I really wanted to like "On the Town" (1949), I really did. It starred Frank Sinatra, one of the musical idols my whole family looks up to, and Gene Kelly, the main lead of "Singin' in the Rain" (1952), together. It's written by the screenwriters who would later write "Singin' in the Rain" and "The Band Wagon" (1953), two of my favorite musicals of all time. It's got some catchy songs, nice costumes, exceptional dance sequences, and it had all this good stuff going for it. But the story is so painfully awkward, thin, and unintentionally semi-cruel that it utterly ruined the experience for me.
In New York City, three sailors (played by Gene Kelly, Frank Sinatra, and Jules Munshin) begin their shore leave and set out to explore the town. While on a subway, one of them (Kelly) sees an ad for an aspiring actress named Ivy Smith (Vera-Ellen) and decides that he simply must meet her. As they race around the city to find Ivy, they're assisted by two women (Betty Garrett, Ann Miller) whom the other two sailors become romantically involved with. If this plot doesn't sound good to you on paper, then guess what? The story is even worse on film. Don't get me wrong, I don't doubt that there are real-life sailors out there who'd like to meet female celebrities. All I'm saying is that it's simply impractical for a sailor to go to this much trouble for such a woman, especially if it's only for one day.
Even putting aside the implausibility, the pure coincidences, and the complete lack of realism that a plot of this sort is certain to have, I still felt it was an awkward story all the way through. The main relationship between Gene Kelly and Vera-Ellen is equivalent to long fingernails on a giant blackboard in terms of its stiffness. It doesn't help that most of the love story is focused more on when they'll see each other again as opposed to them actually sharing a connection with one another. Furthermore, what was the point to having the third sailor (Munshin) around and what contributions did he make to the plot advancement? Not only is this character completely mediocre, but his girlfriend technically contributes more to the plot than he does. What's up with that?!
Okay, I should refrain from talking about the story and instead talk about the good aspects of this film. The songs, though they mostly repeat the same rhythm over and over again, are beguiling, namely "You're Awful" sung by Frank Sinatra and "On the Town" performed by the six main leads. I particularly admire how the song "You're Awful" progresses throughout. I like how Sinatra starts out with what sounds like an insult towards his love interest and then it becomes a compliment towards her (You're awful - awful nice to be with). Given that this is a musical that obviously depends on its music more than anything else, good tunes are the least that this film can provide audiences and it does exactly that.
The dance numbers aren't bad either, namely the "A Day in New York" dance sequence between Kelly and Vera-Ellen. The way they dominate the area they have to dance in is simply fun to watch. It's not like they're just simply dancing on flat ground either, they have to dance in places where they either have to watch their step or hoist up/climb down a big stair. So that scene pays off pretty well. If "On the Town" had a narrative that was at least tolerable to sit through, maybe it would have had a better chance of working. I give this musical credit for trying to tell a story other than your simple backstage musical plot and whatnot. But based on how much of a mixed bag this film is, it's clear that stories in musicals are still, in the grand scheme of things, a work-in-progress.