The term, “millennial,” means a lot of different things to different people. Whether it’s other generations calling them out as the group of “participation trophies” or being blamed for economic failures because of too much avocado toast, there seems to regularly be a negative connotation to the word. Regardless, millennials have been an incredibly important part of pop culture and entertainment, and some of the best movies for millennials reflect that.
They have helped make the film industry a more inclusive place for the outliers of the world, and have also been more influenced by movies than previous generations. They grew up with some of the first openly gay theatrical releases, deeply dark and insidious characters, and among generation-defining millennial movies that birthed some of the most iconic characters of all time.
Updated on July 14, 2023 by Hannah Saab:
There’s no shortage of legendary movies that define millennials and continue to influence popular culture to this day, with the upcoming Toy Story 5 just among the latest examples of the far-reaching impact these films have. Whether it’s through incorporating unique slang, influencing fashion choices, and, most importantly, capturing the times and the vibe that came with them, some movies just manage to sum up millennials as a generation.
17 ‘Twilight’ (2008)
The Twilight frenzy of 2008 came about at the perfect time in millennial life. “Scene” fashion was in, Myspace was at its peak, and music was all about crooning and emo hairstyles. The movie’s triumph even brought about an entire wave of vampire and werewolf television shows that were highly successful as well, like The Vampire Diaries, Teen Wolf, and True Blood.
It may be among millennials’ favorite movies, but Twilight is in no way the peak of cinema. But it resonated with millennials in the same way that the Harry Potter franchise did. Following the plain and awkward Bella Swan, the movie takes you on an escapist journey where its ordinary main character is sought after by a handsome 100-year-old vampire and a shirtless werewolf. What’s not to like?
16 ‘The Blair Witch Project’ (1999)
The Blair Witch Project created an entirely new way of movie marketing. It also pushed the found-footage horror genre to the front seat of pop culture. If you are a millennial, the memories of The Blair Witch Project’s release are probably still burned into your mind. It was hard to escape the movie when it was marketed as a “true story” and one of the scariest movies ever made.
The end scene where Mike is standing in a corner facing the wall, and Heather is attacked by the demonic entity while her camera falls, is one of the most memorable endings of all time. Rumors of it being based on a true story and actual found footage definitely didn’t help put anyone to sleep at night either.
15 ‘Clueless’ (1995)
Before Mean Girls, there was Clueless, which toes the line between millennial and Gen X movies. Alicia Silverstone is unforgettable as Cher Horowitz, a gorgeous, popular, and remarkably brilliant protagonist who befriends newcomer Tai Frasier (played by Brittany Murphy).
Inspiring new fashion trends and influencing slang, Clueless is an iconic ’90s film any millennial should watch at least once. The true star, of course, is Cher, who subverts harmful stereotypes by showing genuine compassion, a surprising level of introspection, and unmatchable wit and sass.
14 ‘Easy A’ (2010)
An iconic Emma Stone role any millennial would recognize, she plays Olive Penderghast in the beloved teen movie, Easy A. Showing a specific brand of high school hell, the film depicts Olive’s experiences after gossip about her lie of losing her virginity spreads like wildfire and gives her a brand new reputation.
Olive’s reaction to her notoriety reflects rapidly changing opinions and discussions around sex and sexuality, which were still extremely taboo, especially among more conservative schools. Easy A also depicted an important shift in the way gossip spreads in high schools, as social media makes it extremely hard to hide secrets.
13 ‘Mean Girls’ (2004)
Before Mean Girls, Tina Fey was known as the nerdy comedian on Saturday Night Live with a quick wit and a killer pair of glasses. After the movie was released, audiences acknowledged her brilliant humor, and she went on to become one of the most well-known comedians in film.
Between Fey’s stellar screenplay, one of Lindsay Lohan‘s best performances, and Rachel McAdams’ turn as a wicked queen bee – the iconic millennial movie culminated as the perfect combination of teenage angst, realism, and comedy. The movie was dedicated to poking fun at cruel female high school bullies and fusing it with the toxic celebrity culture and unattainable beauty standards of the time.
12 ‘Garden State’ (2004)
Garden State is synonymous with the angsty indie movie soundtracks of the early 2000s. Zach Braff explored the struggles of young love and life through music in his directorial debut, which helped the movie achieve cult status among millennials.
While the movie is a rom-com, it completely blew any romance movie stereotypes out of the window. Garden State follows Andrew, who returns to his tiny hometown to attend his mother’s funeral. While there, he is confronted by various aspects of a life he thought he had forgotten. The laid-back and realistic characters resonated with millennials in a way that most major movie releases hadn’t before.
11 ‘Superbad’ (2007)
Superbad is the quintessential awkward high school movie for millennial guys. Starring Jonah Hill and Michael Cera as Seth and Evan, the hilarious coming-of-age film is centered on the students’ experiences as they vow to lose their virginity before graduating from high school. This soon proves to be a real challenge.
From the perfect chemistry between the two leads to the witty humor throughout the film, there’s more than one reason to love this movie. It reflects a kind of high school experience without the modern pressures of social media and gadgets, and transports millennials back to a time when they felt they were facing huge problems as teenagers (they weren’t).
10 ‘500 Days of Summer’ (2009)
A love story that’s never missing from discussions of classic millennial movies, 500 Days of Summer is a rom-com that stars Joseph Gordon-Levitt as Tom Hansen, who revisits his failed relationship with Zooey Deschanel‘s Summer Finn. Through a non-linear structure, the film depicts the romantic connection that builds and then fizzles out between the two unforgettable characters.
The movie credited for the “manic pixie dream girl” aesthetic, 500 Days has since been criticized for Summer’s characterization. It’s often misinterpreted in Tom’s favor, when really, it was a lopsided love story to begin with that illustrated two individuals with wholly different views and goals in a relationship. Back then, though, millennials were in it for the tears, dreamy color palette, and killer soundtrack.
