10 Best Romantic Comedies of the 1990s

Sep 2, 2010
Leslie C. Halpern

: Four Weddings and a Funeral is a Top Romantic Film - Copyright 1994 Polygram Filmed Entertainment

An intriguing mix of romance, humor, and chemistry make some romcoms stand out from the others as iconic films of the decade.

In the perfect romantic comedy movie, boy meets girl, then loses girl, then gets girl back again. The idealized romantic leads excel either physically, intellectually, spiritually, or some combination of the three. There also needs to be a firmly established time and place in which the characters fall in love that isn’t too overshadowed by special effects or mixed-genre subplots.

The 10 romantic comedy movies below can be broken down into three distinct categories: exotic foreigners, working women, and lonely guys. Although these films represent the best romcoms representative of that time period, they are not the only wonderful date movies from the 1990s. Period pieces, such as Emma and Shakespeare in Love also came out during this time. For more information, read 10 Best Historical Romance Movies.

Romantic Comedies About Exotic Foreigners Searching For A Mate

L. A. Story (1991): A West Coast weatherman falls in love with a British newspaper reporter who is temporarily located in Los Angeles. Iconic status: captured all the quirks of the L.A. lifestyle in the 1990s through a supernatural love story punctuated with unexpected cameo appearances. Starring Steve Martin, Victoria Tennant, Richard E. Grant, Marilu Henner, Sarah Jessica Parker.
Four Weddings and a Funeral (1994): A confirmed British bachelor takes a fancy to a sophisticated American woman whom he meets at a wedding. Iconic status: became the first of several excellent romantic comedy collaborations between writer Richard Curtis and actor Hugh Grant (including Notting Hill, Bridget Jones’s Diary, Love Actually, and Bridget Jones: The Edge of Reason). Starring Hugh Grant, Andie MacDowell, Simon Callow, Kristin Scott Thomas, James Fleet.
French Kiss (1995): A nervous Canadian living in America visits France to retrieve her errant fiancé, but instead finds a new French lover. Iconic status: offers two exceptionally funny performances by the leads, in addition to being released at the height of Meg Ryan’s popularity as the reigning queen of date movies between 1993’s Sleepless In Seattle and 1998’s You’ve Got Mail. Starring Meg Ryan, Kevin Kline, Timothy Hutton, Jean Reno, Francois Cluzet.
Notting Hill (1999): An everyday man (Hugh Grant) who runs a travel bookstore in Notting Hill begins a tentative relationship with an enormously popular international movie star. Julia Roberts plays the famous American actress who seems very much like the real Julia Roberts. Iconic status: it combined America’s sweetheart with Britain’s lovable cad for the first time, and introduced American audiences to Rhys Ifans, who plays the incredibly crude, rude, yet lovable roommate of William Thacker (Grant). Also starring Hugh Bonneville, Richard McCabe, Alec Baldwin, Emily Mortimer.

1990's Romantic Films About Working Women Getting Love As A Bonus

Pretty Woman (1990): A high-priced call girl manages to charm a wealthy businessman during his extended stay in Los Angeles, California, in this rags-to-riches love story. In addition to catapulting Julia Roberts to fame, this film achieved iconic status by pairing two physical beautiful leads with quirky character Hecto Elizondo in a Garry Marshall-directed movie. This same winning combination was slightly less successful in 1999’s Runaway Bride in which the team reassembled for another romantic comedy, but with less-likeable characters. Starring Richard Gere, Julia Roberts, Jason Alexander, Ralph Bellamy, Laura San Giacomo.
Jerry Maguire (1996): A sports agent loses his high-powered job after adopting a new code of ethics and has only a co-worker from the accounting department and one client left who support him. Iconic status: memorable lines such as “Show me the money,” “You had me at hello,” and “You complete me” soon became catch phrases of the 1990s. Starring Tom Cruise, Renée Zellweger, Cuba Gooding, Jr., Kelly Preston, Jerry O’Connell.
You’ve Got Mail (1998): An independent children’s bookseller fights against a chain of national bookstores that threaten to put her out of business. Iconic status: playfully re-unites actors Tom Hanks and Meg Ryan with director Nora Ephron (from 1993’s Sleepless in Seattle). As Kathleen Kelly and Joe Fox, Ryan and Hanks present flawed characters whose charm more than makes up for their inadequacies. Starring Tom Hanks, Meg Ryan, Greg Kinnear, Parker Posey, Steve Zahn.

Best Rom-Coms About Lonely Guys Overcoming Their Loneliness

Sleepless in Seattle (1993): A Baltimore newspaper reporter becomes enamored with a widowed man who tells his sad tale on a radio talk show. The tension builds throughout the entire film as the couple finally meets in the third act. Iconic status: successfully updates 1957’s An Affair to Remember. The music and screenplay were nominated for Academy Awards that year. Starring Tom Hanks, Meg Ryan, Bill Pullman, Rob Reiner, Rita Wilson.
The Wedding Singer (1998): Made in the 1990s but set in the 1980s, this entertaining romantic comedy features interesting cameos, good music, a believable romance, funny dialogue, and some good-natured stabs at '80s culture as a broken-hearted wedding singer looks for love. Iconic status: unlike his earlier comedies in which he played imbeciles, Adam Sandler finally broke through as an intelligent, likeable male romantic lead that was followed by similar roles in the 2000s. Starring Adam Sandler, Drew Barrymore, Christine Taylor, Alan Covert, Matthew Glave.
There’s Something About Mary (1998): In this outrageous romantic comedy, a kind-hearted loser follows his dream girl from Rhode Island to Florida. This film achieved iconic status for two reasons: It boosted Ben Stiller’s career to an A-list romantic lead, and established an audience for Judd Apatow and other next-generation gross-out romantic comedy filmmakers of the 2000s. Starring Ben Stiller, Cameron Diaz, Matt Dillon, Chris Elliot, Lee Evans.