5 of the Most Memorable Frank Sinatra Songs

Frank Sinatra is one of the most legendary singers in American history. His voice was incomparable, and he was not only talented as a singer but also as an actor – he even won an Oscar. Up until his death in 1998, Sinatra performed and drew crowds as one of most beloved entertainer’s of his time, including the iconic “Rat Pack” years. From World War II up until the late ’90s, you could practically hear Frank Sinatra songs everywhere you went. When people think of Frank Sinatra, they think of big band swing music, his effortlessly cool style, his performances as a singer and actor, and these items are all ingrained in the minds of the public, making him one of the most iconic celebrities of all time. 

While Sinatra sang so many memorable songs throughout his career, some that just display the epitome of who he was and best reflected his style of music. These are the five most remarkable Sinatra songs of all time that undoubtedly mark the successes of his career as a singer.

“New York, New York”

Who could forget the opening line of “I’m spreading the news…?” Sometimes considered the National Anthem of New York City by some people, this remarkable song became a Sinatra classic when he recorded the song, originally sang by Liza Minelli, for his album Trilogy: Past Present Future.

“My Way”

Considered Sintra’s biggest hit, the song was Sinatra’s title single for his latest album in 1969. It broke record in the U.K. by spending 75 weeks in the pop Top 40 from April 1969 through September 1971. Reportedly, singer-songwriter Paul Anka called up Sinatra at 5 A.M. and told him he had “something special” for him when he rewrote the song, originally in French.

“Somethin’ Stupid”

Featuring his daughter Nancy Sinatra, the father-daughter duet was the first of its kind to ever reach the #1 spot on the U.S. pop chart and even earned a Grammy Award nomination for Record of the Year. The pair turned a folk song into a pop sensation that spent four weeks at the top of the pop chart and #1 on the easy listening chart.

“Fly Me to the Moon”

Originally titled “In Other Words” and sung by Kaye Ballard, Sinatra reworked the song in his own famous style in 1964 as “Fly Me to the Moon” for the joint album with Count Basie It Might As Well Be Swing. The song became associated with NASA’s Apollo space program and was played on the Apollo 10 mission that literally flew to the moon (or rather, orbited). The song was played again as the first music ever to be played on the surface of the moon when Buzz Aldrin played it on a cassette player after stepping on the moon in the Apollo 11 mission. These events make this song quite a part of American and space history. 

“That’s Life”

First recorded by Marion Montgomery, and later by O.C. Smith, which caught the attention of Sinatra, he sang the song as part of 1966 TV special called A Man and His Music – Part II. The song was then re-recorded by Sinatra and released as a single and was used as the title song for an album and reached the #4 spot on the Billboard Hot 100 and the top of the easy listening chart.