9 ‘Brokeback Mountain’ (2005)
Brokeback Mountain was one of the first movies to break ground in mainstream LGBTQ+ cinema. It was also one of the first openly queer movies to be nominated for multiple Academy Awards. The movie followed rodeo cowboy, Jack, and ranch hand, Ennis, two men hired as sheep herders in Wyoming in 1963. One night on the mountain, Jack makes a drunken pass at Ennis, and the men fall in love while having to hide it from the world.
The movie shattered all types of stereotypes and masculine gender roles with its gay, rugged, cowboy characters. Heath Ledger and Jake Gyllenhaal were two of the biggest actors at the time as well, which helped usher curious millennials to the big screen to watch the tragic love story unfold in one of the best LGBTQ+ movies of all time.
8 ‘The Social Network’ (2010)
Most millennials remember when Facebook took over social media. Facebook was invite-only at first, and only students in university could use it. The floodgates opened once it was available to the entire public though, and people realized that Mark Zuckerberg had created a life-changing way to connect with family and friends.
This is precisely why David Fincher adapted Zuckerberg’s perilous story into a generation-defining film. One of the most popular millennial movies, The Social Network tells the behind-the-scenes troubles that Zuckerberg went through while producing the website, and it became a masterpiece of a tech CEO’s origin story.
7 ‘Titanic’ (1997)
Titanic was a life-changing film for many millennials who would go on to become obsessed with the tragic ship sinking. James Cameron created one of the most expensive and masterful sea epics in cinema, and it was even the #1 highest-grossing movie of all time for decades – earning $2 billion.
The sheer size of the three-hour-long journey from happiness to utter distress was new to many movie-goers at the time. There was a moment in time after the movie was released when Celine Dion‘s “My Heart Will Go On” played nonstop on radios across the country, co-workers and friends would brag about seeing it multiple times in theaters, and every show on television was spoofing it.
6 ‘Donnie Darko’ (2001)
Meeting Frank the Rabbit in Donnie Darko is a defining moment in many millennials’ lives. Donnie Darko came out around the time of the goth and alternative style resurgence in the early 2000s and helped usher in a generation infatuated with all things dark and gloomy.
The dark fantasy film follows a teenager named Donnie Darko as he sleepwalks outside of his home one night and sees a demonic-looking rabbit named Frank. Frank tells him that the world will end in 28 days, and strange things begin happening to Donnie. In his voyage to find out about his possible mental health conditions, Donnie became the poster child for every millennial who had ever felt alone or like an outsider.
5 The ‘Harry Potter’ Film Series (2001 – 2011)
Millennials likely still occasionally recount what it was like to excitedly line up for every new Harry Potter movie. Watching the titular character grow up alongside the audience is a rare phenomenon that can never be replicated again, as fans experienced the novels come to life before their very eyes.
To say that Harry Potter became a cultural phenomenon almost feels like an understatement, as it was so much more. Millennials could connect and bond with others over their shared love for the wizarding world, which created and defined its own space and earned a spot among the best movies of this generation.
4 ‘Toy Story’ (1995)
The Toy Story franchise needs no introduction. The legendary Disney film series enthralled young moviegoers with its 1995 movie, which introduced the world to beloved characters like Woody and Buzz. Every new entry in the series only seemed to get better, as the lessons became more profound and the characters more complex to keep up with the audiences’ changing lives and perspectives.
Toy Story 3 will forever be among millennials’ favorite movies, as it seemed like the perfect heartbreaking ending to Andy and Woody’s arc that the series had built up over the years. This tear-jerking goodbye serves as millennials’ poignant farewell to their own childhoods, too.
3 ‘The Matrix’ (1999)
The Matrix follows Neo, a man contacted by a mysterious woman who leads him into an underworld where existence is not what seems. He meets Morpheus, who asks him if he would like to take the blue pill – and remain oblivious to the Matrix, or the red pill, where he will “wake up” and fight a brutal battle against intelligent secret agents.
Since its release, the movie has changed so many facets of pop culture that it’s mind-blowing to think about. The red pill/blue pill situation has become synonymous with being controlled, the bullet time scene with Neo changed action effects forever, and directors, Lana and Lilly Wachowski, were some of the first trans directors to achieve such critical acclaim. The Matrix incorporated some of the most incredible choreography, effects, and themes in American cinema at the time.
2 ‘The Dark Knight’ (2008)
Heath Ledger‘s portrayal of the Joker in Christopher Nolan‘s second Batman film infiltrated the cultural zeitgeist in a way that had never been done before. The Dark Knight was a significant part of the millennial theatrical experience. Following the devastating death of Ledger before its release, the movie became a masterpiece in character study and comic book movies.
The Dark Knight is considered one of the best middle movies in any film trilogy, and it’s hard to imagine a film that is more defining of a generation. The movie made a then-record $158 million in its opening weekend, and sent forth a rise in Joker costumes and copycats for years. Aside from being one of the top millennial movies, the film also marked a switch within cinema, where audiences began to prefer less cartoonish movies.
1 The ‘Lord of the Rings’ Trilogy (2001 – 2003)
Among the best movies of our generation, J. R. R. Tolkien‘s fantastical universe came to the big screen through the massively successful Lord of the Rings trilogy. Following Frodo, Sam, Gandalf, and the rest of the Fellowship’s epic journeys, the three films used groundbreaking visual effects and flawless story arcs to keep viewers engaged year after year.
For millennials who have never seen anything like it before, this was their calling into the wide world of fantasy. It would spark conversations and begin groups that would endure, setting a new standard for what audiences expect to see in the fantasy genre.
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