I don't know if it was just the decade, but the 1990's definitely had some good romantic comedies. I am not a huge fan of romantic movies, but give me something with a little humor and I am sold. If you haven't seen some of these, I highly suggest you watch them if you are looking for a light-hearted flick that will leave you sobbing into your pillow as you pet your cat because you know you will never meet a guy as great as Heath Ledger or Tom Hanks.
10 Things I Hate About You (1999)
One of my favorite movies since I was little. If you are looking for a movie that deals with a strong female character dealing with high school and being pestered by the forever beautiful Heath Ledger, this movie is probably for you. Plus, there is a baby Joseph Gordo-Levitt and it's set in Seattle. What more could you want?
While You Were Sleeping (1995)
This is an overall feel good romantic comedy. This movie features a rather adorable Bill Pullman and an odd love triangle that involves a man in a coma. I always watch this movie for a little pick me up. Also, Peter Gallagher's eyebrows make a cameo so you obviously have to watch it.
Never Been Kissed (1999)
This is a movie I am sure a lot of us can relate to. Following the life of a journalist who goes undercover at a high school, Drew Barrymore's character is forced to relive her awful years of high school again while falling in love with an unrealistically attractive high school teacher. Molly Shannon plays her wing woman and Jessica Alba plays a mean girl - it's a win, win.
You've Got Mail (1998)
It's a Meg Ryan and Tom Hanks movie. It's the fucking law to watch it. So do it.
It Takes Two (1995)
This is borderline a romantic comedy, but I am counting it because it does involve a love story. I have an obsession with the Olsen twins and this is my favorite movie they ever done. While it deals an orphan and a child of a rich family, the entire movie is about bringing two people, a millionaire and a lady with child services, together, its great. If you are fan of Mary-Kate acting like a tomboy and sloppy joes, watch it.
Notting Hill (1999)
Anything with Julia Roberts and Hugh Grant, I will watch it. They are both two of my favorite actors and this movie is excellent. With a little spin, this movie follows the love story of a travel book shop owner and a world wide celebrity. It has all of the Hugh Grant humor every movie needs and takes place and wonderful England. If you are a fan of funny supporting characters, you will love Hugh Grant's roommate in this. I do.
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