Romcoms are among the most influential movie genres in history. They are popular across all ages, genders, and class backgrounds. They are so influential that they’ve even been known to make the viewers more susceptible to accepting toxic relationship behaviors. While certain romcom characters are indeed red flags, it is still one of the most entertaining genres.

The 1990s were an especially impressive time for romcom movies. Between Nancy Meyers, Garry Marshall, and Nora Ephron, there is a wealth of romcom movies from the 90s. So, we made it our mission to choose and review the three best 1990s romcoms, based on their viewer rating, rewatchability, and how well they’ve stood the test of time.

The Parent Trap

The Parent Trap may not seem like an obvious romcom choice, but it is one of our favorites. The story of twins Hallie and Annie, finding each other at summer camp after being separated at birth, is not usually a romcom foundation. But this Nancy Meyers classic takes us on a ride that is equal parts romantic, hilarious, and heart-warming.

The twins, after meeting accidentally, realize their parents separated them at birth. Thus, they hatch a plan to meet the parent each of them didn’t know. Annie goes to their dad, played by Dennis Quaid. On the other hand, Hallie goes to their mom, played by the late, great Natasha Richardson. Between the hijinks to separate the dad from the evil future stepmother and the schemes to make the parents reconcile, this movie is endlessly entertaining.

The plot line, cinematography, main and supporting cast, and of course, Lindsey Lohan’s performance as both twins make it one of the best 1990s romcoms.

10 Things I Hate About You

There is nothing quite like a William Shakespeare play adaptation into a modern-day romcom. And that is precisely what Gil Junger’s 10 Things I Hate About You is. This 1999 movie was adapted from ‘The Taming of the Shrew’, with the writers deciding to make the setting a Seattle high school. As far as movies based on Shakespeare plays go, it is one of the best ever.

Kat Stratford, played by Julia Stiles, is the grumpy, sarcastic, cynical older sister who doesn’t believe in love. Patrick Verona is the mysterious guy in school whom everyone but Kat fears. Since Kat’s younger sister, Bianca, is only allowed to date if Kat dates, Cameron, who’s crushing on Bianca, hatches a plan. The plan includes paying Patrick to date Kat, but Patrick, in his own words, messes up and falls in love with her.

This movie is a tale of teen romance, angst, self-realization, and friendship, boasting a 72% rating on Tomatometer.

Pretty Woman

Pretty Woman is easily one of the most popular romantic comedies of all time. With two Hollywood heavyweights in Julia Roberts and Richard Gere as the leads, this movie was slated for success. And it did not disappoint. The Garry Marshall-directed masterpiece has earned around $178,500,000 worldwide with a budget of only $14,000,000.

The plot is somewhat of an odd one for a romcom, but the director and the lead actors made it work. Wealthy corporate raider Edward Lewis, hires prostitute Vivian Ward to be his escort to several business and social functions. During their week-long arrangement, the two of them develop feelings. The movie’s grand finale happens when Edward rushes over in a white limo to “rescue” Vivian, as she had dreamed of her entire life.

Pretty Woman may have had mixed critics’ reviews upon release, but 36 years on, it is one of the best 1990s romcoms we’ve ever seen.

A Look Back at the Best 1990s Romcoms

There is no one way to determine the best 1990s romcoms, because everyone’s taste is different. The three movies that we selected certainly stood out to us, but there are dozens, if not hundreds, of others that are just as good. The 1990s were truly a magnificent time for romantic comedies, so you can’t go wrong with any of the options.