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Frank Sinatra historically covered music written by many different artists, adding his twist to popular songs. However, there was one John Denver tune where Old Blue Eyes may have outdone the original.

‘Leaving on a Jet Plane’ Was Covered by Frank Sinatra in 1970

Frank Sinatra recorded his version of John Denver’s “Leaving on a Jet Plane” in 1970. It was released on his 1971 album Sinatra & Company. The original music and lyrics were written by the folk singer in 1966.

Denver’s version of the song was more folk-inspired than Sinatra’s bluesy version. There is also a distinct version in the delivery of the tune. One was sung by a young man in his early 20s and the other, a road-weary entertainer in his mid-50s.

Sinatra’s version of “Leaving on a Jet Plane” sounds like it was written for him. But as he sings each line of the lyrics, one can hear the years he spent away from family and friends.

Sinatra & Company was released at the start of Frank Sinatra’s two-year retirement from show business in 1971. It was cobbled together from unreleased Reprise material.

The entertainer was reportedly a big fan of Denver’s songwriting. In addition to “Jet Plane,” Sinatra recorded the Denver songs “My Sweet Lady,” “Like a Sad Song,” and “The Game is Over.”

Sinatra co-starred on Denver’s 1976 ABC-TV special, John Denver and Friends. Subsequently, John guested on Frank’s TV show, Sinatra and Friends.

What is ‘Leaving on a Jet Plane’ about?

John Denver would write lyrics and songs inspired by events occurring in his life. He used his time in new places or his longing for something different as inspiration for his lyrics. 

Denver wrote “Leaving On a Jet Plane” when he was on the road as a part of the Chad Mitchell Trio. He was longing for someone to love and how his constant traveling prevented him from achieving it. However, the tune was originally written in 1966 and called “Babe, I Hate to Go.”

“This is a very personal and very special song for me,” said Denver in a BBC radio interview, per American Songwriter. “It doesn’t conjure up Boeing 707s or 747s for me as much as it does the simple scenes of leaving. Bags packed and standing by the front door, taxi pulling up in the early morning hours, the sound of a door closing behind you, and the thought of leaving someone that you care for very much.”

He added, “It still strikes a lonely and anguished chord in me because the separation continues. Although not so long and not so often nowadays.”

The song was originally recorded by Peter, Paul, and Mary and released as a single in 1969. Denver subsequently recorded a version of it that same year.

Thus, the song became the trio’s only No. 1 on the Billboard Top 100 and their last hit record. It was the only version of “Leaving on a Jet Plane” that ever charted.

Who else has covered ‘Leaving on a Jet Plane?’

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Many popular artists covered this now-iconic John Denver classic. Thus, the beloved song has been interpreted in many ways by many different singers and musicians.

Some of the recorded versions of the folk song include those by Liz Callaway, Bobby Vinton, Brenda Lee, Eve 6, Andy Williams, Englebert Humperdink, Cass Elliot, Ray Stevens, My Morning Jacket, and even the cast of the television series Glee.

As posted on his official website, Denver shared his thoughts on how music unites everyone, no matter their social, political, or economic position. “Music does bring people together. It allows us to experience the same emotions. People everywhere are the same in heart and spirit. No matter what language we speak, what color we are, the form of our politics, or the expression of our love and our faith, music proves we are the same.”

John Denver died at age 53. He was killed in a single-fatality crash while piloting a recently purchased light plane in 1997. His remains were cremated, and his ashes were scattered in the Rocky Mountains. The singer-songwriter was awarded a posthumous Grammy award in 1997 for All Aboard!, an album that consisted of songs about trains.