What To Watch
14 Movies and Shows Starring Iconic Millennial Actors
Put on your best Hannah Montana wig and never let go of your nostalgia, Jack.
By Ashley Lee and Caitlin Busch
March 24, 2026
14 Movies and Series Starring Millennial Actors Like Miley Cyrus, Emily Osment, and More - Netflix Tudum
Every generation claims to have had the best childhood, but millennials actually did. Raised on Total Request Live, Game Boys, Flintstones vitamins, and Lunchables, we got to grow up with the best of both worlds: playing outside and clicking around on a computer screen, complete with dial-up internet access, downloadable music, and the good ol’ Oregon Trail. And we were shaped by iconic movies and shows starring the likes of Lindsay Lohan, Freddie Prinze Jr., Miranda Cosgrove, Zac Efron, Miley Cyrus, Rachael Leigh Cook, and Brenda Song.
Thankfully, Netflix has plenty of new adventures with old friends from the ’90s and the early aughts: slasher flicks with familiar faces, romantic comedies where our high school crushes find love as adults, and dramas featuring issues millennials hold dear. Stream any of these 14 titles for another good time with a decades-old friend or two.
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I Know What You Did Last Summer
Back in 1997, Jennifer Love Hewitt, Freddie Prinze Jr., and Sarah Michelle Gellar became millennial royalty when they starred in the era’s quintessential teen slasher flick, as a group of friends who get stalked after covering up a hit-and-run accident. The actors reprise their roles in a new movie of the same name; this time, the teens in question are played by Tyriq Withers, Chase Sui Wonders, and Madelyn Cline. Elsewhere on Netflix, Gellar is in the dark comedy series Do Revenge and Prinze leads the holiday title Christmas with You.
A Tourist's Guide to Love
Rachael Leigh Cook won our hearts in 1999 when she starred in the high school rom-com She’s All That, as well as the 2001 music industry comedy Josie and the Pussycats. Fall in love with her all over again by watching A Tourist’s Guide to Love, a globetrotting romance in which she plays a travel executive who goes undercover on a group tour with a free-spirited expat guide. Make it a double feature with the rom-com Love, Guaranteed, in which she plays an attorney whose stubborn client tries to sue a popular dating site.
Don't Look Up
Before Leonardo DiCaprio became an Academy Award winner and a vocal environmentalist, he was the reigning hunk of the ’90s, making viewers swoon in Romeo + Juliet and Titanic. (Real ones knew he’d be big from his role in the family sitcom Growing Pains, and still appreciate both of his performances in The Man in the Iron Mask.) In Don’t Look Up, DiCaprio is in panic mode as an astronomer who goes on a media tour to warn humankind of a fatal comet that’s hurtling toward Earth. Jennifer Lawrence, Jonah Hill and Meryl Streep also appear in the political satire.
Running Point
Back in the ’00s, the Disney Channel belonged to Brenda Song. Besides playing the hotel heiress London Tipton in The Suite Life of Zack & Cody, she also controlled the weather in The Ultimate Christmas Present, pranked a pop star in Stuck in the Suburbs, and saved the world in Wendy Wu: Homecoming Warrior. (Plus, she married Macaulay Culkin, the millennial poster child all grown up!) In the show Running Point, Song means business as the intimidating chief of staff of the Los Angeles Waves, the struggling basketball franchise that’s under new leadership. Song also stars in the psychological thriller Secret Obsession as a woman who wakes up with amnesia after a traumatic attack.
Irish Wish
The Parent Trap, Life-Size, Get a Clue, Freaky Friday, and Mean Girls are just some of the hit movies that crowned Lindsay Lohan as our millennial queen. (The real fans still know every word of her debut album single “Rumors.”) She’s in top form in Irish Wish as a book editor who travels to Ireland to watch her dream guy get married to her best friend, until a magical relic changes her reality and she wakes up as the bride-to-be. Want a holiday vibe? Lohan also leads the festive rom-coms Our Little Secret and Falling for Christmas.
Extremely Wicked, Shockingly Evil and Vile
Zac Efron rose to fame in the ’00s by singing in Hairspray, playing basketball in 17 Again, and singing and playing basketball in the High School Musical movies. He’s since shown amazing range on Netflix: hosting the travel series Down to Earth with Zac Efron, charming Nicole Kidman in the rom-com A Family Affair, and portraying the serial killer Ted Bundy in the drama Extremely Wicked, Shockingly Evil and Vile. The latter biopic also stars Lily Collins, Kaya Scodelario, and John Malkovich, and is based on the memoir of Bundy’s former girlfriend Elizabeth Kendall.
