11. In Her Shoes
For a solid decade, it seemed like Curtis Hanson could do anything — coming off L.A. Confidential, Wonder Boys and 8 Mile. However, In Her Shoes is the versatile director’s most unlikely success, a sometimes romance that’s just as smart about relationships as it is about family. Toni Collette and Cameron Diaz are perfect as a pair of mismatched sisters with the same shoe size who share more than they think. It’s so much better than you ever expect it would be, a reminder that smart movies about adult women do exist.
12. Kissing Jessica Stein
This almost-lesbian romantic comedy is about two women who get into a relationship almost accidentally. Jessica Stein answers a personals ad, not knowing the person who placed it was female, and ends up drawn to this person, despite the fact that she’s straight. Kissing Jessica Stein is a witty exploration of the blurred lines of sexuality and an honest look at the relationships we want and the ones we need.
13. L.A. Story
L.A. Story is a weird movie miracle. Steve Martin spent eight years writing the script for this movie, working to get it exactly right, and he nails it. Martin’s comic masterpiece exists in a strange universe where you can go roller skating in art galleries and get life advice from a sentient freeway traffic sign. The movie is at once a surreal Bunuelian satire and a poignant take on our place in the universe. Sometimes the most important signs are right in front of your face — telling you to kiss the girl already.
14. Lars and the Real Girl
There’s no universe in which a movie about a guy who dates a blow-up doll should be this good, but Lars and the Real Girl is somehow close to perfect. The movie is less about Ryan Gosling’s doll than the way everyone treats her — with a strangely open-hearted acceptance. Lars and the Real Girl presents a world that we’d like to live in, a Frank Capra-esque universe that just might restore our faith both in love and in humanity.
15. The Matchmaker
The Truth About Cats and Dogs and Reality Bites are both worth your time, but as far as straightforward rom-coms go, check out this little-seen Janeane Garofalo vehicle from back in her prime. Garofalo plays a woman who goes on a fact-finding mission to Ireland and discovers the sort of quirky Irish folks you always meet in movies. However, what it lacks in originality it makes up for in genuine laughs, showing why Garofalo was the smart girl’s comedy heroine. She makes it all look effortless.