"An unemployed actor with a reputation for being difficult disguises himself as a woman to get a role in a soap opera." IMDb
In the vast list of movies about cross-dressing, Tootsie is one of my favorites. Definitely top two...right there next to Mrs. Doubtfire...at any rate, it's way better than all the Big Momma's House movies. To Wong Foo...there's I think I've named them all now... Okay, I guess Some Like it Hot has cross dressing in it too...and Victor Victoria, but that's different...I'm getting off track.
Dammit, Sorority Boys...
Anyway, Tootsie is about a man named Michael Dorsey(Dustin Hoffman) who, while actually being a very talented actor, is also a huge pain in the ass and very difficult to work with. He had pretty much pissed off every director in town. Blacklisted I believe is the term. Even his own agent tells him that no one is willing to work with him. So, he pretty much says, "oh yeah!?" and, with no set up or warning, the immediate next shot is of Dustin Hoffman walking down a crowded street dressed as a woman. But I suppose I'm getting ahead of myself. There's a couple things I gotta fill you in about first...
So, Michael has a roommate (Bill Murray!) who is a playwright and he's got this great play that he's writing in which Michael would play the lead. But, they can't get anyone to produce it cause again, Michael is a pain in the ass. Also, there's Sandy, (Teri Garr) who Michael is running lines with for a part in a soap opera she is auditioning for...and now you're up to speed.
Now Michael, for lack of any better ideas to raise money for Bill Murray's play, puts on a dress and makeup, calls himself Dorothy Michaels, and auditions for the soap himself. Since he's a great actor, he totally pulls it off! From there, he keeps getting hit on by other male actors, he gets set up on dates with older men, he falls for his costar who is a women (Jessica Lange), but clearly she doesn't know he's a dude...it's hilarious.
I don't hand out the 4 star rating very often, but this one is a classic. It's well cast, well acted, well paced, it's silly yet realistic...Seriously I just think this movie is great, though I doubt many people my age would agree with me. This is one of those that I honesty think could be remade, and I think Robert Downey Jr should do it. I'm just throwin' it out there. It could work!
Shit, White Chicks....but fuck that, that movie sucks...like...hard. Anyway, go check out Tootsie!
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