Sinatra won the Golden Globe Award for Best Actor - Motion Picture Musical or Comedy for his role as the wise-cracking, hard-bitten Joey Evans.

Nelson Riddle handled the musical arrangements for the Rodgers and Hart standards "The Lady Is a Tramp", "I Didn't Know What Time It Was", "I Could Write a Book", and "There's a Small Hotel".

[3] Joey Evans, a womanizing nightclub singer, is thrown out of town for romancing the mayor's underage daughter, and forced to board a train to San Francisco.

Later that night, Ned lands another gig at a children's charity event in Nob Hill, and brings Joey and Linda English, a naïve chorus girl, along.

The event falls short of its intended fundraising goal, in which Joey has the attendees raise thousands to have Vera Prentice-Simpson, a widowed socialite and former striptease dancer, perform a routine.

Note: Robert Reed made his unbilled feature film debut as the boy friend sitting at the front couple's table while Sinatra sang "I Didn't Know What Time It Was."

According to Dorothy Kingsley, who wrote the script, the film was meant to star Kirk Douglas and be directed by George Cukor.

The plot of the film drops a blackmail attempt, and two roles prominent on stage were changed: Melba (a reporter) was cut, and Gladys became a minor character.

Also in the film, Vera Prentice-Simpson is a wealthy widow and former stripper (billed as Vanessa the Undresser) and thus gets to sing the song "Zip".

(Since that number requires an authentic burlesque drummer to mime the bumps and grinds, the extra playing the drums is disconcertingly swapped with a professional session musician Jimmy Fernandes in a jump cut).

[6] The music was supervised by Morris Stoloff and adapted by George Duning and Riddle, with Arthur Morton contributing orchestrations.

"The Lady Is a Tramp" is a mono-only outtake from Sinatra's 1957 album A Swingin' Affair!,[7] while three others ("There's a Small Hotel", "Bewitched", and "I Could Write a Book") were recorded in mono only at Capitol Studios.

Dorothy Kingsley's screenplay, from John O'Hara's book, is skillful rewriting, with colorful characters and solid story built around the Richard Rodgers and Lorenz Hart songs.

"[12] The New York Times stated, "This is largely Mr. Sinatra's show...he projects a distinctly bouncy likeable personality into an unusual role.

And his rendition of the top tunes, notably "The Lady Is a Tramp" and "Small Hotel," gives added lustre to these indestructible standards.