To keep this resource free, is compensated by certain providers listed below. Learn More To keep this resource free, is compensated by certain providers listed below. Learn More
A teen girl and boy go in for a kiss in this image from Summit Entertainment.
Love it or hate it, “Twilight” was an iconic film from the 2000s, one you might look at differently today. (Image: Summit Entertainment)

Before social media, we lived in a simpler time. We hit up the mall with our friends, hopped on AIM to gossip, and spent our Fridays eating pizza and watching Blockbuster movies. Of course, it wasn’t all fun and games. If we’re being honest, not much of it was, given the surge in teenage depression and mental health issues, the dark cloud of the Iraq War, a growing generational divide that made us clash with our parents, and the pressure to navigate a constantly shifting information landscape. Yet, knowing it wasn’t all that great at the time shouldn’t stop us from looking back on the period with rose-colored glasses.

Movie lovers like myself often return to teen films of the 2000s, where everyone was skinny while eating daily takeout, lived in an L.A. mansion on a teacher’s salary, and wanted to be cool enough to be accepted by the popular crowd. Why? Because the nostalgic familiarity of those films brings us comfort. But when I rewatch some of my favorites with a more critical eye, I see things I didn’t quite grasp in my younger years and walk away with a new perspective. In fact, I think there are more than a dozen teen movies you should watch again through an adult lens.

‘Bring It On’ (2000)

Two cheerleaders face off in this image from Beacon Pictures.
“Bring It On” taught us about teamwork and originality. (Image: Beacon Pictures)

When watching “Bring It On” as a teen, not all of the political messages in the film hit home. It’s a fun, cheerleading-focused rom-com, and the fact that the main plot involves a white team winning using a Black team’s stolen routines felt more like storyline seasoning rather than the point of the whole film. But watching the movie as an adult, it’s clear that before cultural appropriation was widely discussed, “Bring It On” tackled the issue head-on.

Much of the film revolves around Torrance’s (Kirsten Dunst) team reinventing themselves before a national cheerleading competition after discovering their routines were taken from a rival team of color. The story of Torrance and her opposing captain, Isis (Gabrielle Union), as they go from tense adversaries to mutual admirers, isn’t a common interracial female relationship depicted in teen flicks. These elements set “Bring It On” apart from its contemporaries, depicting a profound experience many of us have as teenagers: realizing that wider societal issues affect us and that we need to respond to those situations with integrity.

“Bring It On” is available on Amazon Prime Video.

‘Freaky Friday’ (2003)

A daughter looks at her shocked mother in this image from Walt Disney Pictures.
“Freaky Friday” is a surprisingly touching look at mother-daughter relationships. (Image: Walt Disney Pictures)

“Freaky Friday” is a Disney movie about a punky girl switching bodies with her judgmental mother. As a teen, the on-point comedy, rockin’ music, and trendy style made this a very cool film. As an adult, I found myself crying at the heartbreaking climactic moments of Tess (Jamie Lee Curtis) and Anna’s (Lindsay Lohan) mother-daughter relationship. If you had tension with your mother growing up, you’ll get it, especially now that you’re older.

It’s easy to envy this duo in “Freaky Friday,” whose magical body-switching gives them the opportunity for real, firsthand understanding of each other’s lives. Feeling like your parents will never understand or believe you colors the teenage experience and is a dynamic that often continues into adulthood. Although we can’t really let someone step into our shoes like Tess and Anna did, I realized as an adult that it’s not completely necessary. We don’t need to let our happiness depend on others’ understanding of us — even our parents’.

“Freaky Friday” is on Disney Plus.

‘What a Girl Wants’ (2003)

A father and daughter have breakfast in this image from Warner Bros.
“What a Girl Wants” shows us that even parents can’t get in the way of you finding yourself. (Image: Warner Bros.)

When rewatching “What a Girl Wants,” you can still enjoy many of the things that made you love it as a teen: a funky soundtrack, Amanda Bynes as Daphne, a creative script, and over-the-top British stereotypes. However, you may notice upon watching as an adult that this story of a bohemian New York love child running away to England to meet her father, Lord Henry Dashwood (Colin Firth), has a lot more substance than first meets the eye.

