Perhaps no other actress has been as heavily associated with the rom-com as Meg Ryan. With her star-making role in 1989’s When Harry Met Sally, the rom-com was elevated to an art form by which all future entries in the genre would be judged.

Her sweet, effervescent personality and her frequent pixie hair cut made her a dream girl for men everywhere during the 90s. Combined with her beauty are her comedic chops, reminiscent of Lucille Ball. For much of the 90s, Meg Ryan was a box-office champion, filling movie theaters with audiences wanting to see an idealized version of love they wished they had.

10 Serious Moonlight – 22%

Directed by Cheryl Hines and written by the late Waitress writer, Adrienne Shelley, Serious Moonlight revolves around an attorney (Ryan) who discovers her husband is about to leave her for a younger woman, so she ducktapes him to a chair in an attempt to persuade him to stay with her.

Serious Moonlight premiered at the 2009 Tribeca Film Festival and then released straight to VOD. Reviews were predominately negative, with many critics noting it pushes the boundaries of “black comedy.” Currently, this is Meg Ryan’s last romantic comedy.

9 I.Q. – 42%

A charming premise, I.Q. finds a mechanic (Tim Robbins), getting coached by the smartest man in the world, Albert Einstein (Walter Matthau), in order to make his brainy granddaughter (Ryan) fall in love with him.

Unfortunately, audiences didn’t fall in the love with the movie. Even actor Tim Robbins was irked by the premise’s aspect of deception. Released to negative reviews, I.Q. was a box-office failure despite coming off the heels of Sleepless in Seattle’s success.

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8 French Kiss – 48%

In French Kiss, Kate (Ryan) has learned her fiance, while in France, has fallen in love with someone else. So, she boards a plane to Paris to win him back. There, she gets help from a French thief (Kevin Kline) and they fall in love.

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Directed by Lawrence Kasdan, French Kiss was the first movie Meg Ryan produced. Intended originally for French actor Gerald Depardieu, ultimately, Kevin Kline took the role, doing a Depardieu impression the whole movie. French Kiss received mixed reviews from critics, with many commending the great chemistry between the two, combined with the picturesque scenery. It was also a box-office success.

7 Kate & Leopold – 51%

Directed by James Mangold, Kate & Leopold is a clever time travel rom-com about a physicist whose ex-girlfriend, Kate (Ryan), falls in love with his great-great-grandfather, Leopold, who’s been brought to the future via a time portal.

Released in 2001, Kate & Leopold would be Ryan’s last successful romantic comedy. Right before the movie’s release, last-minute edits removed the fact that Ryan’s character actually is the great-great-grandmother of her physicist ex-boyfriend. However, the footage was restored for the Blu-Ray release and now is the only version of the film available.

6 Addicted To Love – 55%

The tagline for 1997’s Addicted To Love proclaimed it was about “Two people who get off on getting even.” It revolves around two jilted exes who try to break up their former lovers who are now in a relationship together. However, predictably, they fall in love in the process.

Addicted To Love boasts a very funny script, great performances from Ryan and Matthew Broderick, and a wonderful Rachel Portman score. Unfortunately, critics found the humor “mean-spirited,” and it opened against The Lost World: Jurassic Park, thus, performing well-below Ryan’s then box-office averages.

5 Joe Versus The Volcano – 61%

Teamed for the first time with Tom Hanks, 1990’s Joe Versus The Volcano concerns a terminally ill man who travels to the South Pacific to be thrown into a volcano to appease the island’s natives. Meg Ryan plays multiple roles in the film, but mainly Patricia, a woman who’s literally the “captain of her own ship,” who takes Hank’s Joe to the island. Along the way, they fall in love.

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Written and directed by playwright John Patrick Shanley, the movie received wildly mixed reviews with some calling it one of the worst movies ever made. However, it has since gained a more appreciative cult following over the years.

4 Prelude To A Kiss – 63%

Based on the play, Prelude To A Kiss stars Alec Baldwin and Meg Ryan as a couple, Peter and Rita, whose relationship is turned upside down when Rita’s soul is switched with the soul of an elderly man. The play and film are a metaphor for the  AIDS epidemic at-the-time when very young people affected by the virus seemingly had aged significantly.

The play originally starred Baldwin and Mary-Louise Parker but producers considered Ryan a bigger draw, so Parker was recast. The movie faired poorly anyway, with critics noting Ryan was miscast and that the play just didn’t translate well to the screen.

3 You’ve Got Mail – 70%

In 1998, Tom Hanks reteamed with Ryan for the third time and the result was a winner. While the title and some of the technology discussed in the film are very dated, the concept is fresher than ever. You’ve Got Mail concerns two people who meet in an internet chat room and begin an online romance. The problem is they don’t realize they already know and hate each other.

Written and directed by Sleepless’ Nora Ephron, the movie received largely positive reviews from critics, who praised Hanks and Ryan’s charming chemistry. It was also a huge box-office hit, making it the biggest hit of Ryan’s career.

2 Sleepless In Seattle – 75%

Written and directed by When Harry Met Sally screenwriter Nora Ephron, Sleepless In Seattle reteamed stars, Hanks and Ryan, although they don’t actually meet until the end, and altogether have less than two minutes of screentime together. It concerns a woman who falls in love with a lonely widower she hears on a radio show. She comes to believe they are destined to be together and begins a quest to meet him.

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Considered the ultimate romantic comedy, critics branded Sleepless an instant classic and noted the lead’s great performances. The movie was a huge box-office hit and received a nomination for the Best Original Screenplay Oscar.

1 When Harry Met Sally – 91%

Director Rob Reiner’s When Harry Met Sally is the benchmark by which all rom-coms are measured. Written by Nora Ephron, the movie asks the question “Can men and women truly just be friends?” Ryan and Billy Crystal play two people who, after sharing a road trip together from Chicago to New York, meet several times again as years go on before becoming friends, however that friendship is threatened when they develop romantic feelings for each other.

Released in 1989 against summer blockbusters, word-of-mouth made When Harry Met Sally a surprise hit, garnering praise from the public and critics who proclaimed it funny, touching, masterfully performed, and setting a new standard for romantic comedies to come. Audiences instantly fell in love with Meg Ryan, making her an “American Sweetheart.” The “I’ll have what she’s having” scene at Katz’s Deli has become iconic, along with the rest of the film. It’s now a perennial New Years’ Eve favorite, Valentine’s Day favorite, and a favorite for any day among couples in love, the world over.

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