One way to tell if some of the films on the AFI list hold up is if Connor enjoys them. A film that translates well across generations surely must be a worthy film. Given that, 1982’s  Tootsie definitely belongs on the AFI list.

Tootsie is a funny film that doesn’t rely on the silliness of Dustin Hoffman in drag to get laughs but rather provides its laughs through the brilliant writing of Larry Gelbart and others. Sure, Hoffman is not exactly an attractive woman, and there are a few moments of physical humor thrown in because it’s always funny when a man tries to walk in heels, but the dialogue makes this film so amazing. Here’s an example of my favorite rant by out-of-work actor Michael Dorsey:

Michael Dorsey: Are you saying that nobody in New York will work with me?
George Fields: No, no, that’s too limited… nobody in Hollywood wants to work with you either. I can’t even set you up for a commercial. You played a *tomato* for 30 seconds – they went a half a day over schedule because you wouldn’t sit down.
Michael Dorsey: Of course. It was illogical.
George Fields: YOU WERE A TOMATO. A tomato doesn’t have logic. A tomato can’t move.
Michael Dorsey: That’s what I said. So if he can’t move, how’s he gonna sit down, George? I was a stand-up tomato: a juicy, sexy, beefsteak tomato. Nobody does vegetables like me. I did an evening of vegetables off-Broadway. I did the best tomato, the best cucumber… I did an endive salad that knocked the critics on their ass.

A juicy, sexy beefsteak tomato! And some of the best lines are left to Michael’s playwright roommate Jeff, played deadpan by Bill Murray. Teri Garr is classic, and Charles Durning is great as Jessica Lange’s smitten dad. And Dabney Coleman is perfect as the chauvinistic soap director. Jessica Lange was just ok, but somehow she managed to get an Academy Award for best supporting actress. You gotta feel for Dustin Hoffman being nominated against Ben Kingsley for Gandhi — he never had a chance. Gandhi also rightfully beat Tootsie for best picture.

I can’t provide praise for Tootsie though without saying something about director Sydney Pollack, who not only directed the film but acted in it as well, stealing some scenes as agent George Fields. Pollack was a great director who along with Tootsie is well known for directing Absence of Malice, Out of Africa, The Way We Were, The Firm and many more. Pollack liked to act as well and over his career he had some memorable roles, none better than George Fields. He made some cameos in Entourage, The Sopranos, Michael Clayton, Husbands and Wives, and many more. The guy was a Renaissance man and we lost him too young.

Next Up: Unforgiven