Best Movie Couples in Romantic Comedy History, Ranked

Everybody loves a good romantic comedy. Over the years, romantic comedies have become one of the most popular and profitable genres in Hollywood by giving audiences hope, making them feel good, and being overall extremely entertaining. Throughout its history, there have been many big rom-com actresses, like Julia Roberts and Jennifer Aniston, as well as irresistible leading men like Hugh Grant and Richard Gere. One of Roberts’ most beloved romantic comedies, for instance, was the 1990 hit Pretty Woman, in which she played the now-iconic Vivian Ward opposite Gere. Roberts even earned a Best Actress Oscar nomination for her performance.

Other classic romantic comedies besides Pretty Woman include When Harry Met Sally, 10 Things I Hate About You, and Clueless, which are still as quotable and lovable as ever. Watching the evolution of the genre and seeing how modern-day values and improvements in technology and society have shifted the way rom-coms are written is also interesting. This year brings new titles to add the list: from Valentine’s Day’s release of Marry Me, starring Jennifer Lopez (and important figure in rom-com history) and Owen Wilson, and Amazon’s I Want You Back to the groundbreaking Bros, which releases in August and, according to IndieWire, will effectively be the first mainstream Hollywood romantic comedy with an entirely LGBTQ+ cast. Until then, here are some of the best romantic comedy movie couples in the history of the genre, ranked.

Related: Best Jennifer Lopez Romantic Comedies, Ranked

10 Simon and Blue — Love, Simon

20th Century Studios

Coming up first on our list for best romantic comedy movie couples is Simon and Blue from the 2018 film Love, Simon. Nick Robinson and Keiynan Lonsdale star as Simon Spier and Bram “Blue” Greenfeld, respectively, in the movie alongside a very talented cast that includes 13 Reasons Why star Katherine Langford and the master of romantic comedies, Jennifer Garner. Love, Simon is available to stream on Hulu Plus and is a beautiful and entertaining love story that everyone should see at least once. More significantly, Love, Simon was the first Hollywood studio romantic comedy that centered a gay love story, making it one of the most groundbreaking movies, on our list.

9 Darius and Nina — Love Jones

New Line Cinema

Larenz Tate and Nia Long are incredible on-screen together in the 1997 romance/drama Love Jones. The two play Darius Lovehall and Nina Mosley, two artists, a screenwriter and a photographer, who fall in love one night after meeting in a Chicago club. The two hit it off and share a beautiful connection only to have the relationship stop to a halt when Nina shares that she is leaving for New York in hopes to mend her relationship with her ex.

8 Jenna and Matt — 13 Going on 30

Revolution Studios

This classic fantasy/romance follows a young girl in junior high who dreams of the day when she can escape the immaturity and annoyances that come with junior high boys. Becoming a grown-up and living in this picturesque world is all Jenna can think about until, suddenly, she finds herself transformed and transported into her 30-year-old self, living in an entirely new reality in the future. Fan favorite and critically acclaimed actors Jennifer Garner and Mark Ruffalo star in the film, making 13 Going on 30 one of today’s most beloved rom-coms.

7 Amanda and Graham — The Holiday

Universal Pictures

Even though this movie is probably best to watch during the wintertime, and during the holiday season, Amanda and Graham’s relationship can be admired all year round. This gorgeous and hilarious couple is played by none other than Cameron Diaz and Jude Law, respectively, who star alongside Oscar-winning actress Kate Winslet and Jack Black. The Holiday follows Diaz and Winslet’s characters Amanda and Iris who are fed up with their day-to-day lives and need an escape from reality. The two end up swapping their homes — one in Los Angeles, the other in England — for the holidays, leading the two down an unexpected journey filled with love, realization, and growth.

6 Cher and Josh — Clueless

Paramount Pictures

Clueless is one of the most iconic and quotable films from the 90s. With lines like “Ugh, as if!” and “She could be a farmer in those clothes,” it’s safe to say this movie is going to be referenced forever. Besides Cher’s amazing one-liners, one of the most unforgettable aspects of Clueless is the witty and charming relationship that builds between Cher Horowitz and Josh, played by Alicia Silverstone and Paul Rudd respectively. Fans instantly became obsessed with the couple and continue to love them today.

5 Hannah and Jacob — Crazy, Stupid Love

Warner Bros.

The on-screen relationship between Ryan Gosling and Emma Stone is one of Hollywood’s favorite pairings. The two lit up the screen together as Jacob and Hannah in Crazy, Stupid, Love alongside Steve Carell, Julianne Moore, and Melissa Tomei. Stone and Gosling give incredible performances and are one of today’s favorite movie couples. They reunited for their most recent and acclaimed roles, Mia and Sebastian in La La Land, which was nominated for 12 Oscars, winning Stone her first Academy Award for Best Actress.

Related: Best Emma Stone Movies, Ranked

4 Vivian and Edward — Pretty Woman

Touchstone Pictures

Pretty Woman quickly became both Julia Roberts and Richard Gere’s most iconic movie. Roberts stars as Vivian Ward, a sex worker living in Los Angeles, who stumbles into a charming and wealthy man named Edward Lewis, played by Gere who is looking for directions. Vivian’s natural charisma and energy shine through the stereotypes that may surround her and the two genuinely hit it off. Vivian is smart, witty, and tough, challenging Edward during each step of their relationship.

3 Mary and Tim — About Time

Universal Pictures

Overall, About Time is a great film that will pull at your heartstrings every step of the way. Rachel McAdams and Domhnall Gleeson star as lovers Mary and Tim in this movie submerged in passion, family, sorrow, love, and the inevitable battle of time. At the beginning of the film, we see Tim discover from his father that all the men in his family have the gift of going back in time. They can re-do and relive moments from their past almost like a second chance. Tim uses this gift to his advantage when he meets the love of his life, Mary. No matter how many times Tim goes back in time, though, he realizes more and more the importance of the present and what a gift life is.

2 Kat and Patrick — 10 Things I Hate About You

Touchstone Pictures

Filled with angst, passion, and high school drama, 10 Things I Hate About You has become one of the most relatable and favorite romantic comedies of all time. The incredible Heath Ledger and Julia Stiles star as Patrick Verona and Kat Stratford, respectively, two edgy and rebellious teens who seem like an unlikely pairing at first but are bound to be together. Joseph Gordon-Levitt and Larisa Oleynik also give great performances in the film as Cameron James and Bianca Stratford.

1 Harry and Sally — When Harry Met Sally

Columbia Pictures

Coming in at number one on our list for best romantic comedy movie couples is Harry and Sally from the iconic 1989 film When Harry Met Sally. From beginning to end, this film is hilarious, playful, and endearing, which is all due to the incredible chemistry between Meg Ryan and Billy Crystal, who give the most memorable performances of their careers. They may fight like crazy and get on each other’s nerves, but in the end, Harry and Sally are meant to be together and are there for one another no matter what. You can currently stream When Harry Met Sally on HBO Max.


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