20 Of My Favorite “Happy Classic” Movies To Help You Escape (Plus My #1 Movie of All-Time)

We all deserve an escape right now with no shame in our Quarantine Game. But then again I’ve never been one to feel guilty about any of my pleasures and happily promote the genius of Outlander and Gillian Flynn books despite knowing that these will never be critically acclaimed. I actually wrote this post 3 years ago but never posted it because why would I publish a ‘my favorite all-time movies’ on a design blog? I’m not a film critic, in fact, quite the opposite. I mostly like entertaining rom-coms and coming of age movies. But these days I need a guaranteed good escape (we all do) so turning to the “happy classics”, as I call them, seems necessary. You’ve probably seen all these movies – they are the movies that when on a plane you can’t NOT watch. The characters feel like friends. You tell yourself you’ll just press play for a second then you find an hour and a half of JOY has passed as you’ve watched Kate Hudson and Matthew Maconahay flirt. So, here it is. My favorite “Happy Classic” movies (with some 2020 updates).

20. Someone Great

This one is more friend love than and dealing with a breakup than anything, but the LOVE is there – it’s just less rom-com and more about female friendship (which is, honestly, equally important). 

19. How To Lose a Guy in 10 Days:

The first time you watch this you’ll be embarrassed by how much you like it. The plot is so cliche and shallow, but they both sell it, you believe in them, and there are some strangely hilarious moments having to do with a tiny yappy dog. It’s become a classic in my book.

18. Always Be My Maybe

Finally a new one from 2019 that is becoming a go-to in the background. Great acting and sweet story. Just talking about it makes me excited to watch it again. 

17. Bad Moms

This is another go-to plane movie while I write posts, not that I’ll be on a plane anytime soon. It seems highly appropriate right now as a lot of us moms might be feeling extra bad (or good?) these days. Speaking of Kristen, a funny post I saw was a mom saying “While homeschooling we need more structure to our day, so tomorrow we are watching Frozen 1 BEFORE Frozen 2”.

16. The Proposal:

It’s practically perfect. Sandra and Ryan are so good, Betty White (and all the other silly character actors) entertain thoroughly and it has enough heart to really root for them the whole way.

15.  Devil Wears Prada:

I worked in the magazine industry in New York in my 20s so this certainly speaks to me, but even if I didn’t I’m sure I would love it. Anne and Meryl kill it, and it has heart, glamour and some hunky love.

14. Set It Up

 I watched this twice in the same week. The two leads have such good chemistry and all the acting is great. I, again, apparently love the “hustling in the magazine industry as a 20 something” genre, but maybe we all secretly do? 

13. Bridesmaids

I can’t. It’s too funny. And has heart with the girl friendship situation. I know you have all seen it, but just watch it again. You’ll be so happy you did.

12. The First Time

YOU GUYS. No one has seen this movie and it’s VERY VERY VERY good, cute and a great one if you are with a partner to watch. It’s a rom-com meets coming of age and those are my two favorite movie genres.

11.  The Notebook

I used to give myself a “1 Notebook a year” allowance for fear that I would watch it too many times and it would lose its specialness (besides the more you watch it, the more flaws you see). I swear I should be a Hollywood trend actor predictor. I KNOW when a male actor is going to hit big time from their first film. I was a fan of his before watching this, too, but after this, I was like THIS GUY WILL SWEEP THE WORLD. Of course, he turned slightly into a D-bag and he’s a bit oversaturated but this movie is still uncomparable on the romance/love-ometer (which is the only meter I care about).

10. Ten Things I Hate About You

’90s angst meets Shakespeare. It’s not particularily amazing but I love when its on TBS. Plus …. Heath.

9. A Lot Like Love

Amanda PEET, Ashton KUTCHER – Visuel de l’Affiche Américaine en Couleur – Color Key Art

How is this not a more popular classic? I LOVE LOVE LOVE LOVE this movie. They have such great chemistry and it’s coming of age in a really fun 2000s kind of way. If you haven’t seen it, please rent it.

8. Definitely, Maybe

He can do no wrong, and while many people think this tale of a movie is cheesy, I for one love watching it over and over. Definitely. Not maybe.

7. Sweet Home Alabama

Pretty much the exact same plot as The Notebook (have you noticed that?) but I’m a huge Josh Lucas fan and I think this movie is entertaining from New York to Alabama.

6. Parent Trap

I was a Lindsey Lohan fan for a long time (and still am, despite her terrible childhood led by unskilled albeit surely loving parents). I love this movie. Not sure why. But it makes me happy.

5. Crazy Stupid Love

YES. UGH. All-star cast, about love and relationships. Emma and Ryan’s love + Steve’s hilariously depressing character makes me smile.

4. The Girl Next Door

This is lesser-known but it is GOOOOOOOD. It’s one of the few romantic comedies that Brian loves as much as I do. This one is about a girl know moves next door to a normal teenage boy, and she is a porn star. It’s not what you think. It’s full of heart and romance.

3. Dangerous Beauty

You are welcome, female America. You are all thinking “what is this movie that I’ve never heard of??” GAH. It’s so good!!!!! I would kill to watch it right now. It’s a sleeper hit (no pun intended) about a courtesan and it is romantic as HELL. It sweeps you away, puts you in the mood and yet makes you feel empowered. WATCH IT.

2. Mean Girls

See. I told you I was a Lindsey fan. And Rachel. And Tina Fey. It’s an obvious classic.

1. Dirty Dancing

That’s right. Dirty Dancing is my #1 movie OF ALL TIME and there is no shame in my Patrick Swayze loving game. And you know what? After I made Brian watch it recently it’s also one is HIS favorite movies. The acting, the production design, the music, the romance – EVERYTHING is so good. And Patrick Swayze truly was a national treasure.

But those are just my “can’t not watch” movies and while I may be able to sneak some time to watch them the next few weeks, even if it’s just on in the background while I write at night, I’d LOVE some new recommendations (or ones that I’ve missed). For instance my team already pointed out that I haven’t seen To All the Boys I’ve Loved Before and I’m so excited to stream it on my laptop while I organize SOMETHING, JUST ANYTHING this weekend. But it’s also been a couple of years since The Notebook so that might be on my agenda as well. Also please don’t forget any “switching bodies’ movies i.e. 13 going on 30, 17 again, The Change Up, etc. Also, I can’t believe I didn’t put Good Will Hunting up there, not because it’s a good rom-com, but Matt and Ben’s friendship makes me really happy. Ok gotta stop, now you please start – what are your “Happy Classics” for all of our no guilt escaping right now???

Fin Mark