I'll Be Home For Christmas (1998)
I'm having a very hard time resolving how lazy the construction of the individual scenes of this movie was with the fact that the premise was a relatively ingenious re-imagining of The Odyssey built around an eighteen year old trying to get home for the holidays. It's worth noting I'll Be Home For Christmas did this a few years before O Brother, Where Art Thou? got a lot of attention for a similar gimmick (though - needless to say - O Brother did it much, much better). Jonathan Taylor Thomas plays Jake, the Odysseus character. Like his archetype, he's a pathological liar and conman. At the start of the movie, Jake is at college in Los Angeles, along with his girlfriend, Allie, who comes from the same town on Long Island (it's a plot point later that her family only lives a few blocks from his). If this seems absurdly unlikely, it's worth noting that you'll also have to suspend your disbelief around the film's portrayal of college, a place where nerds