1. The Rules Of Attraction (2002)
After he co-wrote Pulp Fiction and before he went to jail for vehicular manslaughter/DUI, Roger Avary directed a somewhat underrated and thoroughly entertaining Bret Easton Ellis novel adaptation starring Dawson’s Creek‘s James Van Der Beek. It’s a very stylish and good movie. Bonus points for the inclusion of Donovan’s “Colours” on the soundtrack.
2. Superstar (1999)
This comedy, starring Molly Shannon alongside Will Ferrell, got pretty mediocre reviews when it came out, but I think it’s funny and charming. Shannon plays her Saturday Night Live character Mary Katherine Gallagher, a nervous Catholic schoolgirl who has a habit of putting her hands in her armpits and then sniffing them (lol).
3. Sleeping Beauty (2011)
This movie is beautiful, weird, and sexy. Sign me up! The very fetching Emily Browning plays a young university student who starts doing erotic work. This kind of erotic work involves sleeping in the bed with, but not having sex with, paying customers. Pretty pervy, so if you’re easily offended/creeped out, not for you. However, if you like a morally ambiguous, sexually tense art film, then you might love it.
4. A Woman Is A Woman (1961)
This is a good place to start if you’re new to Jean-Luc Godard movies. It stars the lovely Anna Karina, Godard’s real-life wife at the time, as a striptease artist with a baby dilemma. She wants a child, her boyfriend doesn’t, but his friend does. What to do? The use of color is striking, and it’s a fun, playful tribute to (and deconstruction of) American musical comedies.
5. Holy Motors (2012)
This critically acclaimed French film by Leos Carax is one of my all-time favorites. It is a unique cinematic experience: a day in the life of a man who waves goodbye to his family, gets into a limo, and is handed a mysterious folder of assignments — each assignment requiring him to change his entire appearance, so that each time he steps out of the limo, he’s a completely different person, one time a poor old beggar woman, the next a cold-blooded assassin. This results in a series of unique vignettes, each as captivating and surprising as the next, making this a ride rather than a conventional narrative. Surrender to it and you might be excited by the unpredictability, the imagination and brio of the director, and the thrilling performance of its star, Denis Lavant.
6. Fallen Angels (1996)
Fallen Angels is the first Wong Kar-Wai movie I ever saw, and it can be a gateway drug to his many other good films, including my personal favorites, 2046, Chungking Express, and Happy Together. He’s a great director, he creates amazing moods with his beautiful, idiosyncratic cinematography and use of music, and he commonly sets his movies in 60s Hong Kong, complete with gorgeous costumes and sets. A romantic, beautiful filmmaker.
7. Metropolitan (1990)
Whit Stillman’s first film, about upper-class young people at debutante balls during winter break, is charming and fun. Stillman is known for his dialogue — the characters in this movie talk in an exaggerated, gently satirical version of young educated New Yorker. There’s also romance in it and lots of music (another Stillman trademark). I highly recommend all of his movies.
8. Clueless
Alicia Silverstone in a wink-wink comedy about a hilariously oblivious valley girl. The characters and script for this are even more fun than I remembered. Includes Paul Rudd in an Amnesty International t-shirt drinking OJ out of the carton while Radiohead’s “Fake Plastic Trees” plays in the background.
9. Y Tu Mamá También (2001)
If you haven’t already seen this beautiful movie directed by Alfonso Cuarón (Children of Men, A Little Princess, that one Harry Potter movie that was better than the others) and starring Gabriel Garcia Bernal, I highly recommend it. Features a good story — about a road trip shared by two teen boys and an older woman — beautiful cinematography, and some pretty hot sex scenes.
10. Manhattan (1979)
This film, one of Woody Allen’s all-time greats, is a gorgeously shot paean to his hometown as well as a compelling love triangle involving an older man, a young girl, and his best friend’s mistress (the wonderful Diane Keaton). This one gives you laughs and beauty and some things to think on. 
