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15 Celebrity Crushes from Millennial Movie and Music Memories

By Teddy Danielson · Edited edition:

Edited by The Nostalgic Millennial

Original publication and manuscript receipt dates are not established.

Orange-red neon letters read “I HAVE A CRUSH ON YOU” against a dark wall.
Orange-red neon sign in a photograph by Leonardo Sanches. Image: Leonardo Sanches / Unsplash

Remember how your bedroom walls could disappear behind a collection of posters? Teen magazines supplied the pictures, interviews and movie previews. A new film or music video could mean finding space for another face above the desk.

Everyone's list was different. These 15 stars bring back some of the movies, songs and TV shows that filled those years, from the older millennial rental-store favorites to the younger generation's Disney soundtracks.

The portraits are dated in their captions. They show the people at the stated dates, rather than recreating their earlier screen roles.

Brad Pitt

Tristan in Legends of the Fall, Tyler Durden in Fight Club, Rusty Ryan in Ocean's Eleven: Brad Pitt supplied several very different candidates for the bedroom wall. A romantic drama, a disturbing fight-club story and a heist film could all lead back to the same actor.

The magazine coverage extended beyond those roles. His past marriages to Jennifer Aniston and Angelina Jolie were part of that public story, too. But for a rewatch, it's the films that give you somewhere to start. AFI's filmography lists the roles and credits.

Brad Pitt in an adult portrait.
Brad Pitt at the 2024 Venice International Film Festival. Resized; metadata removed. Image: Harald Krichel / WikiPortraits · CC BY-SA 4.0

Natalie Portman

Mathilda in Léon: The Professional was an early Natalie Portman role. Queen Amidala's costumes in Star Wars later offered enough material for a mood board of their own. Garden State and V for Vendetta took her into different settings again.

Her university years were also part of the magazine profile. Portman graduated from Harvard in 2003 with a degree in psychology. Harvard's account of her 2015 Class Day address recalls those years in her own words.

Natalie Portman in an adult portrait.
Natalie Portman at the 2026 Sundance Film Festival. Resized; metadata removed. Image: Colleen Sturtevant / WikiPortraits · CC BY 4.0

Leonardo DiCaprio

Romeo + Juliet and Titanic made quite a double bill. There was the floppy hair, the soundtrack and Jack Dawson at the bow of the ship: “I’m the king of the world!” AFI's Titanic record includes the line.

DiCaprio's later work and environmental advocacy gave fans other reasons to follow his career. In 2014, the United Nations designated him a Messenger of Peace with a focus on climate change. A poster, a soundtrack CD or a much-replayed VHS might still be the first thing those early films bring to mind.

Leonardo DiCaprio stands at a lectern during a public conference.
Leonardo DiCaprio speaking at the 2016 Our Ocean Conference in Washington, D.C. Resized; metadata removed. U.S. government work; public domain in the United States. Image: U.S. Department of State

Mila Kunis

Jackie's sharp remarks on That '70s Show made Mila Kunis a familiar face on television. Forgetting Sarah Marshall and Black Swan later put her in very different films.

Then there's Meg on Family Guy. A voice can bring back a TV memory as quickly as a magazine cover. FOX's cast biography connects that voice role with the live-action work.

Mila Kunis in an adult portrait.
Mila Kunis at the 2025 world premiere of Wake Up Dead Man: A Knives Out Mystery. Resized; metadata removed. Image: Max Surprenant / WikiPortraits · CC BY 4.0

Keanu Reeves

Bill & Ted, Speed and The Matrix gave Keanu Reeves three routes into the poster collection. A time-travel comedy, a bus thriller and Neo's black coat belonged to different movie nights.

The slow-motion action in The Matrix is easy to picture years later. Neo's kung-fu scene and black coat gave fans plenty to remember. AFI's filmography is a useful guide to the screen roles.

Keanu Reeves in an adult portrait.
Keanu Reeves at the 2025 Toronto International Film Festival. Cropped on Commons; resized; metadata removed. Image: Gabriel Hutchinson / WikiPortraits · CC BY-SA 4.0

Liv Tyler

Corey in Empire Records came with a record-shop setting worth daydreaming about. The film's cast listing credits Liv Tyler in that role. Armageddon supplied a tearful farewell, while The Lord of the Rings brought Arwen into the picture.

Tyler is Aerosmith singer Steven Tyler's daughter. Her screen father in Armageddon is Harry Stamper, played by Bruce Willis; Tyler plays Grace. Criterion's essay on the film describes that father–daughter story. Its edition also includes the Aerosmith video “I Don’t Want to Miss a Thing.”

Liv Tyler in an adult portrait.
Liv Tyler in a portrait dated September 18, 2016. Cropped on Commons; resized; metadata removed. Image: Walterlan Papetti · CC BY-SA 4.0

Justin Timberlake

The *NSYNC videos, coordinated outfits and much-discussed curls are part of the late-'90s picture. Justified and FutureSex/LoveSounds then supplied music for a different stage of the 2000s.

His Saturday Night Live work with Andy Samberg added comedy to the list. The Television Academy's 2007 song-writing credits record their work together. For some fans, the boy-band poster came first; for others, it was a song burned onto a mix CD.

