"Tootsie": the original Mrs. Doubtfire

In the beginning, there was Dustin Hoffman.

Actually, in the beginning, there was Tony Curtis and Jack Lemmon. But the final film of the 2009 Chicago Outdoor Film Festival was not "Some Like It Hot". Rather, the final offering of the summer was Sydney Pollack's 1982 straight-man-in-drag romp "Tootsie", which unfortunately lacks the gams of one Ms. Marilyn Monroe, but more than makes up for it with Bill Murray calling Dustin Hoffman a slut.

Whereas Robin Williams donned a dress to win back his family, and Jack and Tony did it to flee the mob, Dustin buys a new wardrobe and starts watching his calorie intake when his stubborn attitude makes it impossible for him to find acting work.

The ensuing balance of plot lines between Hoffman, his roommate Bill Murray, his quasi-girlfriend Teri Garr, his agent, director Sydney Pollack; his workplace love interest Jessica Lange, and his potential suitors Charles Durning and George Gaynes is the stuff of screenwriting manual legend. There's more story packed into the two-hour run-time than your average television show has all season. In case you were wondering, I probably hate your favorite television show as well.

Aside from the deft juggling of multiple stories, what makes "Tootsie" still relevant almost thirty years later is how it deals with the subject matter at hand. Hoffman becomes an overnight sensation because he uses his female character to talk frankly about female empowerment to a national audience. What makes it work in the context of the movie, and both relevant to when the movie was made as well as today, is that "Tootsie" acknowledges the ideas at play are not easily boiled down. Most poignantly, this is illustrated in two scenes with Hoffman and Lange. In the first, Lange confides in a Tootsie'd Hoffman that sometimes she wishes a man would approach her and be blunt about wanting to sleep with her. In the second, an undisguised Hoffman finds himself at a party with Lange, and he tries the tactic. It backfires, in the form of a glass-full of champagne getting thrown in his face.

In addition to addressing women's issues without dumbing them down or waxing poetic, "Tootsie" also admirably handles the obvious issue raised by a man in drag, namely, whether or not Hoffman is gay, or for that matter, Tootsie is a lesbian. In one of the funniest scenes of the movie, which tragically is not to be found on Youtube, Hoffman and Pollack discuss why he needs to quit the show as soon as possible because the constantly shifting gender roles are wreaking havoc on Hoffman's psyche. Despite multiple come-ons and potential love interests for Tootsie, and the extreme preparations and wardrobe considerations Hoffman must make, there are no cheap homophobic laughs in "Tootsie". Even an undodgeable kiss is dealt with only inasmuch as Hoffman didn't expect or want it - there is not even a hint of a reaction like Jim Carrey's when he figures out "Einhorn is a man" (3:00). Similar to the hysterical last beat of "Some Like It Hot", the revelation that Hoffman was in drag is met by the would-be suitors only with surprise, not with shock or disgust.

Most importantly, though, the lasting legacy of "Tootsie" throughout the years is simple: it's effing hysterical.

TOO MUCH: Early 80's synthpop soundtrack, latecomers blocking my view at the outdoor venue

COULD HAVE USED MORE: Bill Murray, Geena Davis in her underwear

FILM SNOB NOTES: Director Sydney Pollack finally relented to Hoffman's request he play the part of the agent when Hoffman threatened to quit; "Tootsie" earned Hoffman his fifth Oscar nomination for Best Actor; Bill Murray improvised every line he had in the film

IHYFM RATING: FOUR AND A HALF out of FIVE MEHS

IF YOU SAID THIS WAS YOUR FAVORITE MOVIE, I'D THINK: You either A) are a screenwriter in the sense you've bought a copy of McKee's "Story", B) have strong opinions about J Crew's fall line, or C) just have pretty good taste in movies