It was originally part of the musical score for Robin and the 7 Hoods, a 1964 musical film starring several members of the Rat Pack. It was nominated for the 1964 Academy Award for Best Original Song but lost to "Chim Chim Cher-ee" from Mary Poppins. Although the song predated the Grammy Award Best Original Song for a Motion Picture category, the entire score was nominated for the 1964 Grammy Award in the category Best Original Score Written for A Motion Picture, but it lost to the eponymously titled Mary Poppins score.
Frank Sinatra recorded several versions which have appeared on many of his albums. Also, many artists have performed the song as a tribute to Sinatra in posthumous tribute albums. In addition, the song had been recorded by many other artists prior to Sinatra's death. The lyrics, which praise the city of Chicago for its people and institutions, repeat the phrase My Kind of Town several times, usually in a line that says "My kind of town, Chicago is".
Now this could only happen to a guy like me And only happen in a town like this So may I say to each of you most gratef'lly As I throw each one of you a kiss
This is my kind of town, Chicago is My kind of town, Chicago is My kind of people, too People who smile at you
And each time I roam, Chicago is Calling me home, Chicago is Why I just grin like a clown.* (It makes me jump up and down) It's my kind of town (Every bit of it is) My kind of town, Chicago is My kind of town, Chicago is My kind of razzmatazz And it has all that jazz
And each time I leave, Chicago is Tuggin' my sleeve, Chicago is. (Grabbin' my sleeve, Chicago is) The Wrigley Building, Chicago is The Union Stockyard, Chicago is. (The Chicago Cubbies, Chicago is) One town that won't let you down It's my kind of town