Entertainment
Winona Ryder’s Must-See Throwback Photos
Winona Ryder has been a Hollywood darling for decades!
Studying acting at San Francisco’s American Conservatory Theatre, Ryder landed her on-screen debut at age 14 in 1985’s Lucas and then became a household name — thanks to standout performances in films like Beetlejuice (1988), Heathers (1988), Edward Scissorhands (1990), Mermaids (1990) and more. Off-screen, her personal life also captivated the public, from high-profile romances with Johnny Depp and Matt Damon to her infamous shoplifting scandal in 2001.
While she stayed active in the 2000s, her career rose again in 2016 with her Golden Globe-nominated role on Netflix’s Stranger Things. From there, she made notable appearances in projects such as The Plot Against America (2020) miniseries, Haunted Mansion (2023) and the Beetlejuice Beetlejuice (2024) sequel.
As the actress has continued to make headlines and grace the screen, it’s a great time to look back at her early days in the limelight. Scroll below to see the best throwback photos of Ryder from the 1980s to the early 2000s.
Bright-Eyed Ambition
The iconic brunette sported lighter locks as a teen in the mid-’80s.
Golden Girl
Ryder posed with her Square Dance costar Rob Lowe at the 1988 Golden Globes.
Good to be Bad
In 1989, the then-17-year-old actress smiled on the Academy Awards red carpet alongside her Heathers castmate, Christian Slater.
White Hot
The actress chose an all-white outfit for the 1989 premiere of Great Balls of Fire, where she met her soon-to-be-boyfriend, Depp.
Star Power
Ryder scored her first-ever Golden Globe nomination for 1990’s Mermaids, costarring Cher and Christina Ricci.
Making the Cut
The Edward Scissorhands star laughed it up with director Tim Burton, costar/then-boyfriend Depp and composer Danny Elfman at the film’s 1990 premiere.
Got the Spirit
A feisty Ryder, here in 1990, got goofy after landing in Los Angeles.
Award-Worthy
Former couple Depp and Ryder kept it dark and mysterious at the 1991 Golden Globes.
Bite Out of Life
Ryder sported a romantic look at the 1992 premiere of Bram Stroker’s Dracula, which also starred Sadie Frost and Gary Oldman.
Friends Forever
One of Ryder’s oldest and dearest Hollywood friendships is with Keanu Reeves, with whom she’s remained close since they met in the late ’80s. They’ve costarred together in Dracula, A Scanner Darkly (2006), The Private Lives of Pippa Lee (2009) and Destination Wedding (2018).
Classically Cute
The actress shined on the 1996 Oscars red carpet.
Best Buds
Ryder and fellow ’90s queen Claire Danes became friends after working together on 1994’s Little Women. They proved their bestie status with matching red lips at the 1996 Fire & Ice Ball in Burbank, Calif.
Hug It Out
Courtney Love embraced the actress at a cocktail party in 2001.
Date Night
Ryder attended the 2000 Globes with then-boyfriend Damon, whom she met through friend Gwyneth Paltrow.
Back to Reality
Ryder congratulated her former Reality Bites costar, Ethan Hawke, at the 2004 premiere of his movie Before Sunset.
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