When Harry Met Sally ... is one of the defining movies in the romantic-comedy genre. The story about the friendship between Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) which resulted in an unexpected romance was credited for setting the standard for other romantic movies to come and introduced a common plotline in the genre: the pairing of an uptight man with a high-maintenance woman.
Its legacy is marked in the DNA of several successful rom-coms. For this reason, here are 10 of the best romantic comedies from the past 10 years that fans of When Harry Met Sally ... can check out.
Celeste And Jesse Forever (2012)
Rashida Jones and Andy Samberg star as the titular Celeste and Jesse, high school sweethearts who eventually got married. But their relationship turns sour as the years go by. They still try to maintain a constant friendship, even as they begin to see other people.
Penned by Jones herself, the film delves into the period when a romantic couple is on the verge of breaking up. And while it does not innovate from the existing When Harry Met Sally … formula, it showed Jones and Samberg at their most maudlin.
Set It Up (2018)
2018 is the year that rom-coms returned to form with the release of Crazy Rich Asians. And the Netflix film, Set It Up, fits in the same year well. It tells the story of overworked assistants, Harper (Zoey Deutch) and Charlie (Glen Powell), who team up to arrange a date for their bosses.
While it is easy to dismiss this another Netflix rom-com, its main strength is in the chemistry between Deutch and Powell. And the contrasting personalities of Harper and Charlie are good setups for fast-paced, witty exchanges and genuine romantic chemistry.
Cyrus (2010)
From mumblecore auteurs, Jay and Mark Duplass comes this comedy-drama about recently divorced John (John C. Reilly) and single mother Molly (Marisa Tomei), who strike up a relationship after a party. But it gets tested when John meets Molly’s son, Cyrus (Jonah Hill).
This film has all the hallmarks of a mumblecore feature: low-budget production value, heavy dialogue and the examination of each relationship in the film, and there are hints of wit from John and Molly that can be traced back to Harry and Sally. This is just an underrated gem.
Plus One (2019)
Plus One tells the tale of longtime friends, Alice (Maya Erskine) and Ben (Jack Quaid), as they come to terms with the fact that their friends are getting married. They form an agreement to go together as partners from one wedding after another.
Weddings are a heavy cliché that romantic comedies love to poke fun of. Plus One takes this concept as the core element that draw the platonic Alice and Ben together. Having come from comedic roles on TV, both Erskine and Quaid play naturally well together.
Trainwreck (2015)
Judd Apatow has made some of the most innovative rom-coms of recent years. Among them is the Amy Schumer vehicle, Trainwreck. Schumer plays an ambitious but unrestrained magazine writer who adheres to her father’s disbelief in monogamy. However, she soon falls for a well-known orthopedic surgeon, Aaron Conners (Bill Hader), and engages in a serious relationship with him.
This is Schumer at her most personal and accessible, and this makes her rapport with Hader feel natural as their relationship progresses. While it does not subvert the Harry and Sally subgenre, Trainwreck is raunchily sentimental, in its own way.
Maggie’s Plan (2016)
Greta Gerwig plays a New School business director who plans to have a baby and raise it on her own. However, she suddenly falls for John (Ethan Hawke), which complicates her plan. More figures show up in her life, who test her faith in romance.
Apart from directing, Gerwig is known for her free-spirited characters in several mumblecore films. As Maggie, she embraces every scene, and her interactions with John bring out a natural sweetness that makes up for its love triangle scenario (the third party being Julianne Moore).
Top Five (2014)
Chris Rock stars and directs this pointed satire about Hollywood and stardom. He plays Andre Allen, a comedian wanting to do serious roles. But his fiancée (Gabrielle Union) has different plans by making their wedding public. This is when he finds solace in journalist Chelsea Brown (Rosario Dawson), as they spend the day together.
Generally, this is another portrait of a comedian’s life, with the script being pure Chris Rock. But at its heart, it is centered around dthe intimate exchanges between Andre and Chelsea and their contrasting personalities gel.
Crazy, Stupid Love (2011)
Crazy, Stupid, Love may be famous for the infamous scene featuring a shirtless Ryan Gosling, but it is generally a poignant love story about the marriage fallout of Cal (Steve Carell) and Emily (Julianne Moore), and their post-divorce pursuits. Cal gets advice from Jacob (Gosling) on how to pick up women, while Emily bonds with colleague David Lindhagen (Kevin Bacon).
There are some nods to When Harry Met Sally … when it comes to each relationship explored in this film, particularly between Jacob and Hannah (Emma Stone), and their interactions are awkwardly sweet.
Enough Said (2013)
Speaking of midlife crises rom-coms, Enough Said focuses on the romance between massage therapist Eva (Julia Louis-Dreyfus) and recently divorced Albert (James Gandolfini). As their fondness for each other grows, Eva soon learns that Albert is the ex-husband of her poet friend, Marianne (Catherine Keener).
While this setup could lead to wacky romantic antics, this film deals with its subject with maturity and truth. Inspired by the real-life events of director/writer Nicole Holofcener, the growing relationship between polar opposites Eva and Albert feels earnest and sweet.
The Big Sick (2017)
As exhibited by this Academy Award-winning romantic comedy-drama, Kumail Nanjiani has some wonderful stories to tell. The Big Sick is inspired by Nanjiani’s interracial romance with writer Emily Gordon and their problems that arise from Emily’s hospitalization. As she recovers, Kumail must deal with his own family and Emily’s parents (Holly Hunter and Ray Romano).
Fans of When Harry Met Sally … will anticipate how this romance explores many angles when it comes to the relationship of two clear (cross-cultural) polar opposites. And the chemistry between Nanjiani and Zoe Kazan is infectious, witty and adorable.