dotted line to have parent company EMI distribute Apple, and since Sinatra was still a stockholder in the Warner-Reprise combine. . .. Or else. . .? Even the Chairman, who despised rock, must've had his price; and George Harrison's "Something," which Sinatra embarrassingly recorded, doesn't really qualify as rock, per se.
Maureen died in 1994 and according to a couple of net sites that I went to, no one seems to know whatever happened to the 45 which no doubt today would fetch a pretty penny at auction. Not since the Dean Benedetti Charlie Parker tapes!