Justin Timberlake in a patterned shirt at a public event, with other people behind him.
Justin Timberlake at the 2016 San Diego Comic-Con International. Resized; metadata removed. Image: Gage Skidmore · CC BY-SA 2.0

Jennifer Love Hewitt

Sarah Reeves in Party of Five gave viewers a TV drama to follow. I Know What You Did Last Summer and its sequel supplied horror-film nights with friends. Can't Hardly Wait added a high-school party to the watchlist.

Jennifer Love Hewitt's AFI filmography includes Julie James in the two horror films and Amanda in Can't Hardly Wait. Those roles cover several corners of a late-'90s video-store shelf.

Jennifer Love Hewitt in an adult portrait.
Jennifer Love Hewitt in a photograph dated May 14, 2018. Cropped on Commons; resized; metadata removed. Image: Greg2600 · CC BY-SA 2.0

Matthew McConaughey

“Alright, alright, alright.” The line belongs to Wooderson in Dazed and Confused, before the early-2000s romantic comedies. Focus Features revisits the scene in its anniversary feature.

The Wedding Planner, How to Lose a Guy in 10 Days and Failure to Launch make a separate McConaughey watchlist. If your memory of the period involves a rental-store trip and a debate over which rom-com to choose, one of those titles may have won.

Matthew McConaughey in an adult portrait.
Matthew McConaughey at the 2025 Toronto Film Festival. Cropped on Commons; resized; metadata removed. Image: Gabriel Hutchinson / WikiPortraits · CC BY-SA 4.0

Hayden Panettiere

“Save the cheerleader, save the world.” For viewers of Heroes, the phrase brings back Claire Bennet and a particular era of television. Hayden Panettiere also appeared in Remember the Titans and Bring It On: All or Nothing.

Claire's story gave sci-fi fans a character to follow from week to week. A favorite TV character could earn space in the magazine collection just as quickly as a movie lead. The Television Academy's contemporary presenter announcement identifies Panettiere with the role.

Hayden Panettiere holds a microphone in front of a Fan Expo backdrop.
Hayden Panettiere at Fan Expo in Toronto in 2011. Resized; metadata removed. Image: Tabercil · CC BY-SA 2.0

Will Smith

The Fresh Prince of Bel-Air, Independence Day and Men in Black bring together sitcom reruns and big-screen alien encounters. Smith could turn up in the afternoon TV schedule and the weekend cinema plans.

His music adds another way back to the period. Your strongest memory might be the Fresh Prince theme rather than a poster. For a film night, Sony's Men in Black page credits him as Jay.

Will Smith sits behind microphones at a convention panel.
Will Smith speaking at the 2017 San Diego Comic-Con International. Resized; metadata removed. Image: Gage Skidmore · CC BY-SA 2.0

Jessica Alba

Dark Angel introduced Jessica Alba as Max Guevara, a genetically enhanced soldier. The series synopsis gives Max's name and dates the show to 2000.

Sin City and Fantastic Four later offered different comic-book screen settings, with Alba playing Nancy and Sue Storm. Those roles make useful landmarks for remembering which show or film first caught your attention.

Jessica Alba smiles beside a microphone at a convention panel.
Jessica Alba speaking at the 2014 San Diego Comic-Con International. Resized; metadata removed. Image: Gage Skidmore · CC BY-SA 2.0

Johnny Depp

Edward in Edward Scissorhands and Captain Jack Sparrow in Pirates of the Caribbean were two distinctive screen characters. The makeup, costumes and performances gave fans very different images to remember.

For a collection that leaned toward fantasy and offbeat characters, either film could fit. Disney's account of The Curse of the Black Pearl records Depp's Captain Jack role and the film's 2003 release.

Johnny Depp in an adult portrait.
Johnny Depp at the 2020 Berlin International Film Festival. Cropped on Commons; resized; metadata removed. Image: Harald Krichel · CC BY-SA 3.0

Kate Hudson

Penny Lane in Almost Famous put Kate Hudson in a film full of music, touring and backstage encounters. She received a supporting-actress nomination for that role at the 2001 Academy Awards.

How to Lose a Guy in 10 Days offers another familiar entry, alongside Matthew McConaughey. A film soundtrack and a rom-com rental can hold equally strong memories, even when they occupied different shelves.

Kate Hudson in an adult portrait.
Kate Hudson at the 2024 Toronto International Film Festival. Resized; metadata removed. Image: Kevin Payravi / WikiPortraits · CC BY-SA 4.0

Zac Efron

High School Musical put Zac Efron at the center of a Disney musical as Troy Bolton. Disney's program history dates its premiere to January 20, 2006.

Later films included the comedy Neighbors in 2014 and the musical The Greatest Showman in 2017. They belong to a later part of the career, rather than the '90s or early 2000s. For younger millennials, the High School Musical soundtrack may be the starting point.

Zac Efron in an adult portrait.
Zac Efron on the red carpet at the 2012 Toronto International Film Festival. Resized; metadata removed. Photographer’s signature retained. Image: Jason Hargrove · CC BY-SA 2.0

Who was on your wall?

An old poster can bring back the rest of a room: the CD player, a school bag on the floor and the magazine the picture came from. Comparing those memories leaves room for different ages, tastes and favorites.

Pick a film or album from your own collection and revisit it. If the clothes in those old pictures catch your eye, our look back at 12 '90s fashion trends offers another trip through the same years.

A pink-red paper heart hangs from string with a wooden clothespin against a dark blue-gray background.
Paper heart clipped to string in a stock photograph. Image: Jess Bailey Designs / Pexels