That's Life by Frank Sinatra

Album: That's Life (1966)

Charted: 44 4

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This very optimistic song was written by Dean Kay and Kelly Gordon. Kay became a successful music publisher, and Gordon made a mark as a producer. Sinatra had a lot of ups and downs in his personal and professional life, and this song was a great showcase for his spirit and resilience. The phrase "That's Life" is often used to convey disappointment, but here Sinatra sees all the good things that life brings.
Sinatra sang this with a scowl in his voice that was out of character, but exactly what the song needed. A story circulated that producer Jimmy Bowen told Sinatra, after the recording session, to get out of his car and back in the studio to re-record the vocal, which made Frank very angry and resulted in his edgy vocal. The song's co-writer, Dean Kay, told Songfacts the real story.

"I'm the writer of 'That's Life' and 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. 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. The 'My, My' ending was directed at Bowen in a 'how do you like that, Charlie' sort of way. The first take ended with, 'Oh, yeah.'

'My, My' is the catch phrase that has been associated with the song - and Sinatra - from that night forward. Frank Sinatra recorded my song when I was 26. I have been, and will always be, grateful for his magnificent recording that changed my life forever. (more at deankay.com)
This was one of two Sinatra songs - the other being "Strangers in the Night" - prominently featured in the '80s comedy License to Drive. Les (Corey Haim) takes his crush (Heather Graham) out for a wild night in his grandpa's Cadillac, which has a Sinatra cassette stuck in the tape player. This song plays when Les and his friends frantically chase a drunk who steals the car for a joyride (and sings along to Sinatra's tune).
David Lee Roth brought this song back to the charts in 1986 when he released it on his first solo album, Eat 'Em and Smile. Released as a single, it went to #85 in America.
"That's Life" was first recorded by jazz vocalist Marion Montgomery in 1963. It was followed by O.C. Smith's version, which Sinatra chanced upon while driving when it came on the radio. Sinatra stopped the car, called his daughter Nancy and instructed her to find the publisher of the song because he wanted to record it.

Comments: 11

Daniel from Ireland I believe the song brings to light all the things we think about while we go through life, there are times when we want to roll ourselves up and die metaphorically. However, I believe the roller-coaster feeling from the song just shows how them feelings can change through time.
FI agree with Gregg, this isn't a feel good song but it sounds like it at first which is great. It's a song saying he is going to kill himself because life is s--t.
Gregg from Tokyo, JapanI'm confused why this is considered an optimisitc song when it ends with a suicide promise. That twist at the end would seem to turn the meaning of entire rest of the song from a song of optimism into a song of pessimism as in "I've tried and tried and nothing is working so if something doesn't change soon I'm going give up soon and just kill myself".
Barry from Sauquoit, NyOn December 10th 1966, "That's Life" by Frank Sinatra peaked at #1 (for 3 weeks) on the Cash Box Magazine Top R&B Singles chart...
On November 13th, 1966 it entered Billboard's Hot Top 100 chart; and on December 18th, 1966 it peaked at #4 (for 2 week) and spent 11 weeks on the Top 100...
And on Christmas Day 1966 it reached #1 (for 3 weeks) on Billboard's Adult Contemporary Tracks chart...
The song was from his album of the same name; the album peaked at #6 on Billboard's Top 200 Albums chart...
In 1986 David Lee Roth covered it; his version peaked at #85 on the Top 100...
May Mr. Sinatra R.I.P. (1915 - 1998).
Steve Dotstar from Los Angeles, Cahey, frank did a great verion of this on one of his 60s tv specials with riddle conducting and artie kane? on organ?
Erik from Los Angeles, CaMan, the first time I heard this, I felt like he was singing about the last little bit of my life: I was "ridin high in April, shot down in May," but with school ending in a couple weeks and the whole Summer to turn life around however I wanted, I knew I'd be "back on top in June."
John from Fort Worth, TxThis old man agrees with the first two posters, It's a great feel-good song that only Sinatra could do justice to.
John Martin, 46
Joshua from La Crosse, WiDavid Lee Roth covered this on his 1986 album Eat 'em And Smile. He did mangle some of the lyrics, which may explain why it never got very far on the charts.
Howard from St. Louis Park, MnThis was Frank Sinatra's first big hit after Strangers in the Night. It's a great song with the classic lyrics "I've been a puppet a pauper a pirate a poet a pawn and a king."
Dennis from Chicagoland Burrows, IlThis is a good one when your feeling in the sh*tter, or just in need of a reality check. Its a good montra to have handy.
Scott Recs from Toronto, CanadaThis puts it all in to proportion when I'm down. It's a great song.

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