It’s a Small World.

 September 3, 1942- Sinatra sings his last show with the Tommy Dorsey Orchestra. Where?

Indianapolis, Indiana at the Circle Theater. A venue still open. It is the home of the Indianapolis Symphony Orchestra. 

How Sinatra got out of that contract is the stuff of legends, and perhaps even great gangster movies. 

Funny enough, the next great singer who was a cultural phenomenon was Elvis Presley. He too played his last concert in Indianapolis.