All Access: Winona Rules

Premiered on VH1 in July 2003. On-camera interview and research source.

All Access: Winona Rules

Winona Ryder… movie star… serial rock star dater… convict – she’s Hollywood’s favourite enigma. All Access: Winona Rules! goes beyond the big brown eyes to reveal details about the life and times of the mysterious movie star.

This half-hour All Access show will include interviews with respected Winona biographer Nigel Goodall, Hollywood insiders, entertainnment journalists, friends of Winona, court reporters and, of course, the rock and rollers she can’t live without.


“You’re no one in music until you have feuded with me or until you sleep with Winona!” – Courtney Love.

  • Johnny Depp – dated three years. First clapped eyes on each other at the premiere of Great Balls of Fire. Engaged to be married Feb. 1990. He got a tattoo declaring Winona Forever. When they broke up in 1993, he had it changed to Wino Forever.
  • Two-week fling with Christian Slater after completing Heathers.
  • Matt Damon – introduced by Gwyneth Paltrow. Engaged, broke up.
  • Denied dating David Duchovny and Dodi Fayed.
  • Speculation: Brittany Murphy. Dated rockers Pete Yorn and Jay Kay.
  • Rumored: Daniel Day Lewis.
  • Also: Dave Grohl, Evan Dando, Beck, Ryan Adams.
  • Now linked to Jimmy Fallon.


Winona is the inspiration for at least 8 pop songs!

  • Winona – Matthew Sweet.
  • Rollerskate Skinny – Rhett Miller (Old 97s).
  • Winona – Drop Nineteens.
  • Holley Carbines – Winona Ryder.
  • The Kennedys – Why, Winona, Why?
  • Ridel High – (She Looks Like) Winona Ryder.


Winona gave her support to the family of abducted girl, Polly Klass.

  • Polly Klass was from Winona’s hometown.
  • Offered $200,000 for information on the abduction.
  • Dedicated “Little Women” to Polly.
  • Polly’s father, Marc Klaas has been a vocal supporter of Winona’s during her trial.


America’s Gen X poster girl has fallen from grace – gracefully! We’ll set this act up with her career highlights, and then shift to her wild ride into oblivion.


Winona was the focus of Hollywood’s biggest non-murder trial in years. Ever the good sport, she even made fun of herself on Saturday Night Live.

  • History of stealing? says she’s been nabbed before! Learn about the shoplifting skeletons in her closet!
  • December 12, 2001 – Winona busted at Saks in Beverly Hills for shoplifting, vandalism – for stealing $5,560.40 worth of merchandise.
  • Security video captured the whole mess!
  • Free Winona t-shirts become all the fashion.
  • Wacky, wild trial began Oct. 28, 2002.
  • Winona guilty. Sentenced to 3 years’ probation, $10K fines, 480 hours community service.
  • History repeating itself – Winona’s clepto past!
  • Ironic twist: One of the items Winona attempted to steal was a Marc Jacobs top. Jacobs would later use Ryder in an ad campaign.


With LSD guru Timothy Leary as a godfather, and counter-culture poet Allen Ginsberg as a close family friend, Winona was exposed to drugs at an early age. But could this doe-eyed damsel really be a pill-popper? Consider the facts:

  • When she was arrested on shoplifting charges, Winona was also carrying a syringe and several prescription drugs, including: 1 bottle of liquid Demerol, 1 bottle of Diazapam, 6 tablets of Valium, 40 tablets of Vicoprofen, 2 tablets of Vicodin, 1 capsule of Kadian, 2 tablets of Percocet, 1 tablet of Percodan.
  • A probation report made public revealed that between 1996 and 1998, Ryder had 20 doctors to write 37 prescriptions.


  • Checked herself into a hospital at age 20, after her role in The House of the Spirits for treatment for depression.
  • Plagued by bronchial and sinus infections since she was a child.
  • Dropped out of British indie Lilly And The Secret Planting due to stomach disorder.
  • Broke her arm during the filming of Mr. Deeds after falling off a bicycle.


  • Westerberg High, the setting of Heathers, was named after Paul Westerberg, singer of Winona’s favorite band, the Replacements.
  • Real name: Winona Laura Horowitz.
  • Winona is a natural blonde!
  • Winona’s favorite book: The Catcher in the Rye. She says she owns every hardback and paperback edition and every translation.
  • Winona collects vintage clothes, including a Sandra Dee bikini from the Tammy movies and an Ava Gardner dress she wore to the 2000 Oscars.
  • Missed opportunity: Cast as Mary Corleone in The Godfather Part III, but dropped out due to illness.
  • Gwyneth Paltrow scoped out the script for Shakespeare in Love on Winona’s coffee table. Gwyneth won the Oscar, but lost a friend.