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.
Millennials also 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. 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 and the new musical Mean Girls reboot 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)
Directed by Catherine Hardwicke
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 (Kristen Stewart), 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. And if the first one isn't enough of a bizarre treat already, there are four more in the saga to keep fans hooked. What's not to like?
Twilight
- Release Date
- November 20, 2008
- Director
- Catherine Hardwicke
- Cast
- Kristen Stewart , Robert Pattinson , Billy Burke , Peter Facinelli , Elizabeth Reaser , Cam Gigandet
- Runtime
- 120 minutes
16 'The Blair Witch Project' (1999)
Directed by Daniel Myrick and Eduardo Sánchez
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 (Michael C. Williams) is standing in a corner facing the wall, and Heather (Heather Donahue) 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. While it isn't as terrifying today given everyone knows it's not real, it still holds a certain appeal for those who experienced watching it when it first premiered.
The Blair Witch Project
- Release Date
- July 30, 1999
- Director
- Daniel Myrick , Eduardo Sánchez
- Cast
- Heather Donahue , Michael C. Williams , Joshua Leonard
- Runtime
- 81 minutes
15 'Clueless' (1995)
Directed by Amy Heckerling
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, wealthy, and remarkably brilliant protagonist who gains confidence after playing matchmaker at her shool. She soon befriends newcomer Tai Frasier (played by Brittany Murphy) and decides to give her a makeover, believing it will help her.
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.
Clueless
- Release Date
- July 19, 1995
- Director
- Amy Heckerling
- Cast
- Alicia Silverstone , Stacey Dash , Brittany Murphy , Paul Rudd , Donald Faison , Elisa Donovan
- Runtime
- 97 minutes
14 'Easy A' (2010)
Directed by Will Gluck
An incredible 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. Instead of shying away, Olive embraces her newfound infamy.
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.
Easy A
- Release Date
- September 16, 2010
- Director
- Will Gluck
- Cast
- Emma Stone , Penn Badgley , Amanda Bynes , Dan Byrd , Thomas Haden Church , Patricia Clarkson
- Runtime
- 92
13 'Mean Girls' (2004)
Directed by Mark Waters
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. Mean Girls 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. In the process, it defined an entire generation of teen girls who would go on to repeat the quotes and outfits for years to come.
Mean Girls (2004)
- Release Date
- April 30, 2004
- Director
- Mark Waters
- Cast
- Lindsay Lohan , Rachel McAdams , Tina Fey , Tim Meadows , Amy Poehler , Ana Gasteyer
- Runtime
- 97 minutes
12 'Garden State' (2004)
Directed by Zach Braff
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 Largeman (Zach Braff), a depressed, drug-using, failing actor, 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.
Garden State
- Release Date
- July 28, 2004
- Director
- Zach Braff
- Cast
- Zach Braff , Kenneth Graymez , George C. Wolfe , Austin Lysy , Gary Gilbert , Jill Flint
- Runtime
- 102
11 'Superbad' (2007)
Directed by Greg Mottola
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, and the duo will have to go through wacky events that test their bond before college.
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).
Superbad
- Release Date
- March 20, 2007
- Director
- Greg Mottola
- Cast
- Jonah Hill , Michael Cera , Christopher Mintz-Plasse , Bill Hader , Seth Rogen , Martha MacIsaac
- Runtime
- 113
10 '500 Days of Summer' (2009)
Directed by Marc Webb
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.
(500) Days of Summer
- Release Date
- July 17, 2009
- Director
- Marc Webb
- Cast
- Joseph Gordon-Levitt , Zooey Deschanel , Geoffrey Arend , Chloe Moretz , Matthew Gray Gubler , Clark Gregg
- Runtime
- 95
9 'Brokeback Mountain' (2005)
Directed by Ang Lee
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 Twist (Jake Gyllenhaal), and ranch hand, Ennis Del Mar (Heath Ledger), 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.
Brokeback Mountain
- Release Date
- September 10, 2005
- Director
- Ang Lee
- Cast
- Heath Ledger , Jake Gyllenhaal , Randy Quaid , Valerie Planche , Michelle Williams , Anne Hathaway
- Runtime
- 134 minutes
8 'The Social Network' (2010)
Directed by David Fincher
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 (as well as an effective if not scathing character study).
The Social Network
- Release Date
- October 1, 2010
- Director
- David Fincher
- Cast
- Jesse Eisenberg , Rooney Mara , Bryan Barter , Dustin Fitzsimons , Armie Hammer , Joseph Mazzello
- Runtime
- 120 minutes
7 'Titanic' (1997)
Directed by James Cameron
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, with Kate Winslet and Leonardo DiCaprio's legendary performances anchoring the narrative from start to finish. 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.
Titanic
- Release Date
- November 19, 1997
- Director
- James Cameron
- Cast
- Leonardo DiCaprio , Kate Winslet , Billy Zane , Kathy Bates , Frances Fisher , Gloria Stuart
- Runtime
- 194 minutes
6 'Donnie Darko' (2001)
Directed by Richard Kelly
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 (Jake Gyllenhaal) 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.
Donnie Darko
- Release Date
- October 26, 2001
- Director
- Richard Kelly
- Cast
- Jake Gyllenhaal , Holmes Osborne , Maggie Gyllenhaal , Daveigh Chase , Mary McDonnell , James Duval
- Runtime
- 113
5 The 'Harry Potter' Film Series (2001 - 2011)
Directed by Alfonso Cuarón, David Yates, Mike Newell, and Chris Columbus
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. That bond exists to this very day, with the thriving franchise still offering old and new fans chances to make meaningful connections.
Harry Potter
- Created by
- J.K. Rowling
- First Film
- Harry Potter and the Sorcerer's Stone
- Latest Film
- Harry Potter and the Deathly Hallows - Part 2
- Cast
- Daniel Radcliffe , Rupert Grint , Emma Watson
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. That said, nothing will compare to the first, at least in terms of nostalgic value. 1995's Toy Story can instantly transport any millennial back to their childhood and to simpler times.
Toy Story
- Release Date
- October 30, 1995
- Director
- John Lasseter
- Cast
- Tom Hanks , Tim Allen , Don Rickles , Jim Varney , Wallace Shawn , John Ratzenberger
- Runtime
- 81
3 'The Matrix' (1999)
Directed by The Wachowskis
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.
The Matrix
- Release Date
- March 31, 1999
- Director
- Lana Wachowski , Lilly Wachowski
- Cast
- Keanu Reeves , Laurence Fishburne , Carrie-Anne Moss , Hugo Weaving , Gloria Foster , Joe Pantoliano
- Runtime
- 136 minutes
2 'The Dark Knight' (2008)
Directed by Christopher Nolan
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 the superhero genre, where audiences began to prefer less cartoonish movies.
The Dark Knight
- Release Date
- July 18, 2008
- Director
- Christopher Nolan
- Cast
- Christian Bale , Heath Ledger , Aaron Eckhart , Michael Caine , Maggie Gyllenhaal , Gary Oldman
- Runtime
- 152 minutes
1 The 'Lord of the Rings' Trilogy (2001 - 2003)
Directed by Peter Jackson
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, LotR 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. Though it never managed to reach the same heights director Peter Jackson elevated it to, the franchise is still active and attracting a new generation of fans today.
The Lord of the Rings
- Created by
- J.R.R. Tolkien
- Latest Film
- The Hobbit: The Battle of the Five Armies
- First TV Show
- The Lord of the Rings: The Rings of Power