Chicago Relocation

My Kind of Town: Robin Hood, Sinatra, and Dancing Cops

August 26, 2013

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John D’Ambrogio

Some comments from Baird & Warner‘s Elizabeth McGrath

I decided to look into why Sinatra is linked to arguably one of the most iconic songs about Chicago.  What exactly led the man of New York (slash New Jersey) to sing about our historic city in his classic, “My Kind of Town”? Turns out, this song was written for the film, Robin and the 7 Hoods, a musical staring Frank Sinatra, Dean Martin, Sammy Davis Jr. and Bing Crosby.

The musical is basically Robin Hood transferred to a 1930s Chicago mob.  Sinatra plays lead man Robbo a straight-laced mobster who starts charities for orphans and continuously refuses the advances of his fellow mobster’s daughter Marian’s evil ways.  Yes, this film exists and I’m not sure how I’ve gone this long without seeing it.

“My Kind of Town” debuts after Robbo (Sinatra) breaks free from prison and joins the crowd waiting for him outside. I’ve posted the clip below.  Make sure to note the New Orleans horn band and dancing cops as everyone rejoices that their savior Frank has been freed. It’s corny, it’s catchy and it was up for an Oscar but lost to Dick Van Dyke’s “Chim Chim Chr-ee” in Disney’s Mary Poppins.

Personally, I’ve always loved this song.  It embodies Chicago perfectly.  Chicago’s the glamour of the Wrigley Building, the reality of the union stock yards, and the Midwestern hospitality of people smiling at you.

If you’re ever lucky enough to cruise across Lake Michigan or down the Chicago River, play this song and you’ll understand exactly how great and magical the city of big shoulders can be.  Is that corny?  Absolutely.  But truly what’s wrong with things being a little corny every now and again?


Clip from TCM’s archives