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

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

Updated 3 days ago, February 17, 2025

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

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

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.