Remember When a Glam Metal Icon Covered a Frank Sinatra Song With Surprising Success in 1986?

In 1966, Frank Sinatra released “That’s Life”. The song, written by  Dean Kay and Kelly Gordon, was first recorded by Marion Montgomery in 1963. But it wasn’t until Sinatra released “That’s Life” that the song became a big hit. “That’s Life” is the title track of a record also released in 1966.

Sinatra’s version of “That’s Life” stayed at the top of the charts for three weeks. It’s unlikely Sinatra ever imagined that, 20 years later, a rockstar would put his own spin on the nostalgic tune. However, that’s exactly what happened. In 1986, David Lee Roth recorded “That’s Life”. Roth’s cover of “That’s Life” is part of Eat ‘Em And Smile, Roth’s first solo album after leaving Van Halen.

Roth may have never recorded “That’s Life”, or any of the songs on Eat ‘Em And Smile, if not for releasing Crazy From The Heat. Crazy From The Heat is Roth’s first solo EP, out in 1985. Crazy From The Heat has just four songs. They were all covers of classic songs that were a definite departure from the music of Van Halen, including “California Girls”. When Roth saw how successful the EP became, he chose to leave Van Halen and pursue a solo career.

Roth released “That’s Life” as a single, although it did not do well as a single for him. However, Roth did have two hit singles from Eat ‘Em And Smile, with both “Yankee Rose” and “Goin’ Crazy”.

The Story Behind “That’s Life” by Frank Sinatra

Montgomery is the first artist to record “That’s Life”, but that isn’t how the song was heard by Sinatra. Instead, in 1967, O.C. Smith released “That’s Life” as his first single. Smith’s version did not chart, but it did get heard by Sinatra, who decided to record the song himself.

The song was historic for Sinatra, but not necessarily in a good way. Sinatra notoriously recorded most of his songs in one take, but not “That’s Life”. 

“[I] was sitting five feet away from Frank Sinatra and producer Jimmy Bowen when they listened to the playback of the first take,” Kay recalled to Songfacts. “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,” he added, “that his displeasure is manifested in the extra bite in his performance, which is exactly what Bowen was looking for.”

Two years after Roth released “That’s Life”, he had his first and only No. 1 single as a solo artist, with “Just Like Paradise”. After Sinatra released “That’s Life”, he returned with “Somethin’ Stupid”. A duet with his daughter, Nancy Sinatra, “Somethin’ Stupid” became Sinatra’s last No. 1 hit.

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