Since the late, great Robert Redford founded the Sundance Film Festival some four decades ago, the free-thinking, boundary-pushing showcase has attracted some of the world’s most lauded independent filmmakers, as well as the Hollywood heavyweights who populate their releases. However, unlike its glitzier European rivals, Cannes and Venice, Sundance is gloriously laid-back—think bare faces, chunky knits, and puffy coats instead of all-out glamour and floor-length ballgowns, and skiing and snowball fights in lieu of glittering galas.
Ahead of the 2026 edition of the festival, due to run from January 22 to 1 February—and the final one to be held in Utah’s snowy, picturesque Park City before its move to Boulder, Colorado—we revisit the best throwback photos from the ’90s and early aughts, from Mariah Carey cosplaying as a cowgirl to an incredibly poised, 13-year-old Kristen Stewart.
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A floppy-haired, Four Weddings and a Funeral-era Hugh Grant at Sundance with Elle MacPherson and John Duigan, their director for Sirens.
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A 22-year-old, pixie-cropped Winona Ryder sips a drink at Sundance to celebrate the premiere of Reality Bites.
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An 18-year-old Reese Witherspoon plays in the snow at Sundance.
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Debbie Harry and Liv Tyler promote James Mangold’s Heavy at Sundance.
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A 25-year-old Gwyneth Paltrow at the festival with her father, director Bruce Paltrow.
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Jawbreaker’s Rose McGowan and Rebecca Gayheart promote their instant cult classic, snow cones in hand, at Sundance.
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1999
Aussies Rose Byrne and Heath Ledger take a break from promoting their crime comedy film Two Hands.
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A 17-year-old Kirsten Dunst and 28-year-old Sofia Coppola at Sundance a year after they premiered The Virgin Suicides.
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A 25-year-old Christian Bale attends the festival for the premiere of American Psycho.
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The year she broke out with Almost Famous, a 20-year-old Kate Hudson trudges through the Sundance snow.
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A 29-year-old Matt Damon goes ultra casual for the premiere of Heather Graham’s Committed.
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A 13-year-old Emmy Rossum, wrapped up warm and posing in the snow, the year she made Songcatcher.
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Ethan Hawke, Uma Thurman, and Kyle MacLachlan at a dinner celebrating the Sundance release of Michael Almereyda’s modern retelling of Hamlet.
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Jennifer Connelly makes a case for double denim while promoting Waking the Dead.
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A 21-year-old Josh Hartnett, in an oversized knit with ruffled hair, at Sundance.
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Cyndi Lauper just wants to have fun (in the snow at Sundance).
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A 25-year-old Amber Valletta navigating the Park City snow.
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2000
Clea DuVall, Natasha Lyonne, and their moody pouts descend on Park City to promote their queer comedy But I’m a Cheerleader.
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RuPaul hugs Tammy Faye Bakker on Park City’s main drag.
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Christopher Walken hits the slopes while in town for the festival.
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A 23-year-old Maggie Gyllenhaal and a 20-year-old Jake Gyllenhaal pose for a family portrait in the snow ahead of the premiere of Donnie Darko.
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A year before she made Far From Heaven, Julianne Moore flashes a smile.
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Eight years before the release of (500) Days of Summer, a 19-year-old Joseph Gordon-Levitt and a 21-year-old Zooey Deschanel attended Sundance together for the premiere of their Jordan Melamed-helmed drama Manic.
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A 30-year-old Rachel Weisz at Sundance, promoting Beautiful Creatures.
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Cameron Diaz navigates the snow at Sundance.
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A 19-year-old Paris Hilton makes an entrance at a Hugo Boss party, as only she can.
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The year she starred in Save the Last Dance, a 19-year-old Julia Stiles plays video games at the Hugo Boss party.
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A 23-year-old Kerry Washington promotes Lift at Sundance.
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A 20-year-old Ryan Gosling poses for a snowy portrait ahead of the premiere of The Believer, three years before the release of The Notebook.
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Naomi Watts braves the cold in Park City. Just a few months later, she would break out in David Lynch’s Mulholland Drive.
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Tilda Swinton, all bundled up for the Sundance premiere of The Deep End.
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A 14-year-old Mischa Barton at Sundance for the premiere of Lost and Delirious.
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Green Dragon co-stars Patrick Swayze and Forest Whitaker at Sundance for their new film’s premiere.
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Mariah Carey goes all cowgirl while in Park City for the premiere of WiseGirls.
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A young Matthew McConaughey bundles up for Sundance.
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A supremely casual Ben Affleck—hoodie, beanie, wired headphones, and all—at the premiere of Gus Van Sant’s Gerry.
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2002
Christina Ricci and James Oliver share a moment at the Diesel party; the then-couple starred in the film Miranda.
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A radiant, 22-year-old Rosario Dawson in Sundance for the premiere of Love in the Time of Money.
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A 19-year-old Kieran Culkin at Sundance for the premiere of The Dangerous Lives of Altar Boys.
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2002
A cozy and plaited Patricia Arquette, posing for a portrait to promote the Charlie Kaufman film Human Nature.
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2002
A beanie-headed Robin Williams fools around at the 2002 edition while promoting his film One Hour Photo. He would proudly report overhearing viewers say that they forgot it was him in the lead role 15 minutes into the film.
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2002
Kyle MacLachlan took a break from promoting his film Miranda to play in the snow with a puppy, of course.
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2002
The Dangerous Lives of Altar Boys co-stars Jodie Foster and Jena Malone show the camera what they’ve got.
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Two years into their marriage, Brad Pitt and Jennifer Aniston attend the festival for the premiere of the latter’s latest drama, The Good Girl, alongside Sundance founder Robert Redford.
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2002
Hysterical Blindness’s Juliette Lewis gives a penetrating stare from within the pine trees.
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2002
Russell Crowe and Nicole Kidman pose before a screening of Kidman’s Birthday Girl. She kept the baker boy hat on all night, it seems from pictures.
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A fresh-faced Parker Posey attends the festival to promote Personal Velocity: Three Portraits.
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2003
The blueprint for Timothée Chalamet’s best bit of method-dressing during his A Complete Unknown press tour: a beanie-headed, plaid scarf-wearing Bob Dylan at the 2003 Sundance Film Festival for Masked and Anonymous.
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A young Renée Zellweger poses in Park City.
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Ben Affleck and Jennifer Lopez at the 2003 edition. Their wedding had previously been scheduled for the weekend of the festival, but was postponed and then called off—for a few decades, anyway.
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Penélope Cruz, bringing a little European sophistication to the festival while promoting Masked and Anonymous.
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Chloë Sevigny, in head-to-toe black, naturally, stops to pose on Park City’s Main Street.
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A year after Frida, Salma Hayek promotes her directorial debut, The Maldonado Miracle, at Sundance.
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A young Ryan Reynolds and Keri Russell kick back at the festival.
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Ahead of the premiere of her latest movie, The Singing Detective, a 24-year-old Katie Holmes consults the Sundance program.
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A 13-year-old Kristen Stewart promoting Jessica Sharzer’s teen drama Speak at Sundance.
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The Jacket co-stars Adrien Brody and Keira Knightley embody mid-aughts style while promoting their latest release.
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A year before he became James Bond, Daniel Craig attends a photo call for Layer Cake at Sundance.
