Cover Drew Barrymore has delivered some of cinema’s most comforting romantic comedies like ‘50 First Dates’ (Photo: IMDB)
Drew Barrymore has delivered some of cinema’s most comforting romantic comedies like ‘50 First Dates’ (Photo: IMDB)
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As Drew Barrymore celebrates her birthday on February 22, revisit the romantic comedies and feel-good films that made her America’s sweetheart
Among the best Drew Barrymore movies are The Wedding Singer (1998), 50 First Dates (2004), Ever After (1998) and Music and Lyrics (2007)—romantic comedies that showcase the actress’ warmth and easy chemistry with co-stars like Adam Sandler and Hugh Grant.
A member of the legendary Barrymore acting dynasty, she became a household name in E.T. the Extra-Terrestrial, later starring in blockbusters like Scream and Charlie’s Angels before cementing her status as one of the defining rom-com leads of the late ’90s and early 2000s. As she marks her birthday on February 22, revisiting her most heartwarming films is a reminder of why she remains a comfort-watch favourite for audiences who grew up with her.
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Why is ‘The Wedding Singer’ (1998) Drew Barrymore’s most iconic rom-com?
Above Drew Barrymore and Adam Sandler in their first romantic comedy collaboration
The Wedding Singer launched Drew Barrymore’s legendary partnership with Adam Sandler, creating one of Hollywood’s most endearing on-screen couples. As Julia Sullivan, a kind-hearted waitress trapped in an engagement to the wrong man, Barrymore delivers pure romantic sincerity opposite Sandler’s heartbroken 1980s wedding singer. Their chemistry feels effortless, culminating in the aeroplane scene where Sandler serenades her with “Grow Old With You”. The New Wave soundtrack and ’80s nostalgia make this the gold standard of feel-good cinema that grossed US$123 million worldwide.
What makes ‘Ever After’ (1998) Drew Barrymore’s best fairy tale?
Above Barrymore reimagined Cinderella as a Renaissance heroine in ‘Ever After’
Ever After reimagined Cinderella as feminist historical fiction, with Drew Barrymore’s Danielle de Barbarac rescuing herself without magic. Released the same year as The Wedding Singer, this Renaissance-set romance showcases breathtaking costume design, including the iconic iridescent “Breathe” gown and winged masquerade dress that became ’90s cinema fashion touchstones. Barrymore grounds the fairy tale in emotional reality, proving that intelligence and strength triumph over circumstance.
Why is ‘Never Been Kissed’ (1999) a cult classic?
Above Barrymore played undercover journalist Josie Geller in her first Flower Films production
Never Been Kissed marked Drew Barrymore’s debut as producer through her company Flower Films, giving her creative control over her career. As Josie Geller, a 25-year-old copy editor going undercover at high school, Barrymore taps into universal fears of reverting to awkward adolescence. The character “Josie Grossie” became a hero for late bloomers everywhere. The romantic climax—waiting on a baseball pitcher’s mound for her first real kiss as The Beach Boys’ “Don't Worry Baby” plays—remains one of rom-com's most definitive moments.
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How does ‘50 First Dates’ (2004) showcase Drew Barrymore’s range?
Above The amnesia rom-com showcased the depth of the Sandler-Barrymore partnership
50 First Dates reunited Barrymore with Adam Sandler for a high-concept Hawaii-set romance about Goldfield’s Syndrome, a fictional form of short-term memory loss. Barrymore faced a unique challenge playing Lucy Whitmore, a woman who wakes up thinking it’s the same day, forcing her to fall in love repeatedly. While Sandler provides comedy, Barrymore anchors the emotional truth. The poignant ending—Lucy waking on a boat, watching a video explaining her life—subverts rom-com expectations, proving love is a daily choice.
Why is ‘Music and Lyrics’ (2007) an underrated Drew Barrymore gem?
Above Barrymore starred opposite Hugh Grant as an aspiring lyricist in this pop parody
Music and Lyrics pairs Barrymore with Hugh Grant as a washed-up 1980s pop star seeking a comeback. As Sophie Fisher, a quirky plant-waterer-turned-lyricist, Barrymore brings surprising musical talent and natural warmth to their creative collaboration. The film’s catchy original soundtrack features the hilariously authentic ’80s pastiche “Pop! Goes My Heart”. Barrymore’s chemistry with Grant transforms formulaic material into genuinely delightful escapism that showcases her gift for playing lovable free spirits.
What role does Drew Barrymore play in ‘He’s Just Not That Into You’ (2009)?
Above Barrymore played Mary in the ensemble comedy about modern dating confusion
In this ensemble exploration of digital-age romance based on the bestselling book, Barrymore plays Mary, a woman navigating MySpace messages and confusing dating signals. Though her role is smaller in this movie, she articulates the exhaustion of modern dating technology with relatable exasperation. Her performance captures millennial confusion about decoding romantic interest through texts and e-mails, making her the voice of a generation struggling with 2000s courtship rules.
How did ‘Blended’ (2014) evolve the Sandler-Barrymore partnership?
Above The third Sandler collaboration focused on blended families and mature romance
Blended marked Drew Barrymore and Adam Sandler’s third collaboration, showing their evolution from young lovers to single parents navigating modern family dynamics. As Lauren Reynolds, a divorced mum on a disastrous blind date that becomes a shared African safari, Barrymore brings maternal warmth and hard-earned wisdom. While less critically acclaimed than The Wedding Singer or 50 First Dates, the film showcases their enduring real-life friendship and comfort with vulnerability, reflecting their journeys into parenthood.
Why does ‘Going the Distance’ (2010) feel so authentic?
Above The bi-coastal romance featured raw chemistry with then-boyfriend Justin Long
Going the Distance benefits from Drew Barrymore’s real-life relationship with co-star Justin Long, infusing this long-distance love story with genuine intimacy. As Erin, navigating a bi-coastal relationship between New York and San Francisco, Barrymore brings improvisational rawness that feels refreshingly unpolished. The film’s honest depiction of modern relationship frustrations and sacrifices, combined with their authentic chemistry, creates a rom-com that feels lived-in rather than scripted—a fitting addition to Barrymore’s rom-com reign.
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After more than a decade in lifestyle media, Clifford has mastered the art of writing seriously about things that are fun—and writing fun things about people who take themselves very seriously. At Tatler Asia, he helped steer its flagship lists, Tatler’s Most Influential and Asia’s Most Stylish. And today, he leads T-Labs, Tatler Asia’s content innovation hub, where he continues the noble pursuit of lifestyle storytelling, spinning stories on wealth, entertainment, necessary style, Hallyu, Hollywood, beauty and more for audiences across Asia.
