"Goodbye Cruel World" is a song written by Gloria Shayne Baker, who also wrote the well-known Christmas carol, "Do You Hear What I Hear?" and several songs for singer Lesley Gore. The most famous recording of this song is by James Darren. With its release as a single in 1961, Darren scored his first top ten hit on the Billboard Hot 100, at number three. It would prove the biggest hit of his career on this chart, as well as on the UK Singles Chart (no. 28).

Darren, playing pop idol "Kip Dennis", performed the song on a late 1961 episode of The Donna Reed Show. (He had previously played a different character in a 1959 episode of the sitcom). The song's lyrics were changed to "join the Army" instead of "join the circus" to reflect his character's reason to exit the show as Shelley Fabare's "love interest" ala Elvis' zeitgeist Army stint.

The song was also used in a film on Pop Art directed by Ken Russell for the BBC TV series Monitor which was aired in March 1962; its context here was the escape from the dying culture of the British Empire.

According to disc jockeys at the time the song was released, the calliope-like riff used in the song based on the "Entrance of the Gladiators" theme, was a synthesized recording of a woman's voice rather than a musical instrument.

The song is about a man whose heart was broken by a "mean fickle woman", and his plan to join the circus as a brokenhearted clown. He does not mind being shot out of a cannon, and plans to tell the world that this she "made a crying clown" out of him.

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Wikipedia