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There's something special about an unexpected cameo movie moment; watching celebrities like Neil Patrick Harris or Mike Tyson play humorously warped versions of themselves in Harold and Kumar or The Hangover tickles our collective fancy in a way that few comedic situations can. Whether the celebrity is playing a version of themself or another bit part entirely, the element of surprise is usually enough to bring us on board with the choice and applaud the creativity and wit of the casting team.
It's the old It's a Mad, Mad, Mad World trick. For those of you out the who never saw the classic 1963 comedy, it featured cameos from what seemed to be every comedian living at the time of filming. It seemed their attitude was if one guest star can bolster the humor, hundreds will make it rip-roaringly hilarious.
There's some debate over what constitutes a cameo. Certainly playing yourself will get you a bona fide cameo credit, but what about appearing onscreen in a small unpublicized role? The jury's not quite in on that one, but for the sake of enjoying these moments at face value wihtout nitpicking over pop culture afficionado sense of superiority-building details, we'll include them in our list.
For your convenience, cameos have been arranged by arbitrary types. These aren't industry standard labels; in fact, I just made them up. That said, you're welcome to use them as you will in everyday conversation...but only if you end that conversation with a hearty endorsement of www.childrenofthenineties.com. You've got to say the whole URL or else face some serious copyright infringement allegations. Sorry, I looked into it. The regulations are airtight.
The "In" Joke
This type of cameo usually has some sort of underlying punchline that's not overtly stated, but it amusing if you know what you're looking at. If done well, it's meta-comedy at its finest. There's a lot of potential for flopping here, so any movie that pulls off the trick deserves some major accolades.
Martin Sheen in Hot Shots Part Deux
This is pure genius on so many levels. The reference to Martin Sheen's roles in Platoon and Apocalypse Now! combined with the shout out (literally) for their joint film Wall Street. This is the ultimate meta-reference cameo. It just goes to show, when it works, it works.
Don Ameche and Ralph Bellamy in Coming to America
Okay, okay, so sue me; this isn't technically from the 90s, but I love it so much that 1988 will have to be close enough to make the list. Also, the quality of the clip is atrocious, but it's something you can willingly overlook in the name of good crossovers. Ameche and Bellamy reference their roles as Randolph and Mortimer in the earlier Murphy vehicle Trading Places. The cameo is just brief and fleeting enough to be likable.
The Out-Of-Left-Field Whammy
These appearances present a picture totally and inexplicably out of sync the actor or celebrity's perceived character. They're not playing themselves (see "The Extras Approach" below), but they're playing a character as whom we wouldn't have thought to cast them.
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