Tootsie in Unspooled Posted May 2 Kind of a tough choice for me. This truly is one of my favorite comedies of all time. I think the fact that a lot of its themes & plot points don't hold up as enlightened as they originally hoped to me makes it a far more interesting watch now because of it. Incidentally, I recently saw the Broadway musical adaptation of TOOTSIE and it only made me appreciate the movie more. The musical tries to simultaneously pay tribute to some of the classic scenes and characters from the film, while updating them for our modern age. A great effort is made to make the characters more likable, but it ends up undermining the characters and making them far less interesting. Michael no longer sleeps with Sandy, but she does seem to play it like they're in a romantic relationship that he ignores her in. Sandy (who is played very well by Sarah Stiles, but almost completely wasted in the role and only getting to reprise her only song twice in the show) ends up falling in love with Jeff, which seems to be a desperate move to have two characters end up together at the end of the show. The Julie character is no longer in a relationship with the Dabney Coleman character, but rather flat out rejects his advances, which yes, makes her initially stronger as a woman, but it robs her of the growth that Lange goes through in the film and because of observing Dorothy, waking up to not how bad a guy Coleman is, but to her own self worth. I think what I like about the movie is that the characters are imperfect (at best), and in the case of Michael, he's a pretty horrible guy. The triumph at the end of the film is that he's become a little bit better and is able to empathize with women a bit more, but I don't believe that he and Julie end up together. I think their walk away at the end is a portrait of two friends, and Michael has kind of cursed himself that they can never be more than that because of his lies. But that is probably all he deserves and it's happy ending enough. The musical also transplants the setting from the world of poorly written but financially stable world of television soaps to the world of Broadway musicals, which provides a lot of little in jokes geared towards the Broadway audience and almost no one else, but also makes Michael's motivations a lot more muddled. It's hard to imagine Michael, who remains a pretentiously serious actor, wanting to be part of what is perceived in the play to be a horrible Broadway musical. His big gender reveal take place on opening night rather than near the end of a successful run in the role, which means he's never able to actually achieve the kind of fame and pop culture relevance that Dorothy does in the movie because most audiences have yet to discover him. The only ones who keep telling him how brilliant he is are a small handful of actors and producers associated with the play he's in. It just doesn't work. But more than anything, I think comedy is so underrepresented on the list. There are so many great comedies that should be on the list that aren't, that I would happily replace for this, but I also am reticent to voting off one comedy with no guarantee that more would be put in its place. So I can concede to those who think that this film isn't as relevant or funny as it once was considered to be. I love this movie, but there's better comedies to have on the list. Certainly funnier ones (THE IN-LAWS deserves some love), but TOOTSIE has had a pretty lasting cultural impact, for better or worse.