Produced by Don Costa and Sonny Burke, My Way was released in March 1969 and features an eclectic collection of contemporary pop songs, including Simon and Garfunkel's - "Mrs. Robinson," The Beatles - "Yesterday," Ray Charles - "Hallelujah I Love Her So," and the iconic title track, "My Way," which would become his career theme song. The song occupies a special place in popular music, influencing generations of musicians, including Elvis Presley who conspicuously recorded his own version.

Famous Sinatraphile Bono, who contributes the My Way 40th Anniversary Edition liner notes, wrote of the song, "..[it's] a boast - more kiss-off than send-off - embodying all the machismo a man can muster about the mistakes he's made on the way from here to everywhere." Also included are two unreleased tracks: Stevie Wonder's classic "For Once In My Life," recorded on August 13, 1969 for the Sinatra television special, and a live version of "My Way," recorded on October 24, 1987, at Reunion Arena in Dallas.