Winona Ryder's Best Throwback Photos

Ron Galella Archive - File Photos 2011 — Winona Ryder attends the N.Y.C. premiere of 'Great Balls of Fire' on June 26, 1989. Photo:
Ron Galella/Ron Galella Collection via Getty Images

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.

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Bright-Eyed Ambition

Winona Ryder poses for a portrait circa 1985. Time Life Pictures/DMI/The LIFE Picture Collection/Getty

The iconic brunette sported lighter locks as a teen in the mid-'80s.

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Golden Girl

Ryder posed with her Square Dance costar Rob Lowe at the 1988 Golden Globes.

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Good to be Bad

61st Annual Academy Awards - Arrivals — Winona Ryder and Christian Slater attend the 61st annual Academy Awards on March 29, 1989. Ron Galella/WireImage

In 1989, the then-17-year-old actress smiled on the Academy Awards red carpet alongside her Heathers castmate, Christian Slater.

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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.

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Star Power

Winona Ryder And Cher In 'Mermaids' — From left: Winona Ryder, Cher and Christina Ricci in 'Mermaids,' in 1990. Metro-Goldwyn-Mayer/Getty

Ryder scored her first-ever Golden Globe nomination for 1990's Mermaids, costarring Cher and Christina Ricci.

06 of 15

Making the Cut

"Edward Scissorhands" Premiere — From left: Tim Burton, Winona Ryder, Johnny Depp and Danny Elfman attend the premiere of 'Edward Scissorhands' on Dec. 6, 1990. Barry King/WireImage

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.

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Got the Spirit

A feisty Ryder, here in 1990, got goofy after landing in Los Angeles.

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Award-Worthy

Johnny Depp and Winona Ryder attend the 48th annual Golden Globe Awards on Jan. 19, 1991. Ron Galella/Wireimage

Former couple Depp and Ryder kept it dark and mysterious at the 1991 Golden Globes.

09 of 15

Bite Out of Life

"Dracula" Hollywood Premiere — From left: Sadie Frost, Winona Ryder and Gary Oldman attend the premiere of 'Bram Stroker's Dracula' on Nov. 10, 1992. Ron Galella, Ltd./WireImage

Ryder sported a romantic look at the 1992 premiere of Bram Stroker's Dracula, which also starred Sadie Frost and Gary Oldman.

10 of 15

Friends Forever

Winona Ryder and Keanu Reeves attend the fourth annual Independent Spirit Awards on March 25, 1989. Ron Galella Collection via Getty

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).

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Classically Cute

The 68th Annual Academy Awards — Winona Ryder attends the 68th annual Academy Awards on March 25, 1996. Jim Smeal/WireImage

The actress shined on the 1996 Oscars red carpet.

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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.

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