This is in my opinion. I know it's different from a lot of other people's. I haven't seen all rom-coms, and I'm someone who's impressed easily (most of the time.)
1. (500) Days of Summer. "An offbeat romantic comedy about a woman who doesn't believe true love exists, and the young man who falls for her." (IMDB.com)
(500) Days of Summer is the number 1 rom-com of the '00s for a reason. It's hard to pull off a movie like this (romantic, unpredictable, unique, comedy, drama.) The movie follows Tom Hanson, a young greeting-card-writer-who-wants-to-be-an-architect living in LA. One day, a girl, Summer Finn, is hired to be Tom's bosses' assistant. He shortly thereafter falls in love with her. The movie is basically about Tom looking back on the days they spent together before she "dumped" him (this is revealed at the start of the movie.) A well put-together indie film 100% worth checking out.
2. Eternal Sunshine of the Spotless Mind (IF you'd consider it a "rom-com.")
"A couple undergo a procedure to erase each other from their memories when their relationship turns sour, but it is only through the process of loss that they discover what they had to begin with." (IMDB.com)
I only put this second because I'm not so much of a drama fan. Though, Kate Winslet is a top 5 favorite actress and Jim Carrey is a top 20 favorite actor. Both give great performances. I have only seen this once, and that was at the beginning of my movie-buff-obsession thing I've got going, so I wasn' t paying upmost attention. Luckily I'm seeing in my film class again. I do recommend seeing it though. Great movie.
3. Bridget Jones's Diary. "A British woman is determined to improve herself while she looks for love in a year in which she keeps a personal diary." (IMDB.com)
I looove this movie. It's very good. It's a well put together rom-com about Bridget Jones (Renee Zellweger) and the 2 men who like her. I put this as #3 because it's a very funny movie (and, from what I've heard, most people expect more romance than comedy in rom-coms) while keeping good pacing and surprise. The movie ranges from predictable to unpredictable and has a nice cast. The leads are perfect. I recommend you check this out too if you haven't seen it (though I'm probably gonna end up saying "I recommend you see this" at the end of every paragraph I write on a movie.)
4. Love Actually. "Follows the lives of eight very different couples in dealing with their love lives in various loosely and interrelated tales all set during a frantic month before Christmas in London, England." (IMDB.com)
Lol I'm actually happy that it at least got a 7.8 on IMDB.
Anyway, this is #4 because it's a good original story. I don't know if it is the ACTUAL first of its kind (more than 3 love stories intertwined) but it's the first I've seen of its kind. It's more drama than comedy from what I've seen, but the cast is all-star! Great cast! Great soundtrack as well nonetheless. Some people find it hard to keep up with as many stories as there are, which is a poor excuse for rating it bad. I don't see why people find it difficult to keep up with this movie. Anyway, the movie has some nice dialogue. I love how diverse the stories are, too. They're not just a bunch of stories thrown together like in the 2010 movie Valentine's Day, they seem to be structured well. Different age groups as well. Ranges from kids to older adults. Check the movie out, it's fun.
5. The Holiday. "Two women troubled with guy-problems swap homes in each other's countries, where they each meet a local guy and fall in love." (IMDB.com)
I'm prepared for a shitload of disagreement on this lol. Most people will recognize the director, Nany Meyers, from her movie The Parent Trap (1998.) She's a very good screenplay writer and her direction is good too. Something interesting about the movie is that Dustin Hoffman's part wasn't intended. He was driving by, saw the cameras, knew Nany Meyers and got that short little part at the Blockbusters. But apart from that, the cast is the first positive thing about this movie. Cameron Diaz, Jude Law, Kate Winslet (GREAT to see her in a rom-com), Jack Black, Rufus Sewell, and the legendary (IMO) Eli Wallach! Such a great cast. Cameron and Jude had great chemistry and so did Kate and Jack. The sountrack and score are worth praise as well. The score fit perfectly, though that's no surprise judging on how good of a composer Hans is. One of the only things I didn't like about this movie is how long it is. I do understand why it's long, though. 2 love stories is hard to control under 2 hours. Maybe cutting a few scenes short here and there would make this movie better. But other than that, the movie is fun to watch and, AGAIN, I recommend it completely. It is my 2nd favorite rom-com and I can't count how many times I've watched it.