The Wrong Paris
After making her film acting debut in the comedy School of Rock and representing younger siblings everywhere in the series Drake & Josh, Miranda Cosgrove became the face of the internet as the star of Nickelodeon’s iCarly. In The Wrong Paris, she excitedly joins a dating show and anticipates its filming in France, only to discover that it’s actually taking place in Paris, Texas. For more Cosgrove, check out Mother of the Bride, in which she plays an influencer getting married at a glamorous Thailand resort while managing her parents and future in-laws.
The Power of the Dog
Kirsten Dunst was frequently on millennials’ screens, thanks to Interview with the Vampire, Jumanji, Drop Dead Gorgeous, Bring It On, and more. (And no matter how many Spider-Man remakes there are, she’ll always be our Mary Jane Watson.) Dunst earned an Oscar nomination for her performance in The Power of the Dog. She plays a single mother who gets married to a wealthy ranch owner, only to be tormented by her new brother-in-law. Dunst’s real-life husband, Jesse Plemons, is also in the Western drama, alongside Benedict Cumberbatch, Kodi Smit-McPhee, and Thomasin McKenzie.
Nobody Wants This
The reason millennials are famously great at researching every bestie’s blind date is because of Veronica Mars, starring Kristen Bell as the titular teen sleuth. (And as the salacious narrator of the teen soap Gossip Girl, she’s also the permanent voice in our heads.) In Nobody Wants This, Bell plays an agnostic sex podcaster who falls in love with a rabbi, played by fellow millennial mainstay Adam Brody. (The most fun millennial fact ever: Leighton Meester, who led Gossip Girl and is married to Brody in real life, has a memorable guest role in the hit romantic comedy series.)
When They See Us
Joshua Jackson left his mark on a generation as The Mighty Ducks’ ice hockey captain Charlie and the sarcastic Pacey in Dawson’s Creek — the teen soap also made Katie Holmes, James Van Der Beek, and Michelle Williams into household names. Jackson delivers a standout performance as a defense attorney in Ava DuVernay’s When They See Us, which is based on the true story of five teens falsely accused of a brutal attack in Central Park. Vera Farmiga, Aunjanue Ellis-Taylor, Niecy Nash, Felicity Huffman, John Leguizamo, and Michael K. Williams appear in the four-part miniseries.
Santa Clarita Diet
Drew Barrymore was the ultimate big-screen sweetheart in the early aughts, thanks to movies like The Wedding Singer, Ever After, Never Been Kissed, and Charlie’s Angels. She shows a much more primal — though always comedic — side in three seasons of Santa Clarita Diet. She plays a real estate agent, wife, and mother whose ordinary life is upended when she suddenly starts showing signs of turning into a zombie. Her husband and daughter try to make sense of her new condition, while dealing with nosy neighbors and trying to find a cure.
The Merry Gentlemen
Chad Michael Murray has made a career out of millennial heartthrob roles in Gilmore Girls, A Cinderella Story, House of Wax, and Freaky Friday. But he’s forever cemented in our hearts as One Tree Hill’s Lucas Scott, a high schooler with a love of literature and basketball who initially butts heads with the top jock, also his half-brother. He goes full holiday hottie in The Merry Gentlemen, playing a sarcastic contractor who takes the stage as a sultry dancer to help save the small town’s performing arts venue. For more Murray, throw on Mother of the Bride to see him woo Brooke Shields, or try the romantic drama series Sullivan’s Crossing.
Black Mirror
After she shed her Hannah Montana origins — including the blonde wig, sequined scarf, and Malibu beach house — Miley Cyrus built her own music career. She also didn’t lose the acting bug. In Season 5, Episode 3 (“Rachel, Jack and Ashley Too”) of the dystopian anthology series Black Mirror, the real-life Grammy winner stars as the fictional Ashley O, a pop superstar who longs to branch out. Her controlling manager will do anything to stop that from happening. It’s up to two girls (one teenage superfan and her rock-loving older sister) and a toy robot with Ashley’s personality to save the day in this episode, which includes covers of two Nine Inch Nails songs, including the hit “On a Roll.”
Pretty Smart
Emily Osment of Hannah Montana and Young & Hungry fame leads this sitcom as Chelsea, an exacting aspiring novelist who’s forced to move to Los Angeles and live with her sister, Claire (Olivia Macklin), after breaking up with her snooty professor boyfriend. While Chelsea initially judges Claire’s happy-go-lucky attitude and her lovably eccentric roommates — personal trainer Grant (Gregg Sulkin), spiritual healer Solana (Cinthya Carmona), and social media influencer Jayden (Michael Hsu Rosen) — she slowly realizes that she could learn a thing or two from all of them.
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