#11. On the Town – 1949
(#19 on the AFI list)
On the Town… also known as the movie where a 34-year-old Frank Sinatra pretends he has never been to New York.
The directorial debut of Gene Kelly and Stanley Donen, this film is an adaptation of the stage musical of the same name. Kelly, Sinatra and Jules Munshin play three sailors on a day of shore leave in the Big Apple, and Betty Garrett, Ann Miller and Vera-Ellen play their love interests.