Tootsie

In the film Tootsie, Dustin Hoffman plays a struggling actor named Michael Dorsey. Because Dorsey struggles to receive any work due to his poor reputation for being difficult to work with in the industry, he gets the inspiration to dress as a woman named Dorothy, so no one can recognize him, and audition for a role as a woman in a soap opera series. He gets the part because he plays a strong, assertive older woman, which his female friend was struggling to channel due to her softer demeanor when auditioning for the same role.

After receiving the part, Dorothy becomes a feminist icon both amongst her colleagues and across America with her improvisations on set and resilience to refuse any disrespect from the male characters with which she works. Dorothy particularly connects with her co-worker, Julie, whom Dorsey finds attractive.

For the following video, click on the top right-hand corner Playlist button and click on #6.

Relative to other crossdressing films at the time, such as Mrs. Doubtfire, Tootsie was perceived as more progressive at the time it was released. Dorsey actually comes to love and cherish his more feminine side through Dorothy, as shown by his fixation on enhancing her image via makeup, jewelry, and wardrobe. He takes his role as Dorothy very seriously and viewers can see his gradual infatuation with her by the way he invests so much time in her appearance, however, this is juxtaposed by Bill Murray’s character, Dorsey’s friend, who expresses his concern for this obsession taking over his masculine identity. The audience is seemingly supposed to side with Murray and laugh over the absurdity of Dorsey’s enjoyment in this role.

However, regardless of however genuine Dorsey’s connection to his more femininity is, it is undermined by his ulterior motives to pursue his co-worker Julie in a heterosexual romantic way, which emphasizes the compulsory heterosexuality conveyed in these films.

Additionally, as alluded to in my theory section, the audience is “allowed” to enjoy Dorsey’s fixation with Dorothy because it was a temporary transgression. The audience can take comfort in the fact that even though Dorsey becomes Dorothy, he is still a straight man behind the wig, makeup, and dress. It is harmless because at the end of the film, Dorothy reveals herself as Michael Dorsey and there is a sense of “normalcy” which is resumed. Dorsey is allowed to pursue Julie as a straight male.

It also worth noting that in a lot of these cisgender male characters crossdressing as women cases, these women are viewed as traditionally less attractive than their cisgender female counterparts, which is supposed to further empathize the notion of how “unnatural” and “abnormal” a male-to-female transition is. In some cases, such as Mrs. Doubtfire, they use fat-suits to further distinguish the natural beauty of cisgender characters to the forced beauty of their cross-dressing characters. This is because the more realistic and passable the drag is, the more credence is given to the character and the more it pushes heteronormative boundaries, which is controversial within Hollywood, especially in the 80s.