TMS Muse of the Week: Winona Ryder

(Joe McNally)

Musician-actress Courtney Love once famously and crudely stated on VH1’s All Access: “You’re no one in rock music until if you’ve feuded with me or slept with Winona Ryder.” Depending on your familiarity with 1990s pop culture and celeb gossip, this could be an alarming claim. Most might know Courtney’s controversial reputation, but Winona’s maybe not as much. So many different things are associated with that unique namesake. Such as Winona’s preference for black clothes, dark make-up and her portrayal of the memorable character Lydia Deetz in Tim Burton’s Beetlejuice (1988) inspiring many goth girls in the ‘90s and early 2000s. Or her status as a Hollywood teen icon, picking up where Molly Ringwald left off, with movies like David Seltzer’s Lucas (1986), Michael Lehmann’s Heathers (1989) and Richard Benjamin’s Mermaids (1990). Winona was the face of Gen X for a bit when she starred in Ben Stiller’s indie romcom Reality Bites (1994); and she previously co-led the costume dramas of Francis Ford Coppola’s Dracula (1992), Martin Scorsese’s The Age of Innocence (1993) and Gillian Armstrong’s Little Women (1994) [the latter two earning her Oscar nominations for Best Supporting Actress and Best Actress]. If you’re part of Gen Z, you probably recognize Winona as Will Byers’ mom, Joyce on Netflix’s sci-fi ensemble series “Stranger Things” (2016- ); and unfortunately, you might have first heard of the movie star when she was bizarrely arrested for shoplifting a Saks Fifth Avenue store in 2001.

What Courtney—who’s actually a former friend of Winona—means by her comment is that the actress has a musically oriented taste in men. Behind her most famous relationship with fellow actor Johnny Depp from 1989 to 1992 [whom she co-starred with in Burton’s Edward Scissorhands (1990)], most of Winona’s boyfriends are actually music artists. You can spot her in the music video for Soul Asylum’s 1993 single ‘Without a Trace,’ back when she was living with frontman Dave Pirner. Four years later, Winona was unceremoniously dumped by Third Eye Blind’s Stephan Jenkins for model-actress Charlize Theron; and five years after that, she was rumored to be the inspiration for singer-songwriter Beck’s 2002 break-up album ‘Sea Change’ [though Beck himself later clarified the record was about a former non-famous girlfriend]. Flings with Pete Yorn, Conor Oberst of Bright Eyes and Rilo Kiley’s Blake Sennett followed near the end of Winona’s prime, and in between was a surprisingly lowkey relationship with Matt Damon. On top of all this, she also influenced a few songs as well, like indie music artist Matthew Sweet’s 1991 track ‘Winona’ and ‘Rollerskate Skinny’ by Old 97s, following a date between Winona and bandmate Rhett Miller in 2000.

(Atlantic Entertainment / Olive Films)

It seemed like the starlet was adored by nearly everyone at the end of the 20th century, but perhaps it’s not a huge shock hype that big would eventually implode. Ditching then BFF Gwyneth Paltrow for Courtney turned out to be a poor choice. Rumors of pill dependencies, bouts of depression and unreliable behavior on set; refusing to promote Janusz Kamiński’s Lost Souls (2000); four flops in a row, including an unlikely 2002 remake of Frank Capra’s Mr. Deeds Goes to Town (1936) co-starring Adam Sandler; and finally, a very publicized court case. People might not realize James Mangold’s Girl, Interrupted (1999) was originally intended to be a vehicle for Winona, before co-star Angelina Jolie quickly stole the film and won all the Best Supporting Actress awards as well. But, as history has proven, the public loves a comeback story, and Winona got her own after a break from the limelight; returning with supporting roles in popular projects like J.J. Abrams’ reboot of Star Trek (2009), Darren Aronofsky’s psychological dance piece Black Swan (2010) and “Stranger Things.” The former teen queen and her mentor, Tim Burton even reunited on a stop-motion remake of Tim’s Frankenweenie (2012) and for the music video of the Killers’ ‘Here with Me’ that same year.

One of my favorite Winona stories was when Laura Dern shared an amusing moment on Marc Maron’s podcast in 2013. Back in 1990, when the raven-haired star was 18, she once existentially exclaimed to Laura after her first visit to a psychiatrist about how it hit her she was one day going to be old enough to see her future son move out of the house. Three decades later, and Winona is ironically still childless and unmarried. Bachelorette, fashion icon, screen legend and minor criminal. Say what you will about Winona, you can’t accuse her of being forgettable.