Daphne’s attempt to change herself to fit the pomp and circumstance of the British nobility may be a little exaggerated, but it’s an effective metaphor for the masking many of us find ourselves having to do throughout our lives — especially while growing up. Daphne ultimately decides it’s not worth changing for anyone, even her dad. In life, these kinds of realizations might not come as easily or quickly as they do in a 105-minute movie, but they reminded me that we do have to find a way to be true to ourselves and choose our identity without anyone’s influence, including that of our parents.

You can rent or buy “What a Girl Wants” on Amazon Prime Video.

‘Thirteen’ (2003)

Girls chat outside a high school in this image from Fox Searchlight Pictures.
The controversial drama “Thirteen” was shocking and sadly accurate. (Image: Fox Searchlight Pictures)

“Thirteen” isn’t an easy rewatch, as it very effectively captures the confusion, frustration, depression, and rage that came with being a teen in the early 2000s. Most of the films on this list are lighthearted comedies that couldn’t be more different from this R-rated, semi-autobiographical drama cowritten by the film’s emancipated 14-year-old star, Nikki Reed, and future “Twilight” director Catherine Hardwicke. It was highly controversial at the time for its depiction of age-inappropriate behavior from its shockingly young protagonists.

Middle-schooler Tracy’s (Evan Rachel Wood) complicated emotional life and descent into being a “bad girl” after befriending troubled orphan Evie (Reed) feels all too real at times. My mom watched this film when I was 11 and it scared the heck out of her, so I didn’t watch it myself until my older teens. But of all the movies I’ve included here, my perception of this film changed the least from youth to adulthood. It was raw then, although I only related to Tracy’s emotional state and not her character. It’s still raw now, as I look back with heartbreak on a whole generation who felt on-fire inside and know that it hasn’t changed much for today’s teens.

“Thirteen” is available to stream on Hulu.

‘Holes’ (2003)

Boys in jumpsuits sit in the grass in this image from Walt Disney Pictures.
“Holes” was a Western adventure with strong teen lessons. (Image: Walt Disney Pictures)

As an avid young reader, the young adult bestseller “Holes” by Louis Sachar was one of my favorite books. So when the film came out, I was mostly excited to see a beloved story brought to the big screen. Rewatching the film as an adult, it’s clear why I liked it. This Neo-Western about unlucky teen Stanley Yelnats (Shia LaBeouf) digging holes in the desert at a juvenile detention facility as penance for a crime he didn’t commit drives home heavy themes.

Facing injustice at the hands of authority, showing patient commitment to your friends, and finding your values in hardship are things most of us can relate to by adulthood, allowing the morals of the story to resonate more profoundly upon rewatching today. Also, as an adult who is now a big mystery fan, the core mystery surrounding the discovery of an old lipstick tube and buried bandit treasure is even more fun to see unfold now than it was when I was a kid.

“Holes” is available with a Disney Plus subscription.

‘Raise Your Voice’ (2004)

A boy plays guitar while a girl plays piano in this image from New Line Cinema.
Hilary Duff gives her best performance in “Raise Your Voice.” (Image: New Line Cinema)

It wouldn’t be a 2000s teen movies list without an appearance from our girl-next-door icon, Hilary Duff. As a “Lizzie McGuire” stan from day one, I never missed a film my girl Hilary made. Now that I’m a true film buff, I recognize she wasn’t an amazing actress compared to some of her peers, but that doesn’t make me love this wholesome queen any less. Duff’s best performance was in “Raise Your Voice,” where she played sheltered Arizona teen Terri Fletcher, who sneaks off to attend a prestigious music school in L.A. after surviving a car accident that killed her brother.

Terri is relatable and nuanced as a teen haunted by PTSD, and Duff gives impressive musical performances throughout the film. Her journey to overcoming her trauma has a lighter depiction than the heavy drama “Speak,” which starred Kristen Stewart and also came out that same year, but both have similar themes of rediscovering your voice. Watching as a teen, it was easy to relate to not being able to express yourself, but at that age, most adolescents don’t overcome that obstacle like Duff’s character does. This makes Terri’s story seem pretty grand. As adults, most of us have “found our voice” in some way, making her story seem less spectacular and more relatable.

You can rent or buy “Raise Your Voice” on Amazon Prime Video.

