1. Love Actually

This gem is officially old enough to rent a car—Love Actually turned 20 this year. (Feeling ancient yet?) From the first tear-jerking Heathrow montage to the final love-infused chaos, it’s nine interconnected stories about that wild, wonderful thing called love. Not everyone gets their happy ending, though. Alan Rickman’s character? Oh, we’re still not over that scarf scene.

Pairing: Pinot Noir. Why? Because like the characters in this movie, Pinot Noir is complex, occasionally fragile, and often leaves you emotionally conflicted. Try Styring Pinot Noir, a bottle as classic as Hugh Grant’s dad dancing.

2. The Holiday 

Let’s be honest—this movie is every single woman’s ultimate Christmas fantasy: a last-minute house swap that lands you in a cozy English cottage or an L.A. mansion… oh, and also Jude Law. Two women swap heartbreak for picture-perfect holiday cheer, complete with accidental love stories that make us swoon every. single. time. Let me just say again, someone gets Jude Law.

Pairing: Champagne. It’s all about new beginnings and bubbly endings (hello, New Year’s Eve scene). Don’t blame me if you’re tempted to toast your TV every time Jude smiles.

3. Spirited

This new kid on the holiday block burst onto the scene in 2022, and it’s already earned a permanent spot on my “must-watch” list. A modern musical twist on A Christmas Carol, featuring Ryan Reynolds, Will Ferrell, and more heartwarming laughs than sharing old family stories that no-one gets outside of your family. Add some toe-tapping numbers and a reminder to be a decent human, and you’ve got a Christmas miracle.

Pairing: French 75. Gin + champagne + a dose of “oh, this is strong” = the past, present, and future of festive sipping. Prairie gin adds that modern kick, while the bubbles make it dance-worthy (just like the finale).

4. Elf

No matter how many times I watch Buddy the Elf navigate New York City in his candy-fueled joy, it never gets old. Will Ferrell is chef’s kiss as the overly cheerful elf-human hybrid who melts our hearts while downing syrup-covered spaghetti.

Pairing: A chilled Sancerre. Light, crisp, and refreshing, just like the snowflakes Buddy catches on his tongue. Domaine Vacheron Sancerre Rosé is your winter wonderland in a glass.

5. A Christmas Story

Ah, the timeless charm of Ralphie and his quest for that elusive Red Ryder BB gun. Whether you’re dodging bullies, decoding secret messages, or trying not to shoot your eye out, this 1983 classic delivers laughs and warm fuzzies like no other.

Pairing: A Manhattan. It’s a cocktail as timeless as this movie, with a hint of nostalgia and a touch of sophistication. Sip slowly and let the black-and-white vibes transport you to simpler times.

Honorable Mentions: I know, I know—I skipped Home Alone, White Christmas, and It’s a Wonderful Life. But these five are the ones I watch every year without fail. Feel free to let me know if I’m a cotton-headed ninny-muggins for leaving out your favorite. Cheers to a holiday season filled with laughter, love, and excellent wine!