Some Like It Hot is similar to Toosie (1982) and Connie and Carla (2004) in that they all feature the comical and not-so-comical problems encountered when one pretends to be of the opposite sex (gender). You could delve into the fact that in each movie, the main character(s) grew to "like" their new-found feminine or male identity. In Some Like It Hot, Jack Lemmon's character actually toyed with the idea of marrying the rich millionaire played by Joe E. Brown. In the movie Tootsie, Dustin Hoffman's character kinda liked dating a man and having a non-sexual relationship with a fellow female co-worker. It gave him an inside look (an empathy) for the trials and tribulations of the world through feminine eyes. In the movie Connie and Carla, they found fame and fortune as men--something that had eluded them as female entertainers. In other words, the characters developed an appreciation, i.e., a deeper understanding of their counterpart's emotions, turmoils,etc.