It seems to be a trend that Sinatra needs an aggressive, opinionated, cute (but not drop dead gorgeous) girl to pair up with. This actually makes him more endearing and seemingly in reach for the girls in the audience pining after Frank. In Anchors Aweigh, It Happened In Brooklyn, and On the Town, Sinatra ends up with a blonde, boisterous, Brooklyn girl. This phenomenon is especially obvious in On the Town, when the female cabbie pulls over and nearly jumps Sinatra--something in which he seems disinterested. Thinking over it, while Sinatra eventually reciprocates the love or attraction, he at firsts seems either oblivious to the glaring signals or feels like he has better things to do with his time. Just when the audience could believe that Sinatra either failed to hit puberty and like girls or that he may be more interested in the Gene Kellys than the Katherine Graysons, Sinatra kisses the girl and shows some passion!
On the Town has all the workings of a cheesy yet cute musical. Start off with three attractive (or at least attractive enough) sailors on leave and add in three women to pair them off. There are several hard to get sequences, but there is no doubt in the audience's mind that the blunt taxi driver would win over Sinatra and Gene Kelly would get a date with Ivy Smith. Ozzie (Jules Munshin), the third and most comedic sailor of the trio, was paired with the over-the-top, boy-crazy and nerdy Claire (Anne Miller). The women characters were all perfectly crafted to complement the models of masculinity which Sinatra, Kelly, and Munshin portrayed.
When first getting off the boat, the boys all sing together and sight-see together. Not until they take a rest and start talking do the differences in personality and interests become apparent. Kelly proclaimed himself the female-expert, seemingly invincible and unstoppable when pursuing a woman. As typical for his characters, Kelly seemed to puff up his own reputation and it only faltered when he realized that it wouldn't get the girl. Kelly was the strong, wolf-like character, chasing his woman who was perched on a pedestal around town. If the girl were easy to get, Kelly wouldn't want her (most likely). Sinatra's preoccupation with sightseeing even when having the option of spending time alone with a more than willing female in her apartment made him seem oblivious to the allure of females. He kept being obstinate and even ticked off by the cabbie attempting to seduce him (as if he had a better usage of his time). Finally his will was broken and he also gave into temptation (which I didn't know he harbored until then)when he started passionately kissing the cabbie in the apartment. Sinatra seemed to have come of age in the middle of the film and his song on the top of the Empire State Building exemplified that, while Sinatra was endearing, his characters tended to lack the smooth technique of Kelly. Lastly, Jules seemed to fit into the comedic role in the film. He wanted a girl and Ann lusted after the male gender, so they inevitably fell together and began their romance with no delay. Jules's quirky personality needed some female who shared that slight odd-ness with him. Out of all of the men, and even though he was the first one to have something physical happen with a girl on the trip, he seemed to be the least attractive and his role was purely to provide laughs, not to induce the swooning.
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