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VOICE OVER: Emily - WatchMojo WRITTEN BY: Savannah Sher
Now that we're two decades in, it's time to start evaluating our favorite teen movies of the century so far. For this list, we'll be looking at our favorite films that center on teenagers and/or adolescence that were released in 2000 or later. Our countdown includes “She's the Man,” “Booksmart,” “Lady Bird,” and more!
Now that we’re two decades into the century, it’s time to start evaluating our favorite films. Welcome to MsMojo, and today we’ll be counting down our picks for the Top 20 Teen Movies of the Century (So Far). For this list, we’ll be looking at our favorite films that center on teenagers and/or adolescence that were released in 2000 or later.

#20: “Me and Earl and the Dying Girl” (2015)

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While some of the movies on our list today are going to be lighthearted high school romps, this isn’t one of them. Despite the fact that it deals with a teen facing terminal cancer, “Me and Earl and the Dying Girl” actually has much more levity than you would imagine. It’s a sweet coming of age film that looks at the typical experience of being a teenager, with the added gravity of being confronted with mortality. It’ll make you laugh, it’ll make you cry, and you’ll certainly be thinking about it long after it’s over.

#19: “She's the Man” (2006)

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Who knew that William Shakespeare's comedic play “Twelfth Night” would make the perfect background for a hilarious teen romance movie? In this 2006 film, Amanda Bynes plays Viola Hastings, a girl who loves playing soccer, but is dismayed when her team is cut. She decides to take matters into her own hands and disguise herself as her twin brother Sebastian and play for the guys’ team instead to prove a point. This movie is, of course, full of laugh out loud hijinks, especially when Viola finds herself falling for one of her teammates.

#18: “A Cinderella Story” (2004)

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Some of the movies on our list are critically acclaimed films that received Oscar nominations, but this one didn’t exactly fare well with the critics, receiving a dismal 12% on Rotten Tomatoes. But critics aren’t the only ones with opinions, and we love this charming modern day fairy tale starring Hilary Duff and Chad Michael Murray. Does it make sense that Austin doesn’t recognize Sam just because she’s wearing a small mask? No. But do we care? Definitely not. Of course this movie has a picture perfect happily ever after, and we wouldn’t have it any other way.

#17: “Sing Street” (2016)

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This low budget production was a collaboration between Ireland, the US and the UK, and the result was a perfect teen movie about a Dublin adolescent in the ‘80s who starts a band with the goal of getting his crush to fall for him. The movie even received a nomination for Best Motion Picture – Musical or Comedy at the Golden Globe Awards. If you’re a music fan looking for something uplifting that’ll leave you wanting to sing along with the characters, look no further than this sadly underrated movie.

#16: “Eighth Grade” (2018)

We never could have imagined that comedian Bo Burnham could have created such a heartfelt film about a young teenage girl living in the social media era, but in 2018, he did just that, impressing critics and viewers in the process. Elsie Fisher shines as the desperately awkward protagonist Kayla, who you can’t help root for throughout the story even if you’re busy cringing and covering your eyes while remembering your own uncomfortable middle school experiences. This movie will break your heart and leave you wishing you could see Kayla living her best life all grown up.

#15: “Freaky Friday” (2003)

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Before Lindsay Lohan became known for her antics in the tabloids, she was starring in adorable teen comedies like “Freaky Friday”. The premise is that she’s a rebellious teen who doesn’t see eye to eye with her mother about anything, until they inadvertently switch bodies one day. Both Lohan and Jamie Lee Curtis do a remarkably good job of impersonating each other’s mannerisms and the film comes to a surprisingly emotional conclusion. Not to mention, this movie made little rocker chicks out of many of us when we saw it in high school!

#14: “Juno” (2007)

Has there ever been such a hilarious look at unintentional teen pregnancy? When it was released in 2007, “Juno” was a massive critical and commercial success, making $231 million on a budget of under $10 million. It looks at a the story of a 16 year old girl who decides to give her baby up for adoption after becoming pregnant by mistake, and while the movie starts off as quirky and full of comedic relief, it takes a more serious and unexpected turn as the action progresses, leading to a conclusion that is both surprising and poignant.

#13: “Bring It On” (2000)

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2000’s “Bring It On” opens with a bang, as we see Torrance Shipman have a cheerleading nightmare dream sequence. What follows is a movie that keeps up an exciting pace, shows us fun cheer routines, a bit of romance and even tackles racism and class disparity. While some movies from this era don’t hold up well 20 years later, this one is just as likable as it was upon its release. While it may not have been initially critically acclaimed, it has achieved cult classic status in the years since.

#12: “Booksmart” (2019)

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The elevator pitch for this movie, which was directed by Olivia Wilde, could have been “Superbad, but with girls”. But the end result was so much more. Beanie Feldstein and Kaitlyn Dever star as two high school seniors who have spent their last few years focusing on academics rather than having a good time. They set out to have one epic night out before graduation and end up getting much more than they bargained for. It’s laugh out loud funny and manages to be silly while also being pretty woke.

#11: “Love, Simon” (2018)

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“Love, Simon” was notably the first time that a major Hollywood studio made a teen movie focusing on a gay protagonist, but beyond its historical significance, it’s also a deeply enjoyable film. While many LGBTQ narratives told in the mainstream look at the perils of being gay, this one takes a somewhat lighter, though still realistic look at what a teenager’s experience might be like coming out today. It features a sweet romance and a cast of likable characters that makes us think this will soon become a modern classic.

