Drew Barrymore’s Best Rom-Coms, Ranked

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A versatile actor with over 45 years of acting experience, we take a look at the best rom-com performances from Drew Barrymore.



Drew Barrymore has been acting most of her life. She began acting shortly after she was born, first appearing on screen in a commercial starring a dog in the 1970s when she was a baby. When she was just six years old, Steven Spielberg cast her in the classic film ET Her career took off.

Throughout her career, Drew Barrymore has won numerous awards for her performances. She has appeared in many commercials, TV shows and films spanning many genres from horror and coming-of-age to sci-fi and romantic comedy. During her 45+ year career, Drew Barrymore has done it all.

Here are seven of the best Drew Barrymore romantic comedies, ranked.

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7 Mixed (2014)

Mixed is a 2014 rom-com starring Drew Barrymore, Adam Sandler, Terry Crews and Kevin Nealon. Adam Sandler and Drew Barrymore end up together at a family resort. They are both single parents, and as their romance blossoms, their children are reaping the benefits of their blossoming relationship. Adam Sandler and Drew Barrymore have collaborated on several romantic comedies beginning with The Wedding Singer in 1998. Blended is a fun family film and has been nominated for several awards.


6 Music and Lyrics (2007)

music and lyrics is a romantic comedy starring Hugh Grant and Drew Barrymore. The story follows a former musician (Grant) as he prepares for his comeback tour. After struggling with writing lyrics, he teams up with Sophie (Barrymore) to become a writing duo and pen a new pop hit within days. Though Grant and Barrymore didn’t work together until 2007, their friendship dates back much further. In 1995, she wrote the actor a letter to help him through a difficult time. The 2007 film was nominated for six awards.

5 Bad Luck (2004)

Height is a 2004 rom-com based on the Nick Hornby novel starring Jimmy Fallon and Drew Barrymore. The film was nominated for nine awards and follows Lindsay’s (Barrymore) new relationship with Ben (Fallon), who seems more interested in his relationship with the Boston Red Sox. Their relationship is going well until baseball season starts and Lindsey realizes how obsessed Ben is with the relationship. Nick Hornby says story is based on his life and football obsession.


4 Never Kissed (1999)

Unkissed Stars Drew Barrymore, Molly Shannon, Michael Vartan, David Arquette and Jessica Alba. The story follows Josie (Barrymore), a journalist who enrolls in high school to do research for her next story. Josie was a geeky nobody when she first entered high school, so this is her chance to shine and become popular, to make sense of history, get a second chance, and build her confidence. David Arquette and Drew Barrymore both won Blockbuster awards for their roles in the 1999 romantic comedy.

See also: Drew Barrymore’s Best Horror Movies, Ranked

3 He’s Just Not That Into You (2009)

He’s just not that into you is a star-studded romantic comedy that tells several interconnected stories about love and dating. The cast includes Jennifer Aniston, Ben Affleck, Scarlett Johansson, Ginnifer Goodwin, Jennifer Connelly, Bradley Cooper and Drew Barrymore. He’s just not that into you shows many relationships at different levels of seriousness and how each couple navigates through the ups and downs. Covering everything from heartbreak to first dates, this film resonates with audiences everywhere. You’ll find lots of fun, nostalgic references to old technologies, like answering machines, Myspace, and dating via email.

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2 The Wedding Singer (1998)

Their first romantic comedy together, The Wedding SingerStars Drew Barrymore and Adam Sandler. The Wedding Singer follows Robbie (Sandler), a wedding singer, and Julia (Barrymore), a caterer. They’re engaged – just not to each other. The film follows Sandler’s character as he falls in love with Juliet. Considered one of the best romantic comedies of the 1990s, the film was later adapted into a Broadway musical that ran for about eight months.

1 50 First Dates (2004)

50 first dates is another collaborative film for Drew Barrymore and Adam Sandler and tells the story of the relationship between Henry (Sandler) and Lucy (Barrymore). The two have an incredible first date and everything is going well until the next day when he realizes that Lucy doesn’t remember him due to short term memory loss. When Henry finds out, he spends the summer taking her on first dates over and over again, trying to get her to remember him. 50 first dates is considered one of the best romantic comedies of the early 2000s.

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