While RomCom isn't my favorite movie genre, I've certainly watched enough of these to come up with a solid list...
*SPOILER ALERT* Some of what I love involves the endings. I've tried not to give too much away, but be warned.
1) Twelfth Night - I don't know if Shakespeare really qualifies, but this is one of my favorite movies EVER so I'm putting it on the list. Hey, two (three?) couples end up happily married!
2) Moonstruck - my family doesn't understand how I can watch a movie that stars Cher, but I think she's brilliant in this one. (She won an Oscar for the role, so I'm not alone in thinking this.) Plus, young Nicholas Cage... swoon... and the dialogue is terrific.
3) Pride and Prejudice (the Keira Knightley version) - once again, I don't know if Jane Austen really qualifies, but I adore this movie and it makes me giggle, and it ends with two - no, three - no, four couples married, at least two of them happily.
4) Four Weddings and a Funeral - I love the slightly off-beat plot. I love the lack-of-wedding ending. I love Hugh Grant and Andie MacDowell and Kristen Scott Thomas....
5) You've Got Mail - I love the gentle chemistry between Meg Ryan and Tom Hanks, and I particularly love the Golden Retriever and the houseboat owned by Tom Hanks's character.
6) Sabrina (the Audrey Hepburn version) - gorgeous, classic, and romantic.
7) Singin' in the Rain - another classic, with some great music and amazing dancing to top it off.
8) Much Ado About Nothing - I adored the team of Kenneth Branaugh and Emma Thompson while they were making movies together. Dead Again is my favorite, but it isn't a comedy, so I'm going with this one. Aside from a badly miscast Keanu Reeves, the movie just sparkles. And hey, it's by Shakespeare!
9) Stranger Than Fiction - I'm usually not a fan of Will Ferrell's star vehicles, but this one is far more than that, and manages to be funny, touching, poignant, and romantic all at once. The terrific cast of women (Emma Thompson, Maggie Gyllenhaal, and Queen Latifah) really elevates the picture.
10) Heathers - black comedy, and not entirely a romance, but I have to stick this one in. It's hysterical! Watch Shannon Doherty and Winona Ryder before they screwed up their adult lives and professional careers! Enjoy a very young Christian Slater chewing up the scenery as his character slowly goes nuts! Enjoy the not-a-typical-romance ending (I won't say more...)
And the runners-up...
My Big Fat Greek Wedding
My Best Friend's Wedding
Shakespeare in Love (again with The Bard)
The Wedding Singer
Clueless (again with the Jane Austen)