4 Romantic Comedies To Watch If You Love Drew Barrymore

Drew Barrymore is a Hollywood treasure. After being born into an acting family in 1975, a life in the spotlight seemed inevitable.

However, the youngster was thrust into superstardom when she was just seven years old, thanks to her breakout role as Gertie Taylor in 1982’s E.T. the Extra-Terrestrial. Sadly, the glare of the spotlight was too much for a child star to endure and resulted in hard partying and several stints in rehab by the time she was 15. 

Barrymore went on to reinvent herself, proving that she was a resilient human being as well as a talented actress. Over the years, she has starred in some of the biggest comedy films to grace the silver screen, solidifying her place as a legend in entertainment. Her effervescent personality made her a popular leading lady who comes across as super relatable. It’s no wonder that folks always find themselves rooting for her characters. Here are some of her best ones.

The Wedding Singer (1998)

The Wedding Singer stars Adam Sandler and Drew Barrymore in their first on-screen pairing. Set in the 1980s, the story follows small-town wedding singer Robbie Hart (Sandler), who befriends a sweet and quirky waitress named Julia Sullivan (Barrymore). While talking about their upcoming nuptials to other people, Robbie promises to sing at Julia’s wedding to Glenn. But when Robbie’s fiancée Linda leaves him at the altar, he becomes disillusioned with singing. 

Somehow, Julia convinces Robbie to help plan her wedding. While Robbie initially puts his dislike for Glenn aside, he becomes angry after learning that he constantly cheats on Julia and plans to continue this behavior after they’re married. As their friendship grows stronger, Julia and Robbie start to develop romantic feelings for each other. But things get complicated thanks to a bunch of silly misunderstandings and crossed wires. 

Never Been Kissed (1999)

Never Been Kissed follows 25-year-old copy editor Josie Geller (Barrymore), who hopes to advance her budding journalism career at the Chicago Sun-Times. Despite being slightly insecure, Josie is excited when her boss tasks her with going undercover as a high school student to write an expose on local teenage life. But returning to high school proves challenging for Josie, who immediately regresses into her old awkward adolescent self. 

Although she manages to make one friend, it is not enough for her article. After a rival newspaper scoops her story, Julia gets some help from her brother Rob (David Arquette) to boost her popularity and get noticed by the in-crowd. Josie slowly becomes caught up in the charade and struggles to maintain her journalistic integrity. While confronting unresolved issues from her past, she also finds herself falling for her English teacher, Sam Coulson (Michael Vartan).

Duplex (2003)

Duplex sees Barrymore team up with Ben Stiller in a hilarious tale about the worst neighbor imaginable. The story follows Alex Rose (Stiller) and Nancy Kendricks (Barrymore), a young couple who are searching for their dream home in Brooklyn. One day, they stumble upon the perfect brownstone duplex that houses the elderly Mrs. Connelly (Eileen Essell). Believing that her advanced age will make her a quiet neighbor, the couple decides to buy the entire building. 

But they soon discover that Mrs. Connelly is extremely active. She loves watching television at the highest volume and frequently rehearses with her brass band. As a result, Alex struggles to meet his writing deadlines, and tension between the couple and their upstairs tenant escalates. Alex and Nancy resort to drastic measures to force her to move out, but their often outlandish plans backfire with hilarious results. 

50 First Dates (2004)

Set in Hawaii, 50 First Dates follows marine veterinarian Henry Roth (Adam Sandler), who falls in love with an art teacher named Lucy Whitmore (Barrymore) at a local café. They have an instant connection, but the only catch is that Lucy suffers from short-term memory loss, which causes her to forget everything that happened during the day’s events by the next morning. As a result, Lucy is stuck reliving Sunday, October 13, over and over again. 

To spare her from the trauma of her condition, which is due to a horrific car accident, her father, brother, and locals go along with the charade. Despite her protective family and friends’ initial skepticism, Henry comes up with creative ways to meet Lucy each day. Their relationship takes an unexpected turn when Henry decides to create a videotape explaining her condition.