About the song

If you are a fan of Frank Sinatra, you probably know his hit song “That’s Life”. But do you know the history behind this uplifting anthem of resilience and optimism? In this blog post, we will explore how Sinatra came to record this song, who wrote it, and what it means to him and his listeners.

“That’s Life” was written by Dean Kay and Kelly Gordon in 1963, and first recorded by Marion Montgomery, a British singer who was discovered by Peggy Lee. However, the song did not chart and remained obscure until 1965, when O.C. Smith, a former jazz vocalist for Count Basie, released a cover version that reached #25 on the Billboard Hot 100.

Sinatra heard Smith’s version on the radio while driving in his car, and was immediately captivated by the song. He called his daughter Nancy and asked her to find the publisher of the song, because he wanted to record it himself. He got his chance in 1966, when he worked with producer Jimmy Bowen and arranger Ernie Freeman on a new album titled That’s Life.

On July 25, 1966, Sinatra recorded “That’s Life” at United Recording in Hollywood, with a 40-piece orchestra that included Glen Campbell and members of the Wrecking Crew. He also had three background singers: B.J. Baker, Gwen Johnson and Jackie Ward. Sinatra was famous for doing almost everything in one take, but Bowen asked him to do a second pass at the song, hoping to get more bite and emotion in his performance. Sinatra was not happy to do it again, but he complied. His displeasure can be heard in his voice, especially in the final “My, my” phrase, which he directed at Bowen as a challenge.

The second take was the one that was released as a single in November 1966, along with “The September of My Years” as the B-side. The song proved to be a huge success for Sinatra, reaching #4 on the Billboard Hot 100 and #1 on the Easy Listening chart. It also earned him a Grammy nomination for Best Male Vocal Performance.

The song resonated with Sinatra and his fans because it reflected his own life story of ups and downs, failures and comebacks. He had faced many challenges in his career and personal life, such as losing his voice in the early 1950s, being dropped by Columbia Records, divorcing Ava Gardner, being snubbed by the Academy Awards, and being overshadowed by the British Invasion. But he always bounced back with determination and confidence, reinventing himself as a mature and sophisticated artist who could appeal to different generations.

“That’s Life” also captured the spirit of the times, when America was going through social and political turmoil in the 1960s. The song offered a message of hope and perseverance to those who faced adversity or discrimination, such as civil rights activists, anti-war protesters, or immigrants. The song also appealed to people from different backgrounds and walks of life, who could relate to its universal theme of overcoming obstacles and achieving one’s dreams.

Since its release, “That’s Life” has become one of Sinatra’s signature songs, and one of the most popular songs in the traditional pop genre. It has been covered by many artists over the years, such as Aretha Franklin, James Brown, Van Morrison, David Lee Roth, Michael Bublé, and Deana Martin (Sinatra’s goddaughter). It has also been featured in many films, TV shows, video games, and commercials, such as A Bronx Tale (1993), Casper (1995), Joker (2019), Tony Hawk’s Underground 2 (2004), Brooklyn Nine-Nine (2019), and Toyota (1996).

In this blog post, we have learned about the history of “That’s Life”, one of Frank Sinatra’s most iconic songs. We have seen how he discovered it, recorded it, and made it his own. We have also explored what it means to him and his listeners, and how it reflects his life story and the spirit of the times. We hope you enjoyed this introduction and found it informative. If you want to learn more about Frank Sinatra and his music, please visit our website or follow us on social media.