#10: “The Sisterhood of the Traveling Pants” (2005)

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It’s always tough to adapt a book that has such a loyal following, but they nailed it with the 2005 movie version of “The Sisterhood Of The Traveling Pants”. The story is about four friends who are very different from one another but who happen to fit into the same pair of second hand jeans, so they use the pants to keep them together even when they’re apart. The all star cast is what carries this movie, with Amber Tamblyn, America Ferrera, Blake Lively and Alexis Bledel each bringing plenty of heart to their sections of the story.

#9: “The Princess Diaries” (2001)

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Doesn’t everyone dream of suddenly finding out they’re in fact the princess of a small little-known country? We sure did! The modern fairy tale told in “The Princess Diaries” is tons of fun, as we watch Anne Hathaway play the hapless Mia Thermopolis, a clumsy and decidedly un-graceful teen living in San Francisco. When she finds out from her grandmother, played flawlessly by Julie Andrews, that she is actually the heir to the kingdom of a fictional country called Genovia, she has to quickly learn how to walk and talk like royalty. We’ll rewatch this move if just for that epic makeover.

#8: “A Walk to Remember” (2002)

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If you were a teen in the early aughts, you almost certainly had your heart broken by this Nicholas Sparks adaptation. “A Walk to Remember” introduces us to Jamie, a minister’s daughter who seems too pure for this world and Landon, a bad boy who’s part of the wrong crowd. When they’re thrown together, Jamie makes Landon promise that he won’t fall in love with her, which he takes as some kind of joke. But they do fall in love, only for their happy ending to be foiled by the fact that Jamie has been hiding her terminal illness from him. You’ll need the Kleenex for this one!

#7: “Easy A” (2010)

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Inspired by the events of Nathaniel Hawthorne’s “The Scarlet Letter”, “Easy A” stars Emma Stone as a high schooler who lies about losing her virginity to get her friend off her back. The casual fib spirals out of control and she finds herself helping her peers come up with equally untrue stories about their own sexual histories. Considering it came out a decade ago, the film does a remarkably good job of tackling the issue of slut shaming that wasn’t nearly as prevalent in the cultural dialogue at the time.

#6: “The Fault in Our Stars” (2014)

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If you think a story about two teenagers battling cancer who fall in love is going to be depressing...well, you’d be right. There’s no sugarcoating it: “The Fault in Our Stars” is certainly not a fun filled romp, but it is a movie that’s incredibly touching and shows the inner lives of two kids who are so much more than the diseases they are suffering from. The story takes you to unexpected places, and trust us when we say that the ending is not the one you were expecting.

#5: “The Perks of Being a Wallflower” (2012)

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It may have taken over a decade for Stephen Chbosky’s novel, “The Perks of Being a Wallflower”, to make it to the big screen, but when it finally did, fans were rewarded with an emotionally evocative film that did justice to its source material. That should come as no surprise considering the fact that Chbosky actually penned the screenplay and directed the film himself. This story about a high schooler dealing with depression and repressed trauma while just trying to make it through each day is both tragic and deeply relatable to anyone who has suffered from mental illness.

#4: “To All the Boys I've Loved Before” (2018)

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When Netflix released its teen rom-com “To All the Boys I've Loved Before” in 2018, people may not have had high expectations. But anyone who has watched it can tell you that this movie will make a fan out of pretty much any viewer. While it harkens back to teen flicks from the ‘80s in many ways, it also simultaneously feels strikingly modern with its diverse cast and subtly progressive values. Also any teen movie that can give us a couple we want to ship as much as Lara Jean and Peter is a good one in our books.

#3: “Lady Bird” (2017)

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While many of the movies on this list may have been popular with audiences, there may not be one quite as critically acclaimed as “Lady Bird”. With an impressive 99% on Rotten Tomatoes and five Oscar nods including Best Picture and Best Actress for Saoirse Ronan’s heartbreaking lead performance, Greta Gerwig’s solo directorial debut is a coming of age story that is not to be missed. Telling the story of a Sacramento teenager who has big dreams for herself, this film is at once hilarious and heartrending. The picture it paints of a mother daughter relationship would make anyone want to call their mom and tell them they love her.

#2: “The Edge of Seventeen” (2016)

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You might be surprised to see a movie so high on this list that many people have not seen, considering it only brought in $18 million at the box office. But considering this a ringing endorsement to watch “The Edge of Seventeen” if you haven’t already. It stars Hailee Steinfeld as Nadine, a girl who has to face her best friend starting to date her older brother while she’s still getting over her father’s death. The movie is very much set in the modern day, with a cringeworthy texting scene as one of its most memorable moments. Before we unveil our top pick, here are a few honorable mentions. “Dope” (2015) “Pitch Perfect” (2012) “Pariah” (2011) “Superbad” (2007)

#1: “Mean Girls” (2004)

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There is no movie that has defined the teen genre more this century so far than this one has. “Mean Girls” tackled the high school comedy in a snarky and satirical way that makes it stand out among the pack. Regina George and her band of Plastics are an over the top version of the mean girls that exist in nearly every high school, and the way this film portrays cliques feels oh so real to many. Its legacy and cult following don’t look like they’re going anywhere anytime soon, with so many quotes and concepts from the movie having entered the cultural lexicon. You go, Glen Coco!

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