1) The meet cute. This is a term used by film studies people to describe the situation, always humorous and unintended on the part of the characters, when the two people meet. In Serendipity, it's selecting the same pair of gloves at the same time and having to fight over it.
2) The love-hate dynamic. The said couple is intensely attracted to each other, but at first is reluctant to admit it so they are often dismissive of each other. It makes for great comedy as they try and battle the sexual tension.
3) The best friend. Usually a fat broad or a lonely gay guy, the best friend is dependable but never outshines the lead. The best friend in modern romcoms is almost exclusively played by Judy Greer. (No kidding, she is in almost all the romcoms! As Timothy Spall is to ugly roles, Judy Greer is to the best friend role).
4) The break up. After dating and really enjoying each other for a while, a very obvious misunderstanding causes the couple to break up. The girl sits on the couch, wearing frumpy clothes, and watches TV while eating out of an ice cream carton (see: Bridget Jones). The guy pours himself into his work and hangs out with his friends playing sports but missing his girl.
5) The get back together. Against their every wish, the couple is thrust back together in a humorous situation (a la the balloon ride scene in The Ugly Truth) and then reconcile and fall in love all over again.
The appeal of romcoms lies in this predictability. You go to the theatre expecting the outcome, and therefore can sit back and enjoy it without being preoccupied.
Without further delay, the best romcoms:
10) Shakespeare in Love - 1998. A story about Shakespeare falling in love that is built around the plot line of Romeo and Juliet and Twelfth Night, this movie is one of two romcoms to win a Best Picture Oscar. To say that it's excellent is a disservice to this movie. Gwyneth Paltrow stars as the love interest of Shakespeare, played by the long-necked Joseph Fiennes. Judi Dench's less than 15 minutes on screen as Elizabeth I is so captivating, that she won an Oscar. I adore this film.
9) Something's Gotta Give - 2003. I'm not too much of a fan of Diane Keaton and her bizarre turtle-neck sweater fetish, but this is a great movie. Jack Nicholson is dating her daughter, but as the two spend more and more time together, they fall in love. Along the way, Diane goes out with a handsome young doctor, played by a surprisingly not-wooden Keanu Reeves, which foils the relationship of the crusty Jack Nicholson and Amanda Peet. The heart attack scene is so funny. I love the ending in Paris, where they finally confess their love for each other. It's Complicated has nothing on this movie.
8) The Very Thought of You - 1998. Joseph Fiennes reappears on our list in this underground British romcom. A really pretty girl abandons her problematic life in America and buys a $99 ticket to London on a whim to start over. Three men, all very good friends, fall in love with her but as they tell each other their stories, they don't realize it's the same woman. Joe ends up with her in the end. Great humor, and a very magical story, and marvelous acting make this clever movie a departure from the norm.
7) Bridget Jones's Diary - 2001. Renee Zellwegger gained a lot of weight for her role as the large ditz with an out-of-her-hands life. Based liberally on Pride & Prejudice, the plot is the same as its source material. Hilarious jokes and frank British sexual humor spruce it up, along with the normally dull Colin Firth parodying himself as Mr. Darcy. A classic of the modern genre. 
6) 13 Going on 30 - 2004. Jennifer Garner plays a girl who desperately wanted to be popular in high school. She gets sent forward in time to find that she's a successful business woman and popular. But when she reconnects with her best friend from school, and falls for him, she realizes that being popular made her a mean person and gives it all up to go back. The 80s flashbacks to high school are excellent, with a Madonna soundtrack and funny pop culture references. The scenes of Jennifer Garner getting used to being 30 are hilarious.
5) The Awful Truth - 1937. Cary Grant and Irene Dunne star as a couple who are married but are getting a divorce. They spend a humorous evening together going to a party, then travelling to her uncle's house confronting the issues in their relationship. In the end, they wind up falling back in love. Two memorable scenes include the singing scene at the party, and the car falling down a slope near the end. Though old, this is a classic of the genre and is humorous and safe for the whole family.
4) Bringing Up Baby - 1938. Another oldie but goodie. A tiger, a stiff by-the-book guy, and a vivacious girl collide in a rollicking, humorous adventure. The film is heavy on slapstick with the tiger, but it's a true classic. Katherine Hepburn is impeccable as usual, in a comedic departure from her usual dramas. Cary Grant stars as the straight laced man who falls in love with her.
3) The Wedding Singer - 1998. Adam Sandler plays a loser who teaches music, who falls in love with Drew Barrymore, a nice girl who's dating the wrong guy. Set in the 1980s, the film is rife with hilarious references to the pop culture of the decade. The soundtrack, featuring Madonna among others, is one of the best compilations ever. It is a virtual greatest hits of the decade. The supporting cast is spot on, and the humorous but touching ending on the plane is silly but fun. This movie is really just a good time as any!
2) Catch and Release - 2006. I was hesitant to include this on the list at first, because it's more of a drama. The radiant and under appreciated Jennifer Garner plays a girl whose fiance dies on their wedding day. She falls in love with his best friend, the ne'er-do-well photographer Fritz (who is currently starring as the cop in "The Crazies"), while overcoming her grief and the revelation that she didn't know her fiance as well as she thought. The filming is beautiful, and the movie is actually a step above its own genre. The humor of the movie is largely provided by Juliette Lewis, playing a hippy, and Kevin Smith, who plays Fritz' fat but funny roommate. A touching ending pulls on the heart strings. This is a marvelous gem of a movie.
1) Never Been Kissed - 1999. Drew Barrymore plays a reporter for the Chicago Sun Times who goes undercover as a high school student. She's was a loser then, and starts off as a loser now. But then she falls for her irresistible English teacher, played by Michael Vartan. She masquerades as a popular girl but then everything blows up in her face as he discovers her deception. The ending is amazing, and makes this movie earn the number one spot. Drew is funny as usual, and really carries the movie. Alias fans will appreciate Mike's turn as the teacher. Oh, and Madonna's Like a Prayer is in this movie too.
Worst romcom: Maid of Honor
Honorable mention best romcoms: The Wedding Planner and The Proposal
To the cashier at the Borders on the corner of Halsted & North in Chicago, I've seen The Holiday, it wasn't as good as you said.
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This is a great post! Very detailed- I liked the run down of the romantic comedy conventions in the intro. You include a good variety of movies- I like that you have movies from the '30's along with stuff that's just a few years old. There's something about top ten lists that are always fun. By the way, I counted three Madonna mentions- Caresse, I was mentioned!
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