1. Notting Hill (1999)
Starring Julia Roberts and Hugh Grant. He's Hugh-Grantishly charming and she's ... well, she's Julia. Just a girl, standing in front of a boy, asking him to love her. The requisite "chasing the girl through crowded city streets" scene in this movie is one of the best ever.
2. Love, Actually (2003)
Hugh Grant again, this time with the glorious Emma Thompson, Colin Firth, and Alan Rickman, to name just a few of the talented actors in this movie. The scenes between Emma and Alan's characters are particularly touching. Bill Nighy is delightfully icky, but you can't help but love him. Even Kiera Knightly, who usually isn't a favorite, wins me over.
3. America's Sweethearts (2001)
John Cusack and Catherine Zeta-Jones are America's Sweethearts, once-married actors who made a string of romantic comedies together. Now they're divorced, but the studio needs them to appear together to promote their last movie. Julia Roberts and Billy Chrystal round out the cast. Hilarity ensues. What's not to love?
4. Overboard (1987)
Kurt Russell and Goldie Hawn. She's a spoiled rich socialite. He's a poor carpenter. She falls off her yacht and loses her memory. He's Kurt Russell. She struggles to find her way in a strange new world. He's Kurt Russell. The chemistry between them is unmistakable. He's Kurt Russell. Need I say more?
5. Sleepless in Seattle (1993)
A classic romance. Tom Hanks and Meg Ryan. If you haven't seen it, don't wait. It's thoroughly charming -- and I mean that in a good way :) I find myself quoting lines from this one. "It's like a little clue."
6. While You Were Sleeping (1995)
Back in the day, I didn't expect to like this movie. The premise sounded implausible, at best. But it's one of my favorites. Kinda makes you want someone to lean, if you know what I mean.
7. Return to Me (2000)
David Duchovny plays a widower still mourning the loss of his wife. Minnie Driver is a heart transplant patient who received Duchovny's late-wife's heart. Carroll O'Connell and his band of friends are scene-stealers all the way through. One of my favorites.
8. P.S. I Love You (2007)
This movie has several things to recommend it. First, Gerard Butler. Second, Jeffrey Dean Morgan. Third, Harry Connick, Jr. And Hillary Swank's pretty darned good too. Kathy Bates as Swank's mother is a great character. Does it even matter what the plot is? Barely. But the plot works and the scenery is stunning.
9. Some Like it Hot (1959)
Tony Curtis and Jack Lemmon are on the run, hiding from gangsters after witnessing a mob hit. Their only way out of town is to become members of an all-girl band. Marilyn Monroe stars as Sugar Kane Kowalczyk and Joe E Brown is hilarious as Osgood Fielding III. Wonderful.
10. Teacher's Pet (1958)
Clark Gable plays a rough-edged newspaper man. Doris Day is a journalism professor at the local college. Since Doris Day's character despises Gable's character by reputation, he naturally pretends to be someone else when he's forced to take her class. Gig Young as Dr. Hugo Pine is wonderful.
11. Truly, Madly Deeply (1990)
Juliet Stevenson and Alan Rickman in a deeply emotional movie that's also wonderfully funny. If I remember right, this was the first movie I ever saw Rickman in and I became a fan for life. Stevenson's portrayal of grief in a scene at her counselor's office is one of the most realistic I've ever seen.
12. Sliding Doors (1998)
Gwyneth Paltrow and John Hannah in a wonderful movie about chance. What if one split-second move could forever alter the future? That's what happens to Paltrow's character, and we see her life playing out in two versions, running along in parallel.
13. It Happened One Night (1934)
Clark Gable and Claudette Colbert in a wonderful romantic comedy. She's a runaway heiress. He's a reporter looking for a story. The story goes that this movie was a favorite of animator Friz Freleng, and Gable's character during the hitch-hiking scene helped inspire the creation of Bugs Bunny.