After stealing a handful of rock stars from their long-term paramours (Remember Soul Asylum‘s Dave Pirner? Neither do we), Winona Ryder revealed that she also had a penchant for stealing high-end couture, after getting busted for shoplifting at a Beverly Hills Saks in December 2001. Surveillance cameras caught the then-30-year-old star acting about half her age, as she tried to slip out of the store with more than $6,000 worth of merchandise.
The cherry on top of this mess: painkillers were found in Winona’s purse. A prescription for them was not. Suddenly, her brief but very public association with Courtney Love around that time made a lot more sense. Winona subsequently treated her arrest as, like, no big deal. She poked fun at the whole episode during a bizarre stint as the host of Saturday Night Live (“I love free stuff!”), and appeared on the cover of W magazine wearing one of those “Free Winona” t-shirts. Kids, they never learn.