The Best Of: Comfort Films I Could Watch Again and Again

Re-watching films is something I do more often than I care to admit. When it comes to my film watching habits I am definitely a comfort watcher, I’m not great at keeping up with new releases. In recent months I have been watching more new releases, but I know I will always go back to these films as they are some of my absolute favourites. 

When planning this post I realised that a lot of my comfort films come from my childhood, which isn’t a surprise really as nostalgia is one of the best feelings. All the films mentioned here are ones I’ve seen at least four times (ten times that for the older releases) and they are the films I like to put on when I don’t know what to watch or if I’m having a bad day. 

Anyway onto my top 5 comfort films I could watch again and again.

She’s The Man (2006)

I actually can’t tell you how many times I’ve seen this film. I’ve probably watched it at least once a year since it came out and I’m really in the mood to watch it again soon. I honestly don’t think I will ever get bored of She’s The Man and the fact that I quote it on a daily basis is a true testament to that statement. 

I don’t know if this film would be released these days, is it very un-pc. Maybe? But it’s a huge part of my childhood and honestly, it is absolutely hilarious. If you’ve never seen this film you absolutely need to.

Synopsis: When Viola’s football team is dissolved and she is not allowed to play on the boy’s team either, she disguises herself as her twin brother and participates in the tournament.

Starring: Amanda Bynes & Channing Tatum

Where to watch: Netflix

The Parent Trap (1998)

I’ve been obsessed with this film ever since I was a kid and I still love watching it to this day. As a kid, I genuinely thought Lindsay Lohan had a twin and when I found out she didn’t it blew my mind. 

I was absolutely desperate to go to the summer camp which isn’t something we really have in the UK. Which was unusual as I was very much a stay indoors and read type of kid (I still am). 

The pure nostalgia I feel every time I watch this film cannot be beaten and nothing else will ever come close.

Synopsis: Identical twins Hallie and Annie are separated after their parents’ divorce. Years later, they discover each other at a summer camp and decide to switch places in an effort to reunite their parents.

Starring: Lindsay Lohan, Natasha Richardson, Dennis Quaid 

Where to watch: Disney+

Photo by JESHOOTS.com on Pexels.com

13 Going On 30 (2004)

This is another film I have watched an unholy amount of times. Looking back I was potentially a bit too young to watch this when I saw it for the first time, however, it was something my sister and I bonded over. 

The concept of this was wild to me as a kid. A thirteen-year-old finds themself in an adult body with a cool apartment and their dream job, absolutely crazy. However, I won’t lie to you and say I wasn’t (and still am) completely jealous. The job part, not being thirty at thirteen. 

Synopsis: Jenna Rink makes an unusual wish on her birthday. Miraculously, her wish comes true and the 13-year-old Jenna wakes up the next day as a 30-year-old woman.

Starring: Jennifer Garner & Mark Ruffalo

Where to watch: unfortunately this isn’t available to stream ‘free’ on any platforms but you can rent or buy it from Prime Video or Apple TV

To All The Boys I’ve Loved Before (2018)

I can’t really explain why this film is on this list. For some reason, there’s just something about it that is so comforting to me. This is the most recent addition to my comfort film collection and if you look at the rest of this list the most recent before this was from 2006 which is just wild really.

I’m currently (very slowly) reading the book for the first time but I’m honestly finding it so hard to get into. 

The films, however, I could watch a million times. Peter Kavinsky has me in a chokehold and my god do I love Noah Centineo in this film. This is weird because outside of this series I don’t find him that attractive, but Peter Kavinsky you have my heart.

Synopsis: Lara Jean writes secret, soul-baring letters to her five crushes, but never meant to send them. Now they are out and wreaking havoc on her life.

Starring: Lana Condor, Noah Centineo, Anna Cathcart

Where to watch: Netflix

The Princess Diaries 2: Royal Engagement (2004) 

Another classic from my childhood that I have seen hundreds of times. Not sure if it’s controversial to like the second film more than the first, but come on Chris Pine is in this one! The enemies to lovers trope is immaculately done here and honestly, the entire film is just *chef’s kiss*

I get a real sense of escapism with this film and the idea of being told you are actually a princess and then a year later you find out you’re going to be queen is pretty incredible. Like most young girls at that time the idea of being a princess was magical and finally getting to see Genovia after hearing about it in the first film was incredible. 

I am very, very tempted to watch this film at some point this week as I’m in a real need of a pick me up and what better way to do that than watch one of your comfort films? 

Synopsis: Princess Mia faces a new dilemma when her coronation is stopped by Viscount Mabrey, a scheming nobleman, as the rules state that an unmarried woman cannot be made the queen.

Starring: Anne Hathaway, Chris Pine, Julie Andrews

Where to watch: Disney+


Let me know some of your comfort films in the comments or if yours is featured here!


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