Posted by Jenika Enoch @DrFink
I love movies, music, and art. I finished school for graphic design and love to be creative as much as humanly possible. ⨺
Jenika Enoch

We have reflected on the great teen movies of the 90s, but the following decade contained some great teen movies as well. The #2000s brought us even more romantic comedies, horror romps, and comedies that left us in stitches for weeks at a time.

With this article, we will take a trip down memory lane and talk about the best teen movies of the 2000s. Instead of the year 1999 delivering a majority of films on the list, the majority in this case comes from the year 2004. Must have been a lucky year! Also similar to the #90s list, these are not in any particular order.

While I'm not saying any of these are better than others, they are all favorites of my generation and each have something unique to love about them. Also bear in mind that this list will only contain movies from the first decade of the 2000s, so don't panic if you don't see something that has been released in 2010 and beyond. That's another list for another time. Here are our best teen movies from the 2000s!

Disclaimer: This list is updated with new movies from the 2000s each month. Also, it is in no particular order!

Donnie Darko (2001)

While most might not classify this sci-fi-thriller as a "teen movie," it does deal with the struggles of coming of age quite a bit - among many other things. Donnie Darko follows a troubled teenager as he begins having visions of a man-like bunny rabbit telling him to commit acts of crime after escaping a freak accident. Sounds pretty out there, right? Well, it is definitely not a concept you see every day.

Donnie Darko covers a wide spectrum of subjects including relationships, sex, mental illness, teenage delinquency, child abuse, and time travel. It is honestly one of those movies you just have to see to really believe (or understand), but it didn't reach the status of a cult classic for nothing. This is a well respected film and it definitely makes you question a lot of things that you might not have thought about before. Not to mention it has an amazing cast consisting of Jake Gyllenhaal, Jena Malone, Drew Barrymore, and the late Patrick Swayze.

Loser (2000)

Smack dab in the middle of Jason Biggs' American Pie fame, we had this early 2000s offering featuring him as Paul, a young college student who moves to New York City after receiving a full scholarship to college. Upon arriving in the Big Apple, he finds that his small town upbringing makes him the biggest fish out of water - that is until he develops a crush on a mysterious classmate named Dora who is more interested in their professor than him.

Loser is a rather underrated movie, in my opinion. Not only is it incredibly funny, but it touches on a lot of subjects that we all face as we branch away from the security of high school into the university environment. All of a sudden you're forced in with people with different backgrounds, different interests, and different lifestyles. As Paul encounters things that he never experienced before, such as underage drinking and drug use, he finds a way to stay true to the person he really is and learns that in order to make friends (or land the girl), you just have to continue to be yourself - even if your usual self is being a total nerd.

Josie and the Pussycats (2001)

"I'm here because I was in the comic book."

Josie and the Pussycats was basically a comic book adaptation before they were popular, and it is just as hilarious now as it was then. The story follows the girl-band trio, The Pussycats, as they achieve sudden mainstream success after signing with a major record label. The question is whether the group will stay together, or even stay alive in the process.

This movie starred a lot of actors that have gone on to achieve greater success in film and television, such as Rosario Dawson, Alan Cumming, Parker Posey, Missi Pyle, Tara Reid, and Gabriel Mann. Aside from a great cast, the plot in itself is actually very funny. The whole story is basically a satire of American consumerism with popular brands being pushed everywhere you turn. If it's not Starbucks, it's Gatorade. If it's not Gatorade, it's McDonald's or Coca-Cola. If you've never seen it, you're definitely missing out on some real fun. Not to mention the music is quite well done, too.

The Virgin Suicides (2000)

Similar to the 90s staple, Cruel Intentions, The Virgin Suicides was one of those movies that you didn't want your parents to know you'd seen. Its heavy thematic overtones and questionable subject matter definitely wasn't an easy sell to a lot of people. The story follows five sheltered sisters as they become a target of obsession from local neighbor boys in the 1970s.

In addition to starring popular actors of the decade, such as Kirsten Dunst, Josh Hartnett A.J. Cook, and Robert Schwartzman, the film touched on controversial subjects such as suicide, sexuality, religion, repression, and love. It's oddly one of those movies that you just have to see to really understand. Being that it was released in early 2000, The Virgin Suicides definitely set an interesting pace for what was yet to come within this decade.

Bring It On (2000)

"This is not a democracy, it's a cheerocracy."

