Chicago (That Toddlin' Town) "Chicago " is a popular song written by Fred Fisher and published in 1922 . The original sheet music variously spelled the title "Todd'ling" or "Toddling." The song has been recorded by many artists, but the best-known version is by Frank Sinatra . The song alludes to the city's colorful past, feigning "... the surprise of my life / I saw a man dancing with his own wife", mentioning evangelist Billy Sunday as having not been able to "shut down" the city, and State Street where "they do things they don't do on Broadway". The song made a minor appearance on the U.S. pop charts, reaching #84 in the fall of 1957 . It was the first of two charting songs about Chicago recorded by Sinatra. The other was "My Kind of Town" from 1964, which reached U.S. #110.Chart history Film appearances 1939 - featured in H.C. Potter's 1939 film, The Story of Vernon and Irene Castle , starring Ginger Rogers and Fred Astaire . 1942 - the song was featured in the opening and closing credits of the 1942 movie Roxie Hart starring Ginger Rogers and Adolphe Menjou . 1949 - included in the fictionalized biography of Fred Fisher, Oh, You Beautiful Doll . 1952 - used in the 1952 film With a Song in My Heart . 1957 - performed by Frank Sinatra in a 1957 movie in which he starred, The Joker Is Wild . His separately-recorded rendition is the only charting version of the song. 1974 - appears in the film Harry and Tonto .Recorded versions Synco Jazz Band Jamey Aebersold Ann-Margret George Barnes Luis Barreiro Count Basie Laura Benanti - The Playboy Club Tony Bennett Pierre Blanchard Claude Bolling Boston Pops Orchestra James Brown Dave Brubeck John Bunch Benny Carter Chicago - Rosemary Clooney Bing Crosby for his 1957 album New Tricks . Graham Dalby & the Grahamophones Sammy Davis Jr. Jimmy Dorsey Tommy Dorsey John Eaton Duke Ellington Bob Florence Pete Fountain Sergio Franchi on his 1964 RCA single Bud Freeman Jackie and Roy Judy Garland on her double LP Judy at Carnegie Hall and the studio album Judy in London The Georgians Harry Goldson Nat Gonella & His Georgians Benny Goodman Stéphane Grappelli Coleman Hawkins Earl Hines Mimi Hines Franz Jackson Milt Jackson Jazzbo's Carolina Serenaders Jive Bunny & the Mastermixers Al Jolson Greetje Kauffeld François Laudet Lead Belly Joe Lovano Billy May Dudley Moore Jaye P. Morgan Jack Mudurian Bill O'Connell Anita O'Day Original Piano Trio Oscar Peterson Louis Prima Quintet of the Hot Club of France Lou Rawls Django Reinhardt Buddy Rich Tony Sandler Bob Scobey The Sentimental Strings John Serry Sr. and his ensemble. Screeching Weasel Ray Sherman Victor Silvester Frank Sinatra - Come Fly with Me Muggsy Spanier The Starlite Orchestra Wally Stott and his Orchestra Barbara Sutton Curtis George Holmes Tate Gary Tesca Rufus Wainwright - Rufus Does Judy at Carnegie Hall Paul Whiteman and His Orchestra World's Greatest Jazz Band Wurlitzer Band Organ Wurlitzer Model 165 Band Organ Penn Glee Club George Scott Wood's Six SwingersLive covers Green Day during a concert at Chicago's United Center on July 13, 2009 Sergio Franchi recorded this song in Italian during his concert in 1965 for RCA Victor , Live at The Coconut Grove CM Punk at the end of the 27 June 2011 edition of Monday Night Raw
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