While “That’s Life” was first recorded by Marion Montgomery, the song came to the attention of Frank Sinatra when he heard O.C. Smith’s chart-climbing cover in his car in 1965. He stopped the car, called his daughter Nancy and told her to find the publisher of the song because he wanted to record it; she did. Sinatra first performed the song on his television special A Man and His Music – Part II in 1966, with an arrangement by Nelson Riddle.
The recorded version, made after the taping to the TV Special, was arranged and conducted by Ernie Freeman and produced by Jimmy Bowen. The trio had previously worked together earlier in 1966 on “Strangers in the Night”, which got Sinatra the Grammy Award for Best Male Vocal. For “That’s Life”, the background singers were the vocal contractor and singer B.J. Baker, along with Gwen Johnson and Jackie Ward. 40 first-chair musicians were also assembled for Sinatra’s recording including Glen Campbell and many of the members of the Wrecking Crew. Sinatra took two passes at the song. He ended the first take with, “Oh yeah.” Bowen asked him to perform it again, which annoyed ‘one take’ Sinatra – resulting in the biting performance Bowen was looking for – which Sinatra tagged with the defiant, “My, My.” LA session player Mike Melvoin performed the Hammond organ solo on the recording.
Bowen’s vision for the rest of the album was to mirror “That’s Life” onto the other songs so they all sounded similar, rather than fill it with what he viewed as typical Sinatra-style songs. This was as a result of his work on the Strangers in the Night album, where Bowen felt that the titular single did not match the rest of the album, which was more of a classic Sinatra sound. So for the That’s Life album, the other album tracks had similar brass accompaniments.
Both the album and the song proved major successes for Sinatra. The song was a number-four hit on the US Billboard Hot 100 chart and reached number one on the Easy Listening chart for three weeks in December 1966/January 1967. In Canada, the song reached number three. Sinatra’s cover of “That’s Life” was later used in the 1993 film A Bronx Tale alongside his recording of “Same Old Song and Dance”. It was also featured in the 2004 video game Tony Hawk’s Underground 2. The song was also in the 1988 film License to Drive, the 2019 film Joker, and during the final scene of the final episode of the sixth season of the NBC television comedy series Brooklyn Nine-Nine.
Usually after home losses, the Vegas Golden Knights play the Sinatra version at T-Mobile Arena.