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TL;DR:

  • Frank Sinatra’s “That’s Life” features a passive-aggressive lyrical addition from Ol’ Blue Eyes himself.
  • The co-writer of the song revealed what he thought of Sinatra’s cover of it.
  • “That’s Life” became the singer’s next-to-last top 10 single in the United States.
"That's Life" singer Frank Sinatra near a microphone
Frank Sinatra | William Gottlieb / Contributor

Frank Sinatra’s “That’s Life” became one of his most famous hit songs at a time when his style of music wasn’t dominant. Notably, he was annoyed when he recorded the uplifting song. Regardless, the track became part of a major comeback for Sinatra in 1966.

Frank Sinatra didn’t like having to record ‘That’s Life’ twice

Dean Kay co-wrote “That’s Life” with Kelly Gordon. Marion Montgomery recorded “That’s Life” in 1963, three years before Sinatra recorded the track in 1966.

During an interview with Songfacts, Kay discussed Sinatra’s recording of the tune. “[I] was sitting five feet away from Frank Sinatra and producer Jimmy Bowen when they listened to the playback of the first take,” he said. “It was then and there that Bowen asked Sinatra to take a second pass at the song.

“It’s a common myth that Bowen followed Sinatra to his car and made him come back into the studio for another take,” Kay added. “It is true that Sinatra, famous for doing almost everything he did in one take, was not happy to do it again. And, it is true that his displeasure is manifested in the extra bite in his performance, which is exactly what Bowen was looking for.” Sinatra’s aggressive vocal on the song was atypical for him.

Dean Kay had a strong reaction to Frank Sinatra’s cover of the song

Sinatra’s anger caused him to alter the lyrics of “That’s Life.” “The ‘My, my’ ending was directed at Bowen in a ‘How do you like that, Charlie’ sort of way,” Kay revealed. “The first take ended with, ‘Oh, yeah.'” From then on, “My, my” became Sinatra’s catchphrase.

Kay was 26 when Sinatra recorded “That’s Life.” Sinatra’s cover changed Kay’s life. The songwriter was grateful for the cover ever since, calling it “magnificent.”

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How ‘That’s Life’ became part of the singer’s 1960s comeback

1966 was a watershed year for Ol’ Blue Eyes. Earlier in the year, he released his pop smash “Strangers in the Night.” That ballad topped the Billboard Hot 100, becoming the singer’s first song since 1959’s “High Hopes” to spend more than 14 weeks on the chart.

“That’s Life” continued Sinatra’s string of hits, peaking at No. 4 and remaining on the chart for 11 weeks. The tune appeared on the album of the same name. That’s Life reached No. 6 on the Billboard 200 and lasted on the chart for 61 weeks.

Sinatra would hit No. 1 again in 1967 when he duetted with his daughter, Nancy, on the questionable track “Somethin’ Stupid.” He would never again release a top 10 hit. Regardless, it’s impressive that a traditional pop singer like him performed so well at a time when rock and pop-rock were the dominant musical forms. Songs from his 1966-1967 resurgence might be more famous today than anything he released during his peak in the 1940s and 1950s.

“That’s Life” is a great song even if Sinatra wasn’t keen on re-recording it.

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