‘Chasing Liberty’ (2004)

A woman yells out in joy on the back of a man’s motorcycle in this image from Alcon Entertainment.
“Chasing Liberty” fulfills the “great escape” desire that’s common among teens. (Image: Alcon Entertainment)

As someone who flew off to Europe as soon as I turned 18 in search of wild parties and whirlwind romances, I relate to “Chasing Liberty” more than the average person. This film about First Daughter Anna Foster (Mandy Moore) ditching her Secret Service detail to go on a cross-continent adventure and attend the EDM festival Love Parade in Berlin, has a more mature protagonist than other works on this list, but still showcases very teenage themes.

The desire to escape our boring hometown for a life of adventure was pretty universal among the people I knew in high school. Having now done that, I wouldn’t change a thing, and I would encourage any teen today to jump at similarly rare and exciting opportunities when they come their way. Meanwhile, when watching “Chasing Liberty” again, Anna, whose desire to experience love, danger, freedom, and self-discovery is infectious, can reinspire us boring and jaded adults to embrace our youthful zest for life.

You can watch “Chasing Liberty” on Amazon Prime.

‘Mean Girls’ (2004)

Three students sit in the grass in this image from Paramount Pictures.
“Mean Girls” is arguably the most beloved teen classic from the 2000s. (Image: Paramount Pictures)

There is no 2000s teen movie list without “Mean Girls,” the most enduring classic of the era. It’s just as funny every time you watch it, with the memeable script continuing the film’s pop-culture legacy to this day. The flick also paved the way for the 2024 “Mean Girls,” an adaptation of the Broadway musical inspired by the original film.

Most teens, no matter how much they feel like it, aren’t actually “outsiders” in the way Cady Heron (Lindsay Lohan) was in the film. Her home-schooled upbringing in Africa is more effective at providing adults, the real outsiders to high school politics, a window into the bizarre social world of teenagers. The meat of the plot is directed at teens who may still be immature enough to fantasize about taking down school bullies, with the story ultimately warning you not to lose yourself for a vendetta. As an adult who would never make the same choices as Cady, it now reads to me as more of a psychological comedy-drama, exploring the extreme lengths someone may go to to impress others.

“Mean Girls” is available to rent or buy on Amazon Prime and stream on Paramount Plus.

‘The Sisterhood of the Traveling Pants’ (2005)

 Four girls link arms in an airport in this image from Alcon Entertainment.
“The Sisterhood of the Traveling Pants” captures four diverse young women’s experiences. (Image: Alcon Entertainment)

As a teen, the main draw of “The Sisterhood of the Traveling Pants” was the all-star cast of best friend protagonists: Alexis Bledel as Lena, Amber Tamblyn as Tibby, Blake Lively as Bridget, and America Ferrera as Carmen. As an adult, I’m more drawn to the movie as a beautifully shot montage of life lessons seen throughout one summer as four friends are scattered across the globe for the first time, connected by a pair of jeans that fit them all.

The film has nuanced themes that require accepting two opposing ideas: the importance of lifelong friendship and that some adventures can only be had alone. It’s a tale about female friendship in all their forms, and it’s been well-documented that adults struggle in that department. It may be time for a rewatch of “The Sisterhood of the Traveling Pants” to help you remember the importance of friendship and perhaps even inspire you to give an old pal a call.

You can rent or buy “The Sisterhood of the Traveling Pants” on Amazon Prime Video.

‘She’s the Man’ (2006)

A girl plays on a boys’ soccer team in this image from DreamWorks Pictures.
Shakespeare gets the Amanda Bynes treatment in “She’s the Man.” (Image: DreamWorks Pictures)

When I was a teen, “She’s the Man,” a modern retelling of Shakespeare’s “Twelfth Night,” got me in the door by heavily marketing all the gender-bending fun. It was good for my friends and me to get the gist of a major literary work, but mostly we wanted to see Bynes, a few years after “What a Girl Wants,” dressed up as a boy. In embarking on an adult exploration of the movie, I wondered how well or poorly it aged.

The film follows star athlete Viola Hastings (Bynes) as she poses as her twin brother in an attempt to make the boys’ soccer team after her girls’ team is cut. Between all the Shakespeare-level shenanigans, it can be hard to see some of the deeper messages in the movies as a teen. On my rewatch, though, it was clear that despite being a lighthearted romp, “She’s the Man” touches on important issues like gender equality, being taken seriously as a young woman, embracing femininity, being true to yourself, and being loved for who you are. In many ways, the movie was ahead of its time.

