Mild spoilers...
This is a good film, but it suffers from a kind of showbiz hypocrisy, and it features some flawed characterization. Judy Holliday is great as Gladys, the average girl from upstate who aspires to be somebody. And Lemmon is good (though somewhat miscast) as her friend Peter, an (aspiring?) documentary filmmaker.
The problem with this film is that though it does have a good deal of ironic awareness about it, it ultimately does not have enough. The film cleverly views and studies the ambitious Gladys through the eyes of a filmmaker, Peter (filmmaker studying an "actress" within a the context of a Hollywood satire). But though the film (through Peter) is ultimately critical of Gladys -- and Gladys comes to accept who she is for herself -- the film is never critical of Peter, perhaps because his character is never developed in a way it should be. Peter is hardly a character without flaws, but the film doesn't seem to want the audience to notice this. Perhaps the writer and filmmakers did not want the audience to think about the character of Peter too much. They just want the audience of this film to think of Peter as a surrogate director who is also "directing" Gladys (or at least trying to, and the comedy partly comes from his failure to do so). But the film would have been much more successful if it had also treated Peter -- his life, his ambitions, his obsessions, his art, etc. -- as a subject worthy of study as much as Gladys (or if not as much as Gladys, at least more than he is presented). Surely Peter's desire to be a filmmaker could and would be a subject worthy of comparison to Gladys's desire to be "somebody." And even if Peter has no serious desire or ability as a filmmaker, then his desire for Gladys (either as a sincere, genuine lover -- or as a creepy stalker) could also have been much more developed to compliment Gladys's story.
And this gets to the heart of the problem of Peter's character. Who is this guy? How and why does he come to live in the same apartment building of Gladys? By filming Gladys and turning her in to the subject of a self-indulgent "documentary," does Peter have Gladys's interest at heart any more than Peter Lawford's character (the oh-so-smooth, handsome, wealthy, advertising exec)? The film nicely sets up an interesting contrast between Gladys's two suitors: one a poor, straight-talking documentary filmmaker; the other a slick, smooth, very dubious Madison Avenue executive. But the film does not successfully convince us, the audience, that Lemmon's character is really that much better than Lawford's character. Sure, Lawford has all the trappings and moves of a creep, but in a film about one woman's weird quest to climb the ladder of New York City society and showbiz fame (as presented in this, a Hollywood film), it's very difficult to judge Lawford too much more harshly than Lemmon. Sure, Lawford plays the game better, but at least he didn't move down the hall from his object of desire like Lemmon did -- without an explanation. And he doesn't creepily keep a photo next to his bed -- like Lemmon does (though maybe this kind of attention was more acceptable in the pre-feminist 50s than it is in our stalker-obsessed times). And because of the way he overplays the character here and there, Lemmon sometimes comes off as a manipulative jerk (maybe still unknown Walter Matthau, a charming crank if there ever was one, could have played this character better?). The film doesn't shed any light on Lemmon's dubiousness here, but Lawford's dubiousness is exposed from the very first time we see his character. In this sense the film misses an opportunity because it lacks irony and suspense and does not treat its characters fairly. It is too straightforward and predictable when it could have presented Lemmon's character -- even Lawford's too -- as more complex characters than the film does in fact present them.
Also, the film judges the human desire for ambition too harshly -- especially when you think about this film as being created by Hollywood smack in the middle of Hollywood's heyday -- the 1950s. If Hollywood people (Lemmon, Holliday, Cukor, etc.) aren't ambitious, then who is? Where does Hollywood get off making a film critical of wacky ambition? (though of course Hollywood's audience is middle-America, so Hollywood does frequently have to contradict its own sense aggression here and there -- though it's rarely successful when it does). This film is best when it treats the character of Gladys with affection and bemusement -- and when Holliday shows off her wonderfully charming sense of humor. The film is weakest when Lemmon blows up at her folly in a way in which we, the audience, are supposed to accept their arguments as some kind of sitcom entertainment. But (apart from the argument on the staircase, which is well-staged and amusing) these blow-ups are neither funny nor convincing, probably because they feel like perfunctory entertainment, as though the characters were already Ricky and Lucy or the Honeymooners -- and these arguments never have any real consequences for their still platonic relationship. Furthermore, far be it from Lemmon, a documentary filmmaker who goes around filming people all over New York all day without much purpose or idea of what he is doing, to tell Judy Holliday what to do with her money and her idea to plaster her name all over New York.
Despite my criticisms, this is a charming film definitely worth seeing. Judy Holliday is a treasure in this film. However, if only more studied attention had been devoted to Lemmon's character, Peter -- and if only the film did not come down so hard on Gladys's wacky ambition (through Peter's flawed, judging eyes) -- this could have been one of the best romantic comedies ever made.
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