16. Drew Sidora as Lucy in “Step Up”
Lucy seems sort of dumb at the beginning of Step Up; she’s pretty but has a player boyfriend who she’s impressed with because he’s older. But then it’s revealed that “she majors in dance because she can already sing” when she rocks a completely believable, fully-choreographed student party. Lucy’s cool factor skyrockets when she ends up with Mario at the end of the movie. Clearly she let him love her.
15. Joan Cusack as Cyn in “Working Girl”
At first, Cyn seemed a little like a caricature: a heavily accented girl from Staten Island with huge hair and insane make-up. But she still helped Tess in her crazy scheming to move up in the workplace, even though you can tell she was worried her best friend was going to abandon her for the big city.
14. Susan May Pratt as Mandella in “10 Things I Hate About You”
Mandella really just wanted to go to prom and got sort of tired with best friend Kat’s constant need to be different from anyone else. Though she knew that she was a weirdo for feeling like she was “involved” with William Shakespeare, she didn’t compromise her passions, and eventually got together with Michael, who liked her for who she was.
13. Lake Bell as Tipper in “What Happens in Vegas”
Bell plays a bartender with an angry side who provides much needed comic relief in this relative snoozer of a movie. It’s implied that she ends up with Ashton Kutcher’s best friend who is also weird and angry – now THAT would have been an entertaining film. Anyway, she supports Cameron Diaz’s character and, like all good sassy BF’s, encourages her to drink more.
12. Zooey Deschanel as Kit in “Failure to Launch”
The likelihood of a woman being best friends with another woman 15 years older than her is pretty slim, but Deschanel wins in this movie as a weird roommate who has an ongoing issue with birds and a definite dark side.
11. Laura San Giacomo as Kit De Luca in “Pretty Woman”
The phrase “Hooker with a heart of gold” could have been coined to describe Kit. The epitome of street smart, Kit taught “Viv” most of what she needed to know about being a prostitute. And though she was flakey, she was still supportive when Vivian didn’t take her advice and fell in love with her client, a cardinal hooker no-no.
10. Carrie Fisher as Marie in “When Harry Met Sally”
Sally must have been a little annoyed when Marie ended up happily married before her, considering she spent years listening to Marie complain about her relationship with a married man who was “never going to leave her.” But Marie really laid down the truth, even if she was neurotic. She may even deserve credit for Harry and Sally getting together with the line, “Someone is staring at you in personal growth.”
9. Sarah Parish as TJ in “The Wedding Date”
British, crass and hilarious, TJ did exactly what you’re supposed to do at a wedding, which is get inappropriately drunk and hook up with long-time also funny friend (this one’s name was Woody). TJ also didn’t tell Kat about the affair Kat’s former fiance had with her sister because like, duh, who needs to hear about that? TJ had discretion.
She also had exactly the right reaction to seeing Dermot Mulroney for the first time:
8. Mindy Kaling as Shira in “No Strings Attached”
At first glance, Shira might seem bitchy and overly self-involved, but as Emma’s best friend, she provides a reality check for Emma about how hard her life isn’t: she’s a hot doctor with a hot friend-with-benefits. This movie also features close runner-up best friend Patrice, played by Greta Gerwig, their other female doctor roommate who is a lot nicer than Shira.
7. Lizzy Caplan as Ami in “My Best Friend’s Girl”
This is a pretty terrible movie, but as she does, Lizzy Caplan saves it. Ami is a seemingly unemployed sex-positive chain-smoking loaf who turns Kate Hudson’s character Alexis into something resembling a fun person once she convinces her to stop running at dawn and actually let loose a little. Here she is pictured lending Alexis a box of sex toys.
6. Maggie Gyllenhaal as Sam in “40 Days and 40 Nights”
Sarcastic Sam is Erica’s best friend, who commiserates with her about the fact that the guy she’s seeing doesn’t want to have sex with her and supports her about getting back together with him even though he really messed up. She also asks the hard questions: “From a flower? Like, a vibrating flower?”
5. Joy Bryant as Gina in “Honey”
Jessica Alba plays the eponymous lead role in this movie, a character who is almost cloyingly nice. Her best friend Gina is far more interesting: she wears amazing clothes and calls out Honey when she starts getting all Hollywood once she becomes a choreographer. Gina also makes it known that a dude Honey thinks is helping her just wants to get in her pants. Tough love.
4. Kathryn Hahn as Michelle Rueben in “How to Lose a Guy in 10 Days”
When Michelle is first introduced, she’s a sad sack who’s been dumped by her boyfriend for coming on too strong. But by the end of the movie, Michelle gets together with the boyfriend whose pillow she squirted perfume on. “The smell is gone now, and I want it back,” he tells her, in a pretty cute scene. She also convincingly pretends to be a therapist when Kate Hudson makes Matthew McCanaughey go to couples counseling.
3. Stacey Dash as Dionne in “Clueless”
It’s a wonder that Cher and Dionne even bothered with men; they were each others soulmates. Cher might have described them as friends just because they “both know what it’s like for people to be jealous of us,” Dionne was more than that. She helped plan the perfect date with a gay man, had incredible style and got that Cher wanted to wait to have sex until she found a guy as perfect as Luke Perry.
2. Christina Applegate as Courtney in “The Sweetest Thing”
Who else would go on an insane road trip to crash a wedding of a guy her best friend had met at a club for approximately 10 minutes? And who else would prompt that best friend to keep trying for this guy even though things seem dire? Courtney knows all of Christina’s issues and, even though she has her own, ends up with a nice doctor. She also has a dirty but wicked sense of humor and lets random women feel her breast implants because they seem really real.
1. Judy Greer as the best friend in everything
Judy Greer is the queen of sassy best friend’s, most famously in 13 Going on 30 and 27 Dresses. She really nails the role in the latter film as Jane’s (played by Katherine Heigl) BFF who calls what a bitch her sister is, rocks walk-of-shame clothes after a wedding and literally slaps sense into Janes, just to name a few classic BFF moments.
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