40 Must-Watch Movies for Millennials (Sorry, Boomers)

There are so many things we love about being a millennial. For one, we can speak to experiences like using a floppy disk and renting a Blockbuster movie. And of course, there’s the fact that we navigated a major shift in the world of technology. But the most rewarding part is getting to see all the iconic films that shaped our generation.

From contemporary titles that reflect our culture to coming-of-age classics that define our childhood, here are 40 must-watch millennial films.

The 25 Best High School Movies of All Time

1. ‘clueless’ (1995)

Cher (Alicia Silverstone) and her BFF embark on a mission to transform the new girl, Tai (Brittany Murphy), into a beauty queen. But things take a turn for the worse when Tai becomes popular.

2. ‘mean Girls’ (2004)

From Karen’s (Amanda Seyfried) psychic abilities to Gretchen’s (Lacey Chabert) determination to make “fetch” happen, this brilliant coming-of-age comedy is a cultural masterpiece—one that’s sure to resonate with anyone who has stepped foot inside of a high school.

3. ‘the Devil Wears Prada’ (2006)

There’s one major reason to watch this movie: Meryl Streep. Her role as Andy Sachs’s (Anne Hathaway) demanding boss, Miranda Priestly (also a fictionalized version of Vogue editor, Anna Wintour), is basically the highlight of the entire movie, which also offers a valuable lesson on persistence.

4. ‘romy & Michele’s High School Reunion’ (1997)

BFFs Romy (Mira Sorvino) and Michele (Lisa Kudrow) create a huge web of lies in an attempt to impress their old classmates at a high school reunion. Even with its silly tone, this movie brilliantly touches on the common struggle of feeling inadequate in comparison to your successful peers.

5. ‘bring It On’ (2000)

The iconic film follows rival cheerleading squads as they strive to beat each other at nationals, all while addressing relevant issues like white privilege and cultural appropriation.

6. ‘never Been Kissed’ (1999)

First kisses can be so nerve-wracking, and budding journalist Josie Geller (Drew Barrymore) knows the feeling all too well. After agreeing to go undercover as a high school student for a story, Josie falls for her dreamy teacher. But will she get her first kiss? (We know, it sounds creepy, but just roll with it).

7. ‘love And Basketball’ (2000)

Childhood BFFs Monica (Sanaa Lathan) and Quincy (Omar Epps) are both eager to become professional basketball players. But as they grow older, they’re forced to choose between their careers and their friendship.

8. ‘miss Juneteenth’ (2020)

If you’re drawn to mother-daughter relationships and Black womanhood, you have to add this one to your queue. Miss Juneteenth centers around a single mom and former beauty pageant winner, who wants her 15-year-old daughter to follow in her footsteps, even though her daughter isn’t too thrilled about the idea.

9. ‘reality Bites’ (1994)

Navigating the real world is no easy feat, as demonstrated by college grad Lelaina (Winona Ryder) and her group of friends. The aspiring filmmaker documents her post-university life as she struggles to find her place in the world.

10. ‘legally Blonde’ (2001)

In this feminist masterpiece, Elle Woods (Reese Witherspoon) attends Harvard for the sole purpose of winning back her ex-boyfriend. But when she starts to excel, she learns that there’s far more to her than her fabulous looks.

11. ‘mrs. Doubtfire’ (1993)

Robin Williams shines as divorced Daniel Hillard, who hatches an over-the-top plan to spend more quality time with his children. This includes adopting a new persona and fooling his ex-wife into hiring him as a nanny—but it only lasts for so long.

12. ‘the Parent Trap’ (1998)

When thinking of quintessential millennial movies that defined our childhood, The Parent Trap comes to mind. Because watching Hallie and Annie (Lindsay Lohan) mess with Meredith Blake is pure entertainment.

13. ‘frances Ha’ (2013)

Female friendships, sexuality and the challenges of transitioning into adulthood are all themes that get explored in this dramedy, which follows a millennial who’s trying to make it as a dancer in New York.

14. ‘save Yourselves’ (2020)

A couple in their 30s decide to unplug from their busy lives and reconnect with one another by traveling to a remote cabin. There’s just one problem: The rest of the world is under attack, and they haven't the slightest clue.

15. ‘boyhood’ (2014)

This poignant coming-of-age film follows the life of Mason Evans Jr. (Ellar Coltrane). Spanning from ages six through eighteen, it shows how Mason’s experiences are impacted by his divorced parents.

16. ‘inside Out’ (2015)

When young Riley moves with her family to a new city, her personified emotions (including Joy, Sadness, Anger, Fear and Disgust) try to guide her through the transition, but it’s more difficult than they thought.

17. ‘harry Potter And The Sorcerer's Stone’ (2001)

Harry (Daniel Radcliffe), Ron (Rupert Grint) and Hermione (Emma Watson) essentially grew up right along with us, and it certainly didn’t hurt that they live in a magical world. Anyone else still waiting on their acceptance letter from Hogwarts?

18. ‘the Fast And The Furious’ (2001)

It's the franchise that made us fantasize about speeding along an open road in a Ford Mustang. In the film, Dominic (Vin Diesel) takes Brian (Paul Walker), a newbie racer, under his wing with zero knowledge that he’s actually an undercover cop.

19. ‘scream’ (1996)

This star-studded satirical slasher follows a teenager and her friends as they get terrorized by a mysterious killer in a ghost mask. The balance of smart humor and suspense practically makes this one required viewing.