Bring It On brought in the 2000s with a bang and most of it had to do with the witty dialogue. This movie tells the story of Torrance after she's named the new cheerleading captain for Rancho Carne High School. The promotion introduces her to a brand new world of teen politics and leadership after she finds out her predecessor stole the squad's cheers from the East Compton Clovers.

The movie introduced us to spirit fingers, the world of choreographed competitive cheerleading, and to a grown up Jesse Bradford. It was a good time to be a teenager. Despite the lame sequels and the reputation of being a "girl movie," I always defend Bring It On because it is actually very funny.

The Princess Diaries (2001)

Responsible for launching Anne Hathaway into stardom, this Disney tale of an unpopular, awkward teenage girl named Mia who finds out she's a princess was a pretty big hit with audiences. Starring Julie Andrews alongside Hathaway, The Princess Diaries was a fun way of introducing the idea that although you might not be all you want to be, or think you can be, but that being yourself is the best thing in the end. It also gave us a look into how a lot of us can underestimate our potential. Not to mention the fact that Mandy Moore plays a great mean girl.

I've always liked The Princess Diaries and I personally found Mia to be a very relatable character. It's funny and it does have a pretty good message attached to it when all is said and done. Even if you doubt yourself or don't believe that you could ever be destined for greatness, that doesn't mean that you're incapable of achieving something great. Just have confidence in yourself and you can do the unthinkable and influence change for the better.

Orange County (2002)

"I hate my job, I'm gonna burn this mother down!"

Orange County is one of the more hidden gems of the 2000s. The film has a great cast and is absolutely hilarious. It stars Colin Hanks as Shaun, a former surfer with a dream of getting accepted into Stanford University so he can get out of Orange County and become a writer. After being rejected by mistake, Shaun goes through unimaginable hoops to try and prove how badly he belongs at Stanford.

The humor wasn't the only thing that made Orange County a great movie. It was one that focused on the stress of choosing a path after high school and the anxiety that comes with your most desired plans not working out. We've all been there when it came to applying for colleges or even applying for jobs. Sometimes rejection is your answer despite how confusing it can be.

Swimfan (2002)

Swimfan was the movie that terrified your guy friends into never cheating on their girlfriends... at least for a little while. A loose adaptation of Fatal Attraction, it follows a high school swimmer (Jesse Bradford) as he encounters a new transfer student (Erika Christensen) and soon cheats on his girlfriend with her. He quickly becomes a target as their relationship spirals out of control and she becomes violently obsessed with him.

I can still watch Swimfan to this day and have fun watching it. The premise is a mixture of believable and ridiculous, but the crazy that Erika Christensen was able to channel for the character of Madison Bell was spot-on and it's just plain fun to watch her go nuts. Not quite as good as Glenn Close in Fatal Attraction, but it's pretty close.

13 Going on 30 (2004)

This was a bit different take on the whole body swapping concept and I always thought it worked out fairly well. After wishing on her 13th birthday to be grown up, Jenna (Jennifer Garner) wakes up the next morning as her 30-year old self only to find that her life hasn't quite turned out the way she wanted it to as a teenager.

I'll admit that 13 Going on 30 is one of the more cute teen movies of the decade, but I still enjoy watching it from time to time. The morality of it and the way that Jenna manages to adapt and change the course of her destiny was a good message for the children.

Sugar & Spice (2001)

This was the other cheerleading movie of the decade and what set it apart was the completely different concept. Unlike Bring It On, this movie focused on a group of high school cheerleaders as they devise a criminal plan to support the lifestyles they want to have after graduation. The film starred Marley Shelton, Mena Suvari, Melissa George, Rachel Blanchard, and James Marsden.

I always thought Sugar & Spice was funny and it was one of the few movies of the 2000s that more resembled a movie of the 90's. The plot was different enough and it did contain a lot of humor and situations that were definitely more mature.

Step Up (2006)

Yeah, we all know the sequels are nothing to go crazy about but the original Step Up wasn't all that bad. It wasn't until Magic Mike where we were reminded of what a great dancer Channing Tatum is, but it all started with this film where he plays an underprivileged street dancer that is sentenced to serve community service hours at a Maryland school for the arts. His talents are quickly discovered and he is given the opportunity of a lifetime.

The story itself isn't completely unbelievable and it lends a hand to the struggle with a lot of inner-city teenagers that have the talent but not the means. I wouldn't really recommend the sequels, but if you've never seen Step Up I would give it a shot.

