Top 10 Movies Like When Harry Met Sally That You Should Watching Update 10/2021

movies like when harry met sally

A classic of the romance-comedy genre, When Harry Met Sally… These other rom-coms from the last ten years are all of a piece.

In the history of romantic comedies, When Harry Met Sally… stands out as a seminal film. When Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) discover their friendship develops into something more, the movie is credited with introducing a common plotline in the romance genre: the pairing of an aloof man with a needy woman.

Read more: Top 10 Movies Like When Harry Met Sally That You Should Watching Update 10/2021

Several successful rom-coms bear its imprint on their DNA. Here are ten great romantic comedies from the last decade for fans of When Harry Met Sally…to enjoy.

1. Celeste And Jesse Forever (2012)

Celeste And Jesse Forever (2012)

Celeste and Jesse are played by Rashida Jones and Andy Samberg, two high school sweethearts who married after graduation. However, as time passes, their bond grows sour. Even as they begin to date other people, they strive to maintain their friendship.

The screenplay was written by Jones and depicts a couple on the verge of divorcing. When Harry Met Sally… is a formula that has worked for decades, this was Jones and Samberg at their most sentimental.

2. Set It Up (2018)

With the release of Crazy Rich Asians, rom-coms returned to popularity in 2018. Set It Up, a Netflix original film, also fits neatly into the year. An overworked pair of aides (Harper and Charlie, played by Zoey Deutch and Glen Powell, respectively) band together to help out with an impossible task: getting their bosses a date.

It’s all too easy to write this off as just another Netflix rom-com, but the chemistry between Deutch and Powell is what really makes it shine. It also helps that Harper and Charlie have such polar opposite personalities that their banter is always fast-paced, witty, and full of passion.

3. Cyrus (2010)

Cyrus (2010)

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This comedy-drama stars John C. Reilly as a recently divorced man, and Marisa Tomei as a single mother who meets John (C. Reilly) at a party and falls in love with him. The relationship, however, is put to the test when John meets Cyrus, Molly’s son (Jonah Hill).

With its low production value, heavy dialogue, and focus on the characters’ relationships, this film fits the mumblecore mold perfectly. John and Molly’s banter has shades of Harry and Sally’s wit running through it. This is a true gem that is far too often overlooked.

4. Plus One (2019)

Additionally, the story focuses on long-time friends Alice (Maya Erskine) and Ben, both of whom are engaged to be married. They come to an agreement that they will be each other’s partners at every wedding.

Romantic comedies love to make fun of weddings because they are such a tired trope. This idea is central to Plus One, as it’s what brings Alice and Ben together on a platonic level. Erskine and Quaid have a natural chemistry together thanks to their previous work in comedic roles on television.

5. Trainwreck (2015)

Trainwreck (2015)

In recent years, Judd Apatow has produced some of the most inventive romantic comedies. Trainwreck, the Amy Schumer comedy, is one of them. Schumer portrays a driven but impulsive magazine writer who clings to her father’s anti-monogamy beliefs. Aaron Conners (Bill Hader), an eminent orthopedic surgeon, soon wins her heart and she begins a committed relationship with him.

This is Schumer at her most vulnerable and approachable, and as their relationship develops, this strengthens Schumer’s connection to Hader. Trainwreck is raunchily sentimental in its own way, even if it doesn’t subvert the Harry and Sally subgenre.

6. Maggie’s Plan (2016)

Grete Gerwig plays a New School director who wants to get pregnant and raise a child by herself after graduating from the school. However, she finds herself falling in love with John (Ethan Hawke), which throws her plans for revenge into disarray. More people appear in her life, putting her faith in romance to the test once again.

Her free-spirited characters in several mumblecore films have made her a star in addition to her directorial work. With Maggie, she embraces every scene and brings out a natural sweetness that more than makes up for the love triangle plot’s shortcomings with her interactions with John (the third party being Julianne Moore).

7. Top Five (2014)

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Top Five (2014)

This incisive satire on Hollywood and stardom stars and is directed by Chris Rock. He takes on the role of Andre Allen, a stand-up comic who aspires to take on more serious roles. The groom’s fiancee (Gabrielle Union) has other ideas, as she intends to make their wedding a public event. When he meets journalist Chelsea Brown (Rosario Dawson), he finds solace in her company for the day.

Most of the time, this is just another look into the life of a stand-up comedian, with dialogue written by none other than Chris Rock. However, the show’s core is built around the personal interactions between Andre and Chelsea, two people who couldn’t be more different.

8. Crazy, Stupid Love (2011)

A shirtless Ryan Gosling scene may make the movie famous, but the film is primarily about Cal (Steve Carell) and Emily (Julianne Moore) and their post-divorce pursuits after their marriage falls apart. Jacob (Gosling) offers Cal dating advice, while Emily becomes close with coworker David Lindhagen (Kevin Bacon).

In this film, there are echoes of When Harry Met Sally, particularly between Jacob (Jake Gyllenhaal) and Hannah (Emma Stone), whose interactions are awkwardly sweet.

9. Enough Said (2013)

enough-said-2013

Regarding romantic comedies about people going through midlife crises, Enough Said depicts the romance between massage therapist Eva (Julia Louis-Dreyfus) and recently divorced Albert (James Marsden) (James Gandolfini). The more Eva and Albert get to know one another, the more she discovers that Albert is the ex-husband of her poet friend Marianne (Catherine Keener).

This set-up could have led to wacky romantic antics, but the film deals with its subject matter maturely and truthfully.. The blossoming romance between polar opposites Eva and Albert, inspired by director/writer Nicole Holofcener’s own life events, is sincere and endearing.

10. The Big Sick (2017)

Kumail Nanjiani has a lot of great stories to tell, as evidenced by his Oscar-winning romantic comedy-drama, The Big Sick. Nanjiani’s interracial romance with Emily Gordon, a writer, and the issues that arise as a result of Emily’s hospitalization served as inspiration for The Big Sick. Meanwhile, Kumail must deal with both his own and Emily’s families during her recovery (Holly Hunter and Ray Romano).

Fans of When Harry Met Sally… can look forward to this romance delving into the many facets of a relationship between two people who are (culturally) polar opposites from one another. And Nanjiani and Zoe Kazan’s chemistry is contagious, witty, and endearing.

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