15 Feel-Good Movies I Watch Over & Over Again

Project 365, Day 72/365

This title here would suggest that I only have a roster of 15 movies I watch over and over again. That would be incorrect. It took so much self-control not to populate this list so long, you’d still be reading it clear through next Thursday. I’m one of those people who gravitate to old favorites both in terms of television and movies, while Charles always wants to watch and experience something new. You can imagine how fun it is to decide what we’re watching, yes? But forget him, because he’s not part of this story and has nothing to do with this list. File this list away if you happen to share my taste in screen time and draw a blank often when it comes time to watch something that makes your insides feel like a warm chocolate chip cookie (up to you if that comes with a cold glass of milk or not).

Also, I should note, that this list might as well be called “All the Nora Ephron and Nancy Meyers movies I like to watch on repeat,” so there’s that…

Julie & Julia

Julia Child. Meryl Streep. Nora Ephron. Cooking. Paris. Stanley Tucci. Blogging. Zero to hero storylines. I mean…this movie has it all in my book. It’s absolutely one of my favorite movies. I also have the wonderful memory of going to watch this with my mom one Saturday afternoon, and we both loved it so much, she still brings it up sometimes. ::heart swell:: I’d be lying if part of Project 365 didn’t come from a Julie & Julia watch late last year. Who could blame me?

You’ve Got Mail

To me, this movie is magic. Someone could dare me with a big sum of money to never watch this movie again in my life, and I’d probably fail. It’s one of my ultimate “feel better no matter what” movies to turn to. In a good mood? You’ve Got Mail. In a bad mood? You’ve Got Mail. Sad and forlorn? You’ve Got Mail. Movie panacea, I tell ya. At least once a week, I wipe away a rogue tear from Charles’ face (he’s not crying, his eye just does that) and say “Don’t cry, Shopgirl” and feel so pleased with myself. He’s so used to it, it doesn’t even phase him anymore.

Sleepless in Seattle

Okay, okay, I know Sleepless in Seattle and You’ve Got Mail are basically like trying to pass off Pepsi and Coke as wildly different drinks. But they both have their merits and absolutely belong on this list. Newspaper reporter falls in love with an architect over the radio? It checks all the boxes of my life…except I was a magazine editor, and Charles and I met in high school. I mean…it’s pretty close though, yes?

Pitch Perfect

Oh, how I love a good singing movie. I like Anna Kendrick the more I watch her, and Pitch Perfect has a lot to do with that. I 100% cry every single time I watch the final performance (and don’t get me started on the final performance of Pitch Perfect 2 when all the past Barden Bellas come on stage and people start waving their cell phones in the air…completely unrealistic but I care nothing about that).

Never Been Kissed

Show me a movie with the main character reading a grand gesture newspaper article/magazine article/blog article as one of the final scenes, and I’ll show you a movie I love. Is it completely creepy that Drew Barrymore’s high school teacher falls in love with her even when he thinks she’s 17 years old? Oh, truly. But I’m choosing to look past that for the sake of my nostalgia.

Love, Simon

This is a new addition to my list, and it likely has to do with the circumstances around when I watched it, but it’s a sweet movie nonetheless. I was on my way to Florida to spend the week and in the process of interviewing for a new possible job that would have taken Charles and me to Atlanta. I was very excited about the opportunity (that didn’t pan out) and I did the thing that I tend to do, which is to watch every single movie set in a place I’m either about to be or just came from. Love, Simon is set in Atlanta, and I watched it on the plane (another recipe for cementing a movie love with me…something about the dry air??). Anyhow, I just adored it, a high school student grappling with coming out as gay, finding an anonymous pen pal that he fell for without knowing who they were apart from being another high school student grappling with coming out as gay. It’s just lovely, and clearly, I have a movie type.

10 Things I Hate About You

I can remember the first weekend I watched this. I borrowed the DVD from my friend (pretty sure it was a Blockbuster rental if that places it in time for you) on a Friday night. Then I preceded to re-watch it on Saturday afternoon, and I’m pretty sure Sunday had a third watch before I handed it back to her. A young Joseph Gordon Levitt was always more intriguing to me than Heath Ledger, and I was pretty alone in that at the time. ::shrug::

The Secret Life of Walter Mitty

This is a sleeper hit of a movie. If you want to feel like you need to shake the staleness out of your life and really learn to live, watch The Secret Life of Walter Mitty. It’s so, so, so good. It’ll make you want to quit your job and go on an adventure, which is either a good thing or a bad thing (probably a bad thing?).

Sister Act 2

I mean…come on. Solid gold here. There’s not much to say besides a young Lauren Hill singing like a friggin’ angel and one of the best “final performance” sequences in cinematic history (okay, so my nostalgia may be exaggerating my memory of this, but I’m not taking back that sentence because I mean it).

Now & Then

A beloved movie for me growing up, and rewatching it as an adult…it holds up. I remember seeing Christina Ricci’s Roberta duct taping her growing her chest and thought “wow, what a great idea!” I never did do it, but grappling with a quickly changing body, a body that changed WAY faster than most around me, I really saw myself in her.

Crazy, Stupid, Love

Top 10 for me, for sure. Steve Carell is so good in this movie, as is Ryan Gosling. I really love the character development, and look, I’ll never say no to a makeover scene…like ever. Oh, shoot, I’m just not realizing I forgot to add La La Land to this list…let’s just lump it in here, since Emma Stone and Ryan Gosling are in both and great together.

It’s Complicated

My love of Meryl Streep knows no end. I’m definitely not alone on this one, I’m sure. On top of that, show me a Nancy Meyers movie that makes you go “BLEGH THIS MOVIE IS SO UGLY AND GROSS.” IMPOSSIBLE. The set design is perfection, of course, and the cocktail of Meryl with Steve Martin and Alec Baldwin is hard to resist.

Something’s Gotta Give

Fear not. Meryl Streep does not hold my full heart when it comes to protagonists. Diane Keaton falls so, so close to MS. Our beloved Diane is a bit hysterical in this movie, but I find it quite endearing regardless. Not to mention the fact that I often envision myself living in Erica Barry’s Hamptons beach house, sitting at her desk, writing a novel or play or script, then taking a chilly beach walk, wrapping myself in a cardigan dramatically the way women do in movies when they’re cold looking out to a lake or the ocean.

Mamma Mia!

I’m currently listening to ABBA on Spotify. I can thank my mother for my love of the Swedish group, growing up constantly hearing her belting Dancing Queen and Chiquitita (her favorite to sing to her girls). So, of course, Mamma Mia! makes my list. But it’s also just such a fun, sweet movie, and the backdrop of the heavenly Greek Isles certainly doesn’t hurt its cause. And also #MerylStreep.

Crazy Rich Asians

Another stunning backdrop, this time in Singapore. I like the mix of heart, comedy and visual beauty in this movie. Not to mention the fully Asian cast. How refreshing. As someone who is not crazy rich or Asian, it’s a delight to take in someone else’s (made up) life that’s so different from my own.

Yes, by the time I made it to the bottom of this list, I had another 15….50 movies at top of mind, but I’ll leave it for another time. Any feel-good, watch-anytime-always-and-forever movies on your list to share?

See you tomorrow, friends.