Sisterhood of the Traveling Pants (2005)

Despite the long and rather obnoxious title, The Sisterhood of the Traveling Pants was a pretty decent movie for its time. The film follows four friends as their lives all start to go in different directions while spending a summer apart. To keep their friendship together, they pass along a pair of jeans that magically fits each of them perfectly.

For what it's worth, the cast of Alexis Bledel, Blake Lively, America Ferrera, and Amber Tamblyn wasn't that bad and it was fairly believable that these four girls were best friends. The movie deals with relationships, friendship, and family in a fairly heartfelt way.

The Girl Next Door (2004)

One of the more raunchy films on the list, this R-rated romp told the story of what can happen when a girl out totally of your league moves in next door. Emile Hirsch stars as a high school senior named Matthew who's dreams come true after a porn star (Elisha Cuthbert) moves into the house next door and shows interest in him.

I like this one primarily because it's a funny movie and for the decade it did fit in. Right at the beginning of the digital age, it shows how high school and teenagers began to change with the introduction of technology into our every day lives. It also showed the flip side of the adult industry and showed that porn stars aren't just plastic drones being filmed all the time. They are real women that want relationships with good guys. Isn't that what all of us girls want?

Save the Last Dance (2001)

I remember really liking this movie when it came out. Starring Julia Stiles and Sean Patrick Thomas, it follows a privileged girl named Sara (Stiles) as she is forced to move to a predominantly black neighborhood in Chicago. Shortly after befriending Chenille (Kerry Washington), she begins an interracial relationship with her brother Derek (Thomas) and has to come to terms with his criminal past.

A lot has happened regarding race relations in the US since 2001, but I think this movie is worth reflecting on because although not completely intentional, it does show a lot of racial struggles that do exist. I grew up not too far away from a school in a pretty bad neighborhood and I remember kids who would transfer to my school and say it was nice to be able to set their backpacks on the ground without having someone steal something. I thought this film reflected on the time and culture quite well.

Napoleon Dynamite (2004)

Admit it, we all quoted Napoleon for a solid year after this came out. The fun thing about Napoleon Dynamite is it was a movie unlike something we had seen. It was quirky, funny, awkward, and oddly clean cut. Written and directed by newcomer Jared Hess, it told the story of an alienated teen in a small Idaho town who decides to help his new best friend run for class president.

The funny thing about this movie was the fact that Napoleon was essentially all of us on the inside. He just wasn't afraid to show it. He had an awkward family life, he was easily annoyed and rather quick to anger, and he just wanted to be himself regardless of what anyone thought. Without this movie I wouldn't have had my entire sophomore biology class yell, "Tina you fat lard!" in perfect unison.

Crazy/Beautiful (2001)

Probably one of the more forgotten movies of the decade, Crazy/Beautiful was another instance of a couple from two completely different backgrounds struggling to make it. As they encounter each other at school, Carlos (Jay Hernandez) quickly falls for Nicole (Kirsten Dunst). He begins to unravel that despite her wealthy and privileged upbringing, she has a lot of problems and pain that runs deep. Carlos struggles to keep up as Nicole's reckless behavior puts his scholastic career at risk. Under pressure from himself, his family, and Nicole's family, he is forced to make a choice between his future and his relationship.

I liked this movie for what it was and I thought it held a rather interesting message about relationships and love. You don't really get to choose who you fall in love with and it just sort of happens. Sometimes it happens with the least expected person. It all comes down to what's more important to you and what you're willing to fight for.

Freaky Friday (2003)

Although this is yet another take on the body swap concept, the way this adaptation of Freaky Friday did it was a bit different and it brought it up with the times in a pretty decent way. The characters were fun and you can't deny that Jamie Lee Curtis played a teenage mind pretty well.

Curtis starred alongside a pre-disaster Lindsay Lohan as the mother/daughter pair of Tess and Anna. After an explosive argument, they are gifted two fortune cookies which swaps their personalities until they can prove to each other that they have the ability to be selfless for the sake of the other person's happiness. The way they updated this version was making the mother a very rigid career mom type and the teenager a complete troublemaker complete with attitude ridden friends and a garage band.

Although being more aimed at younger teens, the film did touch on rather deep subjects such as parental death, remarriage, bullying, and relationships. I thought the way those themes were handled and resolved was done quite well and it left you with a feel-good ending.

Charlie Bartlett (2007)

Charlie essentially is a rich kid who has been expelled from every private school he's ever been to. Upon his entrance to public school, he is quickly bullied and his quest for popularity seems hopeless. That is until he starts a business plan and becomes a self-appointed psychiatrist for the student body in exchange for prescription drugs.

