The original context of the song, in the film Robin and the 7 Hoods, is the mob boss Robbo (Sinatra) having just been acquitted of murdering the sheriff, a crime for which he had been framed.

[2] Popularized by Sinatra, "My Kind of Town" was originally recorded on April 8, 1964, in Los Angeles, California.

The music is written in the key of A-flat, in 2/2 meter (known as cut time) with an allegro tempo.

[13] The song also appears on The Ultimate Rat Pack Collection: Live & Swingin', a 2003 DVD and CD release of the 1965 "Frank Sinatra Spectacular" benefit concert.

[4] Other credited vocalists on the score were Dean Martin, Bing Crosby, and Sammy Davis Jr.

[43] Frank Sinatra sings a popular version of "Chicago (That Toddlin' Town)" that charted and was the B-side to the 1957 Academy Award for Best Original Song winner, "All the Way".

On Ruby Braff's 1981 tribute album, Very Sinatra he does a medley called "New York, New York/My Kind Of Town (Chicago Is)".

[45] Jack Jones, who won two Grammy Awards in the 1960s and charted dozens of songs including the theme from The Love Boat, recorded an album entitled My Kind of Town with a title track by the same name.

[46] Among the other artists who have recorded versions of the song are Ray Anthony, Count Basie (twice), Ray Conniff, Marvin Gaye, Jackie Gleason, Jeff Harnar, Biréli Lagrène, Steve Lawrence, Julie London, Frankie Randall (several times.