In response to a reader question, here's a starting point list of romantic comedy films. I'm mostly going by memory and what's in my collection. This list is likely to grow or change because I imagine titles will be popping into my head for days. (And, it's already happening)
Classic films (films that came out before I was born)
The Philadelphia Story (love, love, love -- fabulous dialogue)
Bringing Up Baby
The Awful Truth
It Happened One Night
My Favorite Wife (there's a later version called Move Over Darling, with Doris Day and James Garner, but I like the B&W Irene Dunne/Cary Grant version better)
The Shop Around the Corner (far superior to the remake, You've Got Mail)
Charade
Historical (set in a time period different from when they were made -- costume romantic comedies)
Pride and Prejudice -- the miniseries with Colin Firth (I wasn't crazy about the film version with Keira Knightley)
Sense and Sensibility (the Emma Thompson version)
Emma (just about any version -- I think I've liked all the recent ones. There was an A&E version with a young Kate Beckinsale, then there was the Gwyneth Paltrow big-screen version and then a more recent PBS miniseries)
A Room with a View
Miss Pettigrew Lives for a Day
Much Ado About Nothing (the Emma Thompson/Kenneth Branagh version)
Down With Love (a spoof of the early 60s Doris Day films)
Shakespeare in Love
I Capture the Castle
Cold Comfort Farm
(the bottom three might not technically be romances as two of them don't have the happy romantic ending and one hardly deals with the romantic relationship, but they still scratch the romantic comedy itch for me)
Contemporary (meaning I saw them first-run or could have seen them first-run)
Not all of these are brilliant movies. I may have some issues with some of them, but for the most part, I don't think any of them are truly bad movies that I would consider "cynical."
Bridget Jones's Diary (but not the sequel)
While You Were Sleeping
When Harry Met Sally …
Love Actually
The Holiday
Letters to Juliet (I've only watched it once and liked it then, but I haven't had a chance to revisit and be more analytical about it)
You've Got Mail (but not as good as the original)
The Very Thought of You (had a different title for British release -- kind of obscure, but very interesting because it plays a lot with perception and viewpoint)
I'm With Lucy (another obscure one, but interesting because of the story structure because it's non-linear -- the heroine is getting ready for her wedding and telling the story of how she met her husband, and then the stories of several men she dated in the past year are woven together, but we don't know which one she's marrying)
Clueless
Four Weddings and a Funeral (except for the ending)
Mrs. Winterbourne
Notting Hill (except for the ending)
Office Space
The Fabulous Baker Boys
Working Girl
Hope Floats
Sleepless in Seattle (though I really don't think of this one as that romantic, since they don't even meet until the end)
Romancing the Stone
Paranormal/Fantasy
Tangled (yes, the cartoon, the one Disney fairy tale movie that is structurally a romantic comedy)
Kate and Leopold (trivia note: this screenwriter wrote the Enchanted, Inc. screenplay that didn't get produced. I'd love to see what he did with it to see if I like it or to see why Universal didn't like it)
Just Like Heaven
Sliding Doors (I'm not sure how comedic this one really is, but it works when I'm moody and need to both laugh and cry)
The Princess Bride (not really focused on the romance, but still, it has to be on all lists of movies to watch)
Enchanted (duh, can't believe I forgot this one)
The Bad Ones
To be honest, I've enjoyed some of these, but mostly, they irk me and I wish they could have been done better
Leap Year (just a few tweaks to the script and it could have been decent)
Raising Helen
Something Borrowed
28 Dresses
Knocked Up (I know this was very successful, but I hated it, mostly because I loathe that overgrown frat boy man child thing)
Must Love Dogs (I read the book, but somehow the movie was bland)
The Wedding Date (an abomination -- they completely missed the point of the book it was based on)
New in Town -- I couldn't get past the first 20 minutes on HBO, so it has to go on a "bad" list
Because I Said So -- I think I have a rant written somewhere about this one. The problem isn't so much the cynicism behind it as it is the fact that it doesn't seem to realize it's about pathological behavior. It had potential, though
Addicted to Love -- something Meg Ryan would probably want off her resume. She tried to act edgy. It didn't work.
French Kiss -- I saw this on a date and still barely remember it
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