In 1982 there were two classic cross-dressing comedies. The better one is Victor/Victoria, which gives the gender-bending an extra twist and explores homo/hetero confusion, not just masculine/feminine. Plus, V/V has some great musical numbers and the songs in Tootsie are embarrassingly bad. However, the rest of the film is as good as its reputation.
What’s interesting here is how filmmaker Sydney Pollack put extra effort into the script, which is credited to Larry Gelbart and Murray Schisgal, but went through the hands of many top writers of the time, including Barry Levinson and Elaine May. On set, Pollack was comfortable enough to abandon all that work for better ideas in the moment, including casting Bill Murray to mostly react to events with wry asides.
He also indulged star Dustin Hoffman whose Method process was giving him a reputation for being difficult to work with. Along with Murray, Pollack cast himself in a key role to try and throw Hoffman by blurring the line between the two characters acting and the director hitting Hoffman with stories that could come from criticisms about the actor. Hoffman ends up ludicrously defending his approach, making for some of the funniest moments of the film.
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