36 Comfort Movies To Watch During The Holidays

Comfort Movies To Watch During The Holidays

I can’t ignore the irony that is 2020: what an awful, difficult year, I can’t wait for it to be over – and yet I can’t believe it’s going by so fast. Gretchen Rubin said it best when she said the days are long, but the years are short.

The years are short indeed – not this list though. This list is pretty long.

It’s officially time for some comfort movies, and as personal victims of 2020, we deserve it more than ever. Will this be a holiday in lockdown? Are we headed for a literal home alone Christmas? The answer frightens me, so let me put away the thought like a proper adult and go on pretending everything is fine. I’m suspending reality for the time being. You’ll find me stuck somewhere between a snowy Chicago evening and a rainy New York day, having sundaes at Serendipity or trying to heave a tree up to my second floor apartment through the window.

So here are 36 comfort movies to watch during the holidays. Please keep in mind these are not just any regular movies. They are timeless classics. They are cosy like a warm blanket on a rainy day.

While You Were Sleeping

One of the best feel good movies of all time.

Home Alone

Every damn year. Never gets old.

One Fine Day

More like chaotic day, but what a charming, feel good movie! I’ve lost count of how many times I’ve watched Michelle Pfeiffer and George Clooney banter and fall in love in a rainy NYC.

You’ve Got Mail

Nora Ephron. Need I say more?

Sleepless In Seattle

Another Meg Ryan/ Tom Hanks/ Nora Ephron classic.


Will Ferrel is so hilarious, I don’t even care about the plot. Watching a middle aged man dressed up as an elf behaving like a hyper little kid is enough to crack me up every single time. (Am I.. okay?)

Edward Scissorhands

A gothic romantic fairytale? Such a classic.

About A Boy

Honestly, I cannot resist a Hugh Grant romantic comedy. Nobody can, right? It’s like humanly impossible?

When Harry Met Sally

Rob Reiner has given us some of the best stuff out there – Stand By Me! The Princess Bride! – and directing a Nora Ephron screenplay? An instant classic.

The Holiday

What are the chances of me getting to swap homes for the holidays with a Hollywood celebrity?

It’s A Wonderful Life

A holiday staple. A wholesome classic.

About Time

I’ll watch anything by Richard Curtis and About Time is seriously one of the sweetest, most endearing movies ever.

Julie & Julia

So delightful, so visually satisfying. There’s never too much butter, too much Paris or too much Meryl Streep and Amy Adams.

Notting Hill

So iconic. Ugh.

That Thing You Do!

The soundtrack alone makes it worth it.

What A Girl Wants

Amanda Bynes cracks me up. Such a lovely movie. And it’s set in London – that’s all I have to say.

The Princess Diaries

A teen movie staple.

Mrs. Doubtfire

It just gets better over time.

The Big Sick

A typical, lovable rom-com – except it’s a real story. And how wonderful is that.

Bridget Jones’s Diary

I could never get sick of Bridget and her London misadventures.

13 Going On 30

Thirty flirty and thriving!

High Fidelity

Watch the movie, but also READ THE BOOK. Nick Hornby’s witty writing is absolutely wonderful.

Set It Up

The millennial rom-com we’ve all been waiting for.

Legally Blonde

“What, like it’s hard?”

My Big Fat Greek Wedding

A 2000s gem.

She’s The Man

Once again, Amanda Bynes is hilarious and makes the kind of movies you’ll want to watch over and over again.

The Wedding Singer

Whenever Drew Barrymore and Adam Sandler get together you know it’s gonna be good.

Dead Poets Society

Beautifully directed, a baby-faced Ethan Hawke, another brilliant performance by Robin Williams. O Captain! My Captain!


As if! Iconic.

10 Things I Hate About You

The soundtrack! The performances! Another gem. Hey… your eyes have a little green in them.

The Devil Wears Prada

It’s not just me. John Krasinski is also obsessed with the movie.

Big Daddy

Sentimental and sweet. And so funny.

Little Miss Sunshine

A delightful, bittersweet comedy about families and dreams. Hilarious and heartfelt.

Never Been Kissed

A Drew Barrymore high school classic.

Ruby Sparks

So underrated. Wonderful writing and great performances.

Just Friends

Dorky high school kid turned handsome and successful is back in his hometown... 
we've heard this one before, but Anna Faris and Ryan Reynolds make it absolutely hilarious.

What's your favourite feel-good movie? I'd love to know!

36 Comfort Movies To Watch During The Holidays

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