Watch “She’s the Man” with a Paramount Plus subscription.

‘Step Up’ (2006)

A girl and boy practice a dance routine in a ballet studio in this image from Touchstone Pictures.
We all fell in love with Channing Tatum in “Step Up.” (Image: Touchstone Pictures)

All of my fellow Maryland teens and I liked “Step Up” because it was set in Baltimore, had cool dancing, and starred 2000s heartthrob Channing Tatum, who also appeared in “She’s the Man.” Tyler Gage (Tatum), a street dancer from the wrong side of the tracks, is sentenced to perform community service cleaning the prestigious Maryland School of the Arts after he and his friends vandalize it. He gets roped into a showcase with ballerina Nora (Jenna Dewan), learning about discipline and self-control while opening Nora’s eyes to the world outside her dance studio.

But like many films in this list, we only surface-watched “Step Up” as teens, not fully appreciating the social and economic issues it was trying to drive home. While we might have taken away some of the messages about overcoming challenges through discipline, staying headstrong in the face of negative influences, and bridging gaps through creativity, we probably weren’t mature enough yet to enact them. Now, it’s easy to find Tyler’s story relatable and for us to begin to think about the areas of our lives that could benefit from a similar transformational journey.

“Step Up” is streaming on Amazon Prime.

‘Juno’ (2007)

A man and a pregnant girl talk on a couch in this image from Fox Searchlight Pictures.
“Juno” was one of the smartest teen films of the 2000s. (Image: Fox Searchlight Pictures)

You may think the cringe comedy “Juno,” a film about navigating a pregnancy in high school, shows a niche teen experience, but the six pregnancies in my graduating class would disagree. At the time, cool girl Juno (Elliot Page) seemed especially real, with her monotone, snarky, Academy Award-winning dialogue and atypical confidence acting as a sharp contrast to other teen-girl protagonists of the time. The film got flack from both sides of the abortion debate, but the filmmakers have described its message as “pro-adulthood,” which makes it easier to see the truth as an adult.

Despite all of the emotional turbulence going on around her, Juno is forced to make all of the hard decisions by the adults in her world, which she consistently does in pursuit of the kind of life she wants — making her an unusual but important role model for teens. It’s also easier now for me to see Vanessa (Jennifer Garner) and Mark (Jason Bateman), the prospective adoptive parents, as they were intended, putting the full responsibility for things going haywire on Mark’s insecurities rather than reading Vanessa as a stifling control freak as many teens did.

It was also in large part due to the influence of this movie that we all spent our college years in flannel shirts playing indie songs “you wouldn’t have heard of” on our acoustic guitars, so thanks for that.

“Juno” is available on Hulu.

‘Twilight’ (2008)

A teen girl and boy have dinner at a restaurant in this image from Summit Entertainment.
“Twilight” took teen culture by storm and created a generation of Twihards. (Image: Summit Entertainment)

Probably the most divisive title on this list, “Twilight” was a vampire romance sensation that dominated pop culture for half a decade. While they got flack at the time, the mumbling, moping teens of Forks High were pretty realistic. Plus, the aforementioned Stewart believably acted like she was in love with a hyper-controlling dead person, the moody cinematography was a vibe, and the iconic indie soundtrack helped usher in a mainstream breakthrough for the genre.

In the years since it came out, the story of Bella Swan (Stewart) moving to Washington and falling in love with handsome vampire Edward Cullen (Robert Pattinson) has been thoroughly broken down for all the reasons it was unhealthy, so we know to expect that toxicity watching as adults. In fairness, romanticizing toxic relationships was kind of a thing back in the day, from “Heathers” to “The Phantom of the Opera.”

As grown-ups, though, it’s easier to see the mental health metaphors the characters represent, from Edward’s preoccupation with death to Bella’s lack of self and her codependency. Also, many of us hadn’t ever been in love yet on our first watch, so it’s easier now to relate to the characters’ desire to literally spend forever together. Just like when we were teens, the chill pacing and nature-heavy visuals make for a calming escape today.

“Twilight” and its sequels are available to stream on Hulu.

Leave a Reply

Your email address will not be published.