For this movie to work it helps to know that it was originally envisioned as a vehicle for Mickey Rooney and that Stanley Clements was an upcoming name at the time due to Going My Way. Because although it's technically an Alan Ladd film, Clements is the hero as much as anyone.
The set up is complicated - Ladd owes $20k to Bruce Cabot, which means he needs to buys a horse, which means he needs a jockey, Clements, which means Clements needs to pretend he's 17, which means he has to go to school, which means his teacher is Gail Russell who expels him on day one for being fresh, which means Ladd has to romance Russell.
This is the sort of movie that should be fun but isn't, despite the presence of William Demarest as Ladd's sidekick. Clements look like a prematurely aging old man and he got on my nerves; Ladd never gets to be a colourful Damon Runyon gangster; Gail Russell's doe eyed beauty is touching but she really falls for Ladd which makes his disdainful attitude kind of mean. It's also really nasty that Clements gets shot dead. That's full on - I found a similar problem in the other Ladd "comedy", Lucky Jordan which got very serious at the end.
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