As a rule, comedies about crossdressing don't work, perhaps because the premise lends itself to a limited set of gags that generally aren't that funny. Tootsie, while far from the second funniest movie of all time as the American Film Institute's 100 Laughs list suggests, works because it neatly avoids all the cliches and keeps its unswerving focus on the hearts of its characters. The film's humor, then, comes naturally from the situations that result, not from the mechanical churning of the formula wheel. Of course, great performances help. Dustin Hoffman makes a startingly convincing woman, and around his are other wonderful performances by Sydney Pollack, Bill Murray, Charles Durning, and Jessica Lange, who won an Academy Award for her performance. Pollack, who also directed, shares the funniest scenes with Hoffman, as the two characters quibble about how crazy and absurd Hoffman's charade is.

Back when the web was an unknown and the Internet was still the province of businesses and universities, I went through a (brief) stage where I spent time on IRC, a distributed chat room server. I had heard, through friends, about how differently one was treated if one had a feminine sounding nickname, and so, as an experiment, logged in under the name "Valerie." The difference was immediately apparent, and it only took a few minutes before I logged out, feeling sickened -- sickened not from any particular behavior I observed but from the realization of how much a false representation of gender messes with people's heads. Gender defines so much of who and what we are, to ourselves and in the minds of others, and hormones and pheromones do more than we often realize to direct behavior. To pose as a member of the opposite sex and form friendships and trust in that guise crosses a pretty serious line. Crossdressing comedies that don't get this therefore wind up feeling trite and artificial.

Tootsie gets it, and although one could argue that the mess created by the end is more than the ending could realistically fix, the film's understanding of the gravity of its subject is sufficient for it to feel genuine.