When Michael Dorsey, a pretentious and elitist actor, finds it difficult to get work on the New York theater scene he takes the steps any logical privileged man would; dressing as a woman to try and get a job. In Tootsie, adapted from the classic 1982 movie, this is exactly what happens. And while it's good musical comedy, you can't help but feel how dated the storyline actually is.
While Tootsie is fun to watch, with some stellar comedic performances from Sarah Stiles as Michael's friend Sandy, the neurotic struggling actress who knocks it out of the park with the song "I Know What's Gonna Happen," and Andy Groteleuschen as Michael's roommate Jeff, who gets the first hand look at the lengths to which Michael attempts to get a job, before getting to gleefully sing about how badly he f***ed it up. And while the songs are fun, if not hugely memorable, and the physical comedy is a standout aspect of the show, the one thing that does not hold up is the plot.
Santino Fontana plays Michael, who later becomes Dorothy. As Michael, Fontana plays a rude and arrogant actor, so arrogant in fact that not even his agent really wants to work with him. But as Dorothy, Fontana plays a woman who makes her voice heard and changes a musical for the better, while accidentally attracting the attention of two men and falling in love with his costar Julie (Lili Cooper). And remember, none of these people know the trick that Michael has played to get a job.
Yet, Tootsie assumes that Michael's life will be easier now that he's a woman despite the fact that he's still the same whiny person he was before. When everything falls apart for him, he's apologetic. But when the gender roles are messed up to the point where Michael is excused for what he has done. However, all the audience got to see was his life get easier once he put on a dress.