Charlie Bartlett was one of those movies you thought you remembered hearing about, but you probably never took the initiative to actually see it. I will admit it's been a number of years since I have seen it, but I do remember liking it for what it was. Charlie was that kind of person everyone dreamed they could be deep down. Definitely back in the days where the late Anton Yelchin was just plain adorable. It also helped Kat Dennings' star power a little bit.

Superbad (2007)

Michael Cera and Jonah Hill starred as Seth and Evan, two high school virgins who have been best friends since elementary school. Jealousy and insecurity come into play after they are accepted into different colleges and are getting nowhere with their crushes. The events leading up to graduation, and a booze-soaked party, test the limits and strength of their friendship.

It took me a couple of viewings to actually appreciate Superbad for what it was. However, I thought for what it's worth it was funny enough and it does carry a decent message of what it takes to face growing up after graduation and how to carry your friendships through the change. Plus, without this movie we wouldn't still be making McLovin jokes and remembering the time Emma Stone's bangs covered half of her face.

Juno (2007)

This is a great film with a lot of heavy thematic elements, the biggest and most obvious being teen pregnancy. Juno MacGuff was brought to life by Ellen Page in this story of a teenage girl who is accidentally impregnated by her friend Paulie (Michael Cera). After weighing her choices, she decides to give the baby up for adoption and finds Mark and Vanessa, a wealthy but struggling couple played by Jennifer Garner and Jason Bateman.

Juno is one of the most critically acclaimed movies on the list as it won Diablo Cody an Oscar for Best Original Screenplay and earned Ellen Page a nomination for Best Actress. What Juno did right is it played teenagers in a realistic light. Despite the sometimes overly witty and ridiculous dialogue, this girl and her counterparts aren't stupid and totally clueless which is how a lot of teenagers of the decade were portrayed. Juno realizes as a 16-year old she is inadequately fit to be a mother and she acts on what she believes is right, even if that means breaking her own heart in the process.

Nick and Norah's Infinite Playlist (2008)

Fresh off a break up, Nick (Michael Cera) is dragged to NYC to perform a gig with his band mates. Little does he know, his ex-girlfriend shows up to crash the show with her new boyfriend and friends including a shy, under confident girl named Norah (Kat Dennings). Nick and Norah come together by complete chance but the pair quickly find out that although they had heard about one another through the perspectives of their friends, they had a lot more in common than they could have ever thought.

I thought the characters were what brought this movie to life and also the subtle way they showcased the city of New York as a supporting character on its own. The random events that happen throughout the movie wouldn't have been so important without the city setting. Nick and Norah are those kinds of teens we all knew back in the day and the way they are brought to life and explained is something not everyone got to see while in school. Sometimes all the misunderstood want is a chance to explain themselves to someone willing to listen. Plus, the soundtrack is pretty awesome.

A Walk to Remember (2002)

A Walk to Remember was not only the movie to fully launch Mandy Moore into stardom, but it was one of the main movies of the decade to make everyone cry their eyes out. The film follows a troubled teen named Landon (Shane West) who is forced into community service after a prank gone wrong. While serving his time, he encounters an unpopular girl named Jamie (Moore) and quickly finds himself unable to resist her as she holds a life and view on the world that he wishes he had.

Keep in mind that this is a Nicholas Sparks story. However, this is one of the best film adaptations of his novels. The casting was practically perfect and the story itself was a mixture of happiness and heartbreak in a way that didn't make you mad at any of the characters, but more happy that they were able to have the experience at all.

Adventureland (2009)

Adventureland is another one of those movies you probably heard about but never watched. Either that or you caught a little bit of it on television but didn't pay much attention. It's a shame because it's actually a really great movie.

After James (Jesse Eisenberg) graduates from an ivy-league journalism program, he is forced to forfeit a planned summer trip to Europe and take a summer job at an amusement park. While thrown into a world he's never really experienced, he encounters a mysterious girl named Emily (Kristen Stewart) and quickly pursues her only to discover a secret she's been hiding from the entire staff.

Although it takes place in the late 1980's, Adventureland is funny, sweet, and very meaningful at times. The characters are written extremely well and the entire subculture of yuppie vs. lower-class is thrown into a giant melting pot inside the park. What you wouldn't expect to work does and it leaves you with a smile on your face. It also extends further proof that outside of the Twilight franchise, Kristen Stewart is a pretty good actress. If you've never taken the time to actually watch it I would recommend giving it a try.

