Go-To Comfort Movies

Photo by Ash Fuentes

By Ash Fuentes

I always say that I don’t have time for myself anymore and use that as the reason why I haven’t really watched any new movies lately. With school, work, and contributing to Kindergarten Mag being my top priorities, I’d say I’m pretty busy these days! In reality, I don’t really have any excuses. I actually do have time to tackle my extremely long watchlist that has been begging for attention for years, I just choose to spend my free time rewatching the same movies over and over again.

Most of these movies I discovered when I was younger, which is why most of them are coming of age or take place in high school. I admit, I’m kind of done hearing about high schoolers because the era has now passed and it’s time to move on into better days, but these movies I can’t get rid of. Here are a handful of comfort films that I’ll never get tired of watching and I hope you’ll enjoy!

Clueless (1995) dir. by Amy Heckerling

Okay, so, it may be a little weird that ex-step-siblings end up together but a modern adaptation of Jane Austen’s Emma couldn’t have been done any better. Amy Heckerling made this iconic film ageless. The colorful 90s fashion is always referenced as inspiration for so many styles today, making Cher Herowitz (Alicia Silverstone) a well-known character. There are so many relatable moments throughout the movie as the humor still holds up well. Clueless and Paul Rudd both will never get old.

10 Things I Hate About You (1999) dir. by Gil Junger

I promise that when I say I’ll never get tired of this movie, I really mean it. Adapted from William Shakespeare’s The Taming of the Shrew, this upbeat coming-of-age high school film has the most clever allusions to mix Shakespeare and the 90s. It’s amazing how many easter eggs and hidden gems are written into every detail. The fashion is the perfect blend for late 90s and early 00s kids to bond over. I can’t emphasize how badly I wanted to dress like the main cast. Also, Kat Stratford (Julia Stiles) was a major influence on what type of person I wanted to be. Some may say she was an intimidating rude bitch, but I saw her as witty, strong, and independent. 

Legally Blonde (2001) dir. by Robert Luketic

Elle Woods (Reese Witherspoon) is a great character for women to look up to. She doesn’t sacrifice femininity and act differently than “most girls” in order to achieve such impressive accomplishments. I love how she was written to already be confident and secure in the way she carried herself while her growth was mainly focused on her work ethic and skills. She is naturally just a powerful leader and talented person, but it was obvious how much of a hard worker she was. I think it’s impossible to get bored of rewatching this movie because of how relevant it remains. If you ever need motivation in anything in your life, put this movie on!

A Cinderella Story (2004) dir. by Mark Rosman

Sam (Hilary Duff) is an odd character. She is the person you want to be while watching the movie because she’s the coolest one, despite all the secondhand embarrassment you’ll feel for her. It’s true, she faces so many high school student nightmares all within a span of a few months, but in the end, I’d say things work out pretty magically for her. Of course, it’s a Cinderella story, so her life would play out like a fairytale, but at the same time, she was not always graceful. 

Aquamarine (2006) dir. by Elizabeth Allen Rosenbaum

Who could ever hate Aqua (Sara Paxton)? She taught her human friends so much about friendship, love and changed their perspective on multiple relationships they had with the different people in their lives. She wasn’t the perfect person and had a lot of learning to do herself, but the girls she made friends with taught her about unconditional love. Rewatching this movie is great when you want to see coming-of-age mermaid content but don’t feel like going through the entirety of the H2O: Just Add Water series. The soundtrack is full of bangers, too!

She’s the Man (2006) dir. by Andy Fickman

This movie is just effortlessly funny. Most of the humor comes from the facial expressions Amanda Bynes makes alone. This is yet another modern adaptation of Shakespeare, this time inspired by Twelfth Night. It’s full of twins trading places, gender-swapping, Shakespeare allusions, inaccurate soccer moves, and much more! 

John Tucker Must Die (2006) dir. by Betty Thomas

Scheming, love triangles, and high school cliques, this movie has all the cliches without being typical at all. If you’ve watched The Other Woman (2014), this is the original. Some of the mischief is the same in both movies, but this one takes place between teenagers and is not as disgusting at some points. I will say both movies are good and I have watched both uncountable numbers of times, but this one did it first!

Angus, Thongs and Perfect Snogging (2008) dir. by Gurinder Chadha

Based on the book series Angus, Thongs and Full-Frontal Snogging by Louise Rennison, this movie is full of chaos. Being a freshman in high school was much more mellow than what is displayed in the movie, but the mortifying puberty-related moments were far too relatable. For some reason, watching Georgia’s (Georgia Groome) cringe beauty flops or fails with her crush Robbie (Aaron Johnson, before he was Taylor-Johnson) brings feelings of comfort and bliss that I am not willing to give up any time soon.

Wild Child (2008) dir. by Nick Moore

In my opinion, this might be one of Emma Roberts’s best roles. Poppy is a powerful character. She has many faults in the beginning and learns to grow once the people at her new school quickly humble her. The personalities of every character and the reckless schemes they do complete this movie and Emma Roberts is just too good at playing a rude, pretentious rich person. It’s even more satisfying to watch the arch-nemesis get what she deserves, too.

The Clique (2008) dir. by Michael Lembeck

This movie is based on Lisi Harrison’s book series under the same name. There were SO many books that I’m absolutely heartbroken only one movie exists and it’s based on only the first book. We really won’t get to have any of the other books come to life. There’s quite a lot of bullying involved, but every character is mean in some way and deserving of what they get. Not a single person out of the main characters had good intentions with their actions until late in the movie, but that’s what makes it so fun.

To All the Boys I’ve Loved Before (2018) dir. by Susan Johnson

This is the only movie in this lineup that has a non-white main character which is even more reason for the comfort I feel from it. I haven’t yet finished the original book series by Jenny Han, but I’ve heard that the movie series hardly follows the plot at all. Looking at the movie separately from the books, I think TATBILB is a wholesome, pure coming-of-age, teen romance that has an interesting meet-cute and a concept that hasn’t really been done before. 


If you enjoy these movies, you can check out my Letterboxd list of films that I think bring the same feelings of comfort here. All the movies have common features that make them so enjoyable. While the others on the list are movies that I haven’t been able to watch at least five times (I’m assuming) like the ones mentioned above, they are definitely on the same level of fun and bring all viewers happiness.

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