When it comes to the quality of rewatchability, comedy is probably the genre that is most problematic. Since comedy is so highly dependent on a quality of surprise, it tends to suffer from familiarity in a way that even horror does not. This aspect that is peculiar to comedy in a way that does not apply to other genres doubtlessly accounts for the tendency for comedy movies we loved when we were kids may not be quite as beloved when we reach middle age.
One of the hallmarks of a great comedy is therefore its ability to be enjoyed on multiple viewings. Rewatchability is a funny thing, however. Some comedy films stand up to repeated viewings not so much because the jokes can withstand the absence of surprise so much as the opposite. We know what's coming and there is a certain sense of joyous expectation. I suspect this is the explanation for why "A Christmas Story" continues to be successful for WTBS on its annual 24 hour marathon. Flick's tongue not coming loose from that flagpole has long since failed to surprise, but it is still possible to laugh. The anticipation of Darren McGavin's intensely idiosyncratic rendering of the line "Dagnabbit….blowout" makes it nearly as funny as that first time when it came as a complete surprise.
Rewatchability of a comedy can also be attributed to nostalgia. While some comedy movies are constructed from a style of humor that we outgrow, others contain an element that makes the funny scenes produce a warm fuzzy feeling of comfort more than laughter. "Abbott and Costello Meet Frankenstein" is nowhere near as funny as it was when I was a kid, but it remains eminently rewatchable to me because it brings on a sense of nostalgia from those days of staying up late on Saturday night when it would air on "Popcorn Theater" on one of my local stations.
Then there is the comedy that can be enjoyed even more on subsequent viewings because it contains a level of humor that went over your head the first couple of times you saw it. "Dr. Strangelove" is an example of that rarest of all cinematic commodities: the comedy that gets funnier the second and third time you watch it. Some comedies are funnier as adults because you get the double entendres and other adult humor that you missed when you saw it first as a kid. "Dr. Strangelove" does contain comedic bits that require a bit more maturity and seasoning, but it also remains highly rewatchable because you may be more politically educated the second time around or even because you have become more aware of filmmaking techniques that lead you to appreciate it on a repeated viewing.
One of the most rewatchable comedy films of the 21st century is the quirky little below-the-radar offering titled "The Sasquatch Gang." My kids and I have watched this movie together about four or five times and it never fails to make us laugh. Part of the rewatchable of "The Sasquatch Gang" is the ability to discover subtle little bits of humor that are easy to overlook as a result of its low-key approach to developing comedy out of character rather than merely connecting a series of jokes. Part of the rewatchability is due to that very aspect itself. These characters feel like real people rather than manufactured joke machines. "The Sasquatch Gang" is an example of the comedy that is rewatchable because it feels like a reunion with old friends.
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