![]() ![]() You can still tour or see a show at many of the performance venues where Sinatra took the stage, but why not toast the singer's 100th birthday on December 12 from one of his favorite watering holes? Each of these bars and restaurants was frequented by Sinatra and his cronies, and together they make up a delicious tour of Frank’s Chicago. If you’re going to raise a toast to Ol' Blue Eyes, consider doing it with a Jack on the rocks. When the mafia came under investigation during JFK’s term, Sinatra paid the price-by playing eight consecutive days of forced performances with the Rat Pack at mob boss Sam Giancana’s night club in the Chicago suburbs. In 1960, he allegedly helped Chicago mobsters buy votes for the John F. ![]() The song also included appearances from Clint Eastwood. Even his love affairs reflected his love of the city: When Sinatra married Barbara Blakeley, he made sure to have his wedding reception at the Italian Village.īut the crooner of songs like “Chicago” and “My Kind of Town” was also part of the city’s dark side. Bar Room Buddies was the 29 song in 1980 in the Country charts. Between performances, he spent hours tucked into local clubs. It was where he made a name for himself as a performer, first working the room as an opening act at the Sherman House Hotel and then finding fame when he took up with the Tommy Dorsey Orchestra at the Palmer House.ĭuring the singer ’s heyday, he h ad the run of the streets with his Rat Pack pals and celebrities including Marilyn Monroe and Ella Fitzgerald. Sinatra claimed that he performed in Chicago more than any other city- even Vegas. Frank Sinatra may have been a blue-eyed boy from Hoboken, but he had a real thing for Chicago. ![]()
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