I have always appreciated the way that Wet Hot American Summer makes fun of not just summer camp movies, which is an easy target, but many comedy conventions that have long been overused. Especially funny is the mocking of the sports movie, where they actually discuss all the clichés, from the ragtag losers who become champions at the last moment, to the faceless evil villains. For anyone who hasn’t seen it, I won’t ruin the punchline. But the best scene n the film is where all the counselors go into town for an hour and we see them acting wacky, smoking cigarettes, then weed, then buying a huge bag of coke, getting strung out on heroin, etc., all set to happy music. I find that the musical montage is such a trite way of showing the passing of time, that I tend to reject them when they are not in comedies. So I will list the best, worst, and the most humorous mocking of said convention in a comedy.
Best: Pretty much all of Kingpin. The Farrellly brothers films apparently all clock in at 3-3 1/2 hours in rough cuts, and so the best way for them to cut them down (though they still tend to run about 25-30 minutes too long anyway) is by cutting the gags down to the punchlines and showing them in a musical montage. The only one of their films I really enjoy is Kingpin, since the humor is consistent, and the pacing problems that they have in their other films is smoothed over by the constant silliness. The final bowling sequence set to ELO’s Showdown is pretty much the apex of their skill (of course helped immensely by Murray’s combover).
Worst: Pretty much all of Look Who’s Talking Too. This entire 81 minute movie is padded with musical montages, I counted 8, simply to cash in on the success of the first film. There aren’t really any jokes in these scenes, they just show the characters doing things, like walking in the park or buying groceries. But apparently Amy Heckerling thought if she covered the scenes in popular 50′s music, no one would notice.
Parody: Wet Hot American Summer, or perhaps the romance sequence in The Naked Gun, where we see them coming out of Platoon laughing hysterically.