The album is mainly a collection of then-contemporary pop songs, such as Simon and Garfunkel's "Mrs. Robinson", and The Beatles' "Yesterday", French songs such as "If You Go Away", and the anthemic title song "My Way", which effectively became Sinatra's theme song in this stage of his career.

On December 30, 1968 in Los Angeles, a few hours before going to celebrate the New Year 1969, at the Sands Casino from Las Vegas, My Way was recorded and mixed at EastWest Studios, then called Western Recorders.

"My Way" is a song popularized in 1969 by Frank Sinatra set to the music of the French song "Comme d'habitude" composed by Jacques Revaux with lyrics by Gilles Thibaut and Claude François and first performed in 1967 by Claude François. 

The English lyrics of the song were written by Paul Anka and are unrelated to the original French song. 

The song was a success for a variety of performers including, Sinatra, Elvis Presley, and Sid Vicious. Sinatra's version of "My Way" spent 75 weeks in the UK Top 40, which is 4th place of all time.

"My Way" was released in early 1969 on the My Way LP and as a single. It reached No. 27 on the Billboard Hot 100 chart and No. 2 on the Easy Listening chart in the US. In the UK, the single achieved a still unmatched record, becoming the recording with the most weeks inside the Top 40, spending 75 weeks from April 1969 to September 1971. It spent a further 49 weeks in the Top 75 but never bettered the No. 5 slot achieved upon its first chart run.

Billboard said that the "driving, lush and commercial Don Costa arrangement and production is an added plus to one of Sinatra's finest performances." Cash Box said that "The powerful material is matched by a splendidly moving performance which is certain to win rave comments from programmers with teen and adult audiences."

In 2000, the 1969 release of "My Way" by Frank Sinatra on Reprise Records was inducted into the Grammy Hall of Fame.