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- 10Played the best friend: You, me and Dupree
Amanda Detmer either plays the best friends in bigger budget chick flicks, or the main love interest in direct to video chick flicks (or post-American Pie National Lampoons fare.)
She always plays the innocent type who the main character needs to change for or the unnattainably hot girl that only a nerd that doesn't have his s**t together, yet has an unbelievable amount of luck, can possibly get through to.
HERE is a great picture of her that proves that she deserves to be on this list. Thank your lucky stars that Amanda Detmer is there to make the pain of seeing a movie like the ones she's in better.
- 7Played the best friend: The Hot Chick
Anna Faris played Rob Schneider/Rachel McAdams's best friend in this movie and slowly fell in love with Rob Schneider, which means that she adheres to the rules of this list in that she 1) is the lead girl's best friend before she finds her true love and 2) decides to settle for a guy waaaaaaay below her league just because he happens to show her more attention that anyone ever has.
The fact that a girl as adorable as Anna Faris would ever "settle" for anyone is absurd, but the fact that her, as a funny and awesome chick, would ever do this for you, the common man, is an awesome concept.
And these lingering thoughts, as well as the score in whatever game's currently playing, what you need at the grocery store, or what 15 second clip is going to get you through the night, are what gets most men through romantic comedies. Having someone as hot as Anna Faris doesn't hurt either.
- 9Played the best friend: Nick and Norah's Infinite Playlist
Ari Graynor mostly plays bit parts on television, but when she's not doing that, she played the most memorable (and really only watchable) part in Nick and Norah's Infinite Playlist (that Michael Cera/Kat Dennings movie that's about two hipsters falling in love and then dealing with really douchey friends.)
She manages to not only pull-off the whole drunk-girl thing without being 100% annoying, caricature-like and SNL-fake, but manages to take a girl that is actually drunk throughout the ENTIRE movie and make her not only likable but endearing.
Also, she's blond, loses her phone in a toilet and is so drunk that she reminds you of some of the greatest nights you ever had in college every time she opens her mouth in this movie -- and the best part of her drunk girl is that she didn't even get all cry-emotional-drunk near the end, ruining the party and everyone's mood.
Ari Graynor deserves a spot on this list for being one of the many chicks who not only made a memorable appearance in a forgettable movie, but actually made it half-watchable.
- 12Played the best friend: Clueless
Brittany Murphy played one of the most hotly-turned-around and amazingly madeover women in romantic comedy history: Tai. She was a girl who had the awesome, one-of-the-guys mentality who was turned into one of the "queen bees" and then once they realized they were all being bitches, settled comfortably in the middle where she ended up being pretty much any straight dude's dream girl.
Sure, she was a little rough around the edges at first, but Tai from Clueless (that I watched in the '90s much more than any straight man with an incurable crush on Alicia Silverstone should have) is one of the greatest dream girls in the history of comedies revolving around women learning something about themselves and then making it so that the dudes that they're interested in can handle them.
- 6Played the best friend: Win a Date with Tad Hamilton, The Sister in EVERYTHING
Other than being the underdog/innocently-hot third wife on Big Love (that orgy show about Mormons,) she's managed to go from being an understandably sidelined cute chick, to being that attainable, accessibly-hot girl in romantic comedies that tends to say self-deprocating things that make you want to reassure you that yes, she's probably hotter than most chicks you've had and that yes, you'd most likely do everything that McConaughey wouldn't.
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