TV + Movies

5 Drew Barrymore Movies That Brighten The Dread Of Mid-Winter

When winter has you down, Drew Barrymore can raise you up.

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Drew Barrymore is loved by many. Her movies have such a warm, feel-good energy—perfect for a cozy winter feel-good fix!

50 First Dates 

Drew Barrymore and Adam Sandler in 50 First Dates (2004)

Set in dreamy Hawaii, 50 First Dates is like a little slice of sunshine in the middle of winter. This rom-com follows Henry (Adam Sandler) as he falls for Lucy (Drew Barrymore), only to discover she has short-term memory loss and forgets him every day. It’s heartfelt, funny, and has just the right amount of tropical escapism to brighten up a chilly day.

Ever After: A Cinderella Story

For a cozy, fairy-tale escape, Ever After is a winter must-watch. Barrymore brings charm and strength to this Cinderella retelling, where there’s no magic—just a smart, independent heroine rewriting her own story. The stunning 16th-century French setting, dreamy romance, and gorgeous costumes make it the perfect film to curl up with on a snow day.

Never Been Kissed

Drew shines in this rom-com classic as Josie, an awkward journalist who goes undercover at a high school, reliving her teenage years in all their cringey glory. It’s got romance, humor, and a heartwarming message about self-love and second chances. Plus, that final baseball stadium scene? Still iconic.

The Wedding Singer

Adam Sandler and Drew Barrymore in The Wedding Singer

Another Drew Barrymore and Adam Sandler movie – because together they are always rom-com gold. The Wedding Singer is pure fun, set in the neon-colored, big-haired ’80s. It’s got heart, humor, and a killer soundtrack, plus one of the sweetest grand gestures in movie history. If you’re looking for something warm and comforting, this is the ultimate feel-good watch. 

Charlie’s Angels

If you need an instant energy boost, Charlie’s Angels delivers action, comedy, and major girl-power vibes. Drew Barrymore, Cameron Diaz, and Lucy Liu make the ultimate trio, kicking butt and having a blast while doing it. It’s stylish, over-the-top, and packed with high-energy fight scenes, iconic fashion, and a killer early-2000s soundtrack. Perfect for lifting your mood on a dreary winter day.