Speak (2004)

The one and only television movie to make the list, Speak was a movie you no doubt saw at some point in middle or high school but probably couldn't remember seeing it. Starring Kristen Stewart, it told the story of a high school freshman named Melinda Sordino who makes an elective vow of silence after a blurry traumatic experience over the summer changes her perspective on life.

This was the movie that essentially put Kristen Stewart on radar and to this day it remains one of her best performances. The way she was able to channel the character of Melinda was pretty fantastic and the movie itself was pretty close to the book by Laurie Halse Anderson. The events of the film are unraveled in a way that keep you interested and make you want to know what happened to Melinda. It also puts entering high school into perspective and shows the consequences of how friendships end, but it also shows how people can come back together in the revelation of something horrible.

Mean Girls (2004)

"Stop trying to make fetch happen! It's not going to happen!"

You can't talk about teen movies without mentioning Mean Girls. It's no doubt one of the best the decade produced and definitely one of the most influential on the generation. As Cady (Lindsay Lohan) enters North Shore High School after living in Africa her whole life, she is accepted into the A-group clique known as The Plastics and quickly runs into trouble when she begins crushing on the queen bee's ex-boyfriend.

I remember seeing Mean Girls when I was a freshman in high school and it was as relevant then as it is now. The cliques were real, the characters were believable, and the truth is we all knew someone like Regina George. She existed in all of our schools along with her minions. The witty dialogue and girl-code insults were genius and they maintain to this day. I still find myself quoting Mean Girls with my friends whether it's one line or entire conversations. It not only gave us somewhat of a code for communicating with each other, it gave us genius ways of getting around what we all wanted to say but knew better than to actually say it.

Saved! (2004)

This is easily another 2000s movie that I don't think a lot of people have seen. Saved! was a satire on a lot of popular subjects including teen pregnancy, relationships, homosexuality, and religion. The basic plot follows Mary (Jena Malone), a senior at a private Christian school who becomes pregnant and is quickly rejected by her old friends after she begins to question her faith in God.

The plot sounds simple and maybe somewhat corny, but it has a lot deeper themes running through it and as a religious person I always found it to be funny and meaningful at the same time. It showcases how a lot of "hardcore" religious groups are perceived by the media and the public and kind of puts it on parade, specifically with Mandy Moore's character Hilary Faye. It also puts into perspective what a lot of people believe can cure homosexuality. However, it shines a light on whether the programs are really helpful or if it's a way to just hide whatever is deemed unacceptable and make the families feel better, not the individuals sent there.

What I really love aside from the thematic elements is the characters and the cast. The cast, alongside Jena Malone and Mandy Moore, is made up of Macaulay Culkin, Eva Amurri, Patrick Fugit, Heather Matarazzo, Mary-Louise Parker, and Martin Donovan. The characters they play are a mixture of the devoted, the rebellious, and the in-between. In other words, the mixture you find in every day life and we all have something to learn from one another. You might not think so, but we do. It's all about who we should be, who we can be, and who we want to be.

Thirteen (2003)

Thirteen follows Tracy (Evan Rachel Wood), a somewhat nerdy 7th grader who is best friends with her mother, Melanie (Holly Hunter). Tracy's relationship with her mother and old friends is put to the test when she befriends Evie, a troubled and overly mature girl at school. Very quickly we see Tracy introduced to a wide open world of sex, drugs, and crime as her personal life begins to spiral into abuse, self-harm, and isolation. The scary part is how quickly Tracy spirals out of control and the lengths she goes to try and hide it. The pain felt from divorce, separation, and trying to appear like a perfect teen angel for her family only drives her to rebel even more and go to every possible outlet to numb the consequences.

Aside from the fantastic performance from Evan Rachel Wood, there is an equally great delivery from Holly Hunter. The way she adapts to the change in Wood's character shows that the struggle isn't always with the child. I've been told by my parents that watching your children go through things is one of the hardest parts of raising children because there really isn't anything they can do but watch.

Thirteen resonated very strongly with me as a teenager and I related a lot to the characters and the situations. It was realistic in the sense of exactly how quickly things can fall apart and also the changes that are both exciting and scary. It just depends on which side of the fence you're on. If you've never seen this movie I would recommend watching it because even if you didn't experience it, you know people who did.

What was your favorite teen movie of the 2000s? Let me know in the comments!