20. ‘spider-man’ (2002)

Seeing Peter Parker (Tobey Maguire) try to navigate his newfound superpowers (and of course, that iconic upside-down kiss) never gets old.

21. ‘the Social Network’ (2010)

Jesse Eisenberg, Andrew Carfield and Justin Timberlake star in this spicy drama, which tells the origin story of Facebook, a social platform that helped shape the millennial generation.

22. ‘anchorman’ (2004)

Arguably Will Ferrell’s best movie to date, this comedy follows Ron Burgundy, a successful anchorman who starts a bitter feud with the new female anchor. Expect silly humor and countless quotable one-liners.

23. ‘she’s All That’ (1999)

Yes, the story line is seriously problematic (more on that here), but this rom-com is a pop culture phenomenon. A popular jock named Zack (Freddie Prinze Jr.) agrees to a risky bet after his ex-girlfriend dumps him for a reality star.

24. ‘forrest Gump’ (1994)

A series of historical events are seen through the eyes of a kind-hearted, yet dim-witted, Alabama man named Forrest Gump (Tom Hanks). Although he gains recognition for his hard work and enthusiasm, he only cares about one thing: his childhood crush, Jenny (Robin Wright).

25. ‘lady Bird’ (2017)

High school senior Christine McPherson (Saoirse Ronan), who goes by "Lady Bird," has dreams of going away to college, and she’s determined to make this happen—despite her strong-willed mom and her family’s limited funds.

26. ‘juno’ (2007)

When 16-year-old Juno MacGuff (Elliot Page) discovers that she’s pregnant by her best friend, Paulie Bleeker (Michael Cera), she’s forced to make a series of lifechanging decisions. While it tackles serious subject matters, this Oscar-winning title is incredibly witty and lighthearted.

27. ‘pretty Woman’ (1990)

Starring Julia Roberts, AKA the queen of ’90s rom-coms, Pretty Woman follows a businessman (Richard Gere), who falls in love with a young prostitute (Roberts).

28. ‘how To Lose A Guy In 10 Days’ (2003)

Kate Hudson plays Andie, a writer who’s tasked with penning a how-to story about what not to do in a relationship. Her plan turns to utter chaos when she meets a cocky ladies’ man (Matthew McConaughey), who’s determined to win her heart.

29. ‘how Stella Got Her Groove Back’ (1998)

While vacationing with her friend in Jamaica, 40-year-old Stella (Angela Bassett) starts a casual fling with a gorgeous young man in his 20s. But when she prepares to return home, she realizes that she’s actually falling in love with him.

30. ‘do The Right Thing’ (1989)

When the Black community confronts a pizzeria owner about the lack of diversity on his "Wall of Fame," racial tensions run very high. It's been more than three decades since the film was made, but the themes of police brutality, racial division and gentrification make it feel even more relevant today.

31. ‘the Breakfast Club’ (1985)

This follows six teens from different cliques as they spend their Saturday in detention. Fortunately for them, their day of punishment eventually takes a turn for the better. *Cue “Don’t You (Forget About Me)” by Simple Minds*

32. ‘the Craft’ (1996)

Loved Mean Girls? Well, meet the movie’s edgier big sister, The Craft. High schooler and new girl Sarah (Robin Tunney) joins a group of outsiders and pursues witchcraft. As a result, she has to deal with the unfortunate consequences.

33. ‘10 Things I Hate About You’ (1999)

Bianca (Larisa Oleynik), aka the most popular girl in school, wants go out with a boy that she likes. The only problem? She can’t date until her tightly-wound big sister, Kat (Julia Stiles), finds someone. Feeling desperate, she hires bad boy Patrick (Heath Ledger) to win Kat's heart. What could go wrong?

34. ‘brown Sugar’ (2002)

Meet Andre (Taye Diggs) and Sidney (Sanaa Lathan), two longtime friends who realize they have feelings for each other. FYI: Hip-hop lovers are in for a treat with the film’s soundtrack.

35. ‘set It Off’ (1996)

Jada Pinkett Smith, Vivica A. Fox, Kimberly Elise and Queen Latifah star as four Black women who rob banks to counteract their financial struggles. While the heist film is action-packed, it also speaks to multiple relevant issues, including police violence and misogynoir.

36. ‘drumline’ (2002)

Movies that focus on Black colleges and universities are few and far between. But Drumline stands out for its depiction of college life and, of course, Nick Cannon’s standout performance.

37. ‘sisterhood Of The Traveling Pants’ (2005)

Ann Brashares’s novel comes to life in this brilliant, lighthearted dramedy about four best friends, who maintain their tight-knit bond through a stylish pair of jeans that fits them all perfectly.

38. ‘friday’ (1995)

Set in South-Central L.A., Craig (Ice Cube) and his best friend Smokey (Chris Tucker) decide to spend their day hanging out on his front porch. From drive-by shootings to run-ins with talkative neighbors, Craig and Smokey get a whole lot more than they bargained for.

39. ‘booksmart’ (2019)

Overachieving best friends Amy (Kaitlyn Dever) and Molly (Beanie Feldstein) realize that while they have the perfect grades, they’ve missed out on all the fun parties that make high school so special. Determined to have some fun before graduation, they decide to let loose for one night (and naturally, chaos ensues).

40. ‘brokeback Mountain’ (2005)

Set in Wyoming during the ’60s, a one-night stand between cowboys Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal) turns into a passionate love affair that spans for two decades—even after they marry other people.