We all watch movies, and which is the “best” is a matter of opinion really. Here are the top 10 romance movies from 1990-2000. Don’t forget to check out other lists throughout Thought for Your Penny.
10. Pretty Woman (1990) 61% at Rotten Tomatoes
Edward Lewis is rich and good looking enough to get whoever he wants, except that he’s too focused on his career for that to actually happen. So he hires a hooker for a week to be his arm candy to close a deal. They fall in love and live happily ever after.
Director: Garry Marshall
Starring: Richard Gere, Julia Roberts, Jason Alexander
9. 10 Things I Hate About You (1999) 61% at Rotten Tomatoes
Bianca Stratford wants to date, but her hard-nosed father won’t let her unless her shrew sister Katarina dates too. So Cameron tricks Joey into hiring Patrick Verona to date Katarina. It’s an updated version of Shakespeare’s Taming of the Shrew, and one of the best movies of Ledger’s career.
Director: Gil Junger
Starring: Julia Stiles, Heath Ledger, Joseph Gordon-Levitt
8. Clueless (1995) 81% at Rotten Tomatoes
Cher is determined to help Tai become popular, although it starts to backfire when the popularity goes to her head. She’s a bit superficial, but still with plenty of charm and good intentions. This is the movie that defines everything about 90s pop culture.
Director: Amy Heckerling
Starring: Alicia Silverstone, Britney Murphy, Stacey Dash
7. My Best Friend’s Wedding (1997) 88% at Rotten Tomatoes
Best friends Julianne and Michael have a marriage pact that’s about to expire. She doesn’t want to, until she realizes he’s about to marry someone else. Now she’s on a mission to stop the wedding of her best friend so she can have him to herself.
Director: P.J. Hogan
Starring: Julia Roberts, Cameron Diaz, Dermot Mulroney
6. Titanic (1997) 94% at Rotten Tomatoes
Jack is a poor artist who manages his way onto the inaugural cruise of the storied Titanic ship, an unsinkable luxury liner. On it, he falls for Rose, an upper-class teenager whose mom has plans for her to marry a wealthy aristocrat. The love triangle is interrupted when the ship hits an iceberg and starts to sink.
Director: James Cameron
Starring: Leonardo DiCaprio, Kate Winslet, Billy Zane
5. Can’t Hardly Wait (1998) 40% at Rotten Tomatoes
The senior class is ready to party after graduation, but Preston is obsessed with telling his crush Amanda how he really feels about her. It’s a coming-of-age tale about teenage love that’ll have you hooked from start to finish.
Director: Harry Elfont, Deborah Kaplan
Starring: Ethan Embry, Jennifer Love Hewitt, Seth Green
4. Joe vs The Volcano (1990) 62% at Rotten Tomatoes
Joe works at a horrible company until he’s diagnosed with an incurable disease and heads to the island of Waponi Woo to appease the gods by jumping into a volcano. Along the way, he meets a colorful cast of characters and learns about love, life, and destiny.
Director: John Patrick Shanley
Starring: Tom Hanks, Meg Ryan, Abe Vigoda
3. Romeo + Juliet (1996) 72% at Rotten Tomatoes
The Montegues and Capulets are feuding, but young Romeo and Juliet fall in love anyway. It’s a classic Shakespeare tale updated for the modern age with an artistic flair that’s never been seen before. Although you know they’re ultimately doomed, you can’t help but getting attached to the young lovers.
Director: Baz Luhrmann
Starring: Leonardo DiCaprio, Claire Danes, John Leguizamo
2. Ghost (1990) 74% at Rotten Tomatoes
After his murder, a young man teams with a reluctant psychic to warn his artist lover of her impending doom. Soon, he’s fighting the goons of his old business partner while reconnecting with a lost flame. Also, it has the most famous pottery scene in movie history.
Director: Jerry Zucker
Starring: Patrick Swayze, Demi Moore, Whoopi Goldberg
1. Sleepless in Seattle (1993) 72% at Rotten Tomatoes
After moving from Chicago to Seattle, a widower’s son convinces his dad to pour his heart out on a radio talk show. Several women fall in love with him after hearing the show, including Annie, who’s already engaged to a man she knows isn’t right for her. Their long-distance relationship grows over time in this classic movie romance.
Director: Nora Ephron
Starring: Tom Hanks, Meg Ryan, Ross Malinger