Actress Winona Ryder burst onto the scene in the 1980s and quickly made a name for herself with quirky, alternative film roles. As her star continued to rise in the 90’s, she became nearly as well-known for her relationships with other celebrities—musicians, in particular— as for her acting skills. Some of her famous paramours wrote songs for her, while other musicians were inspired by their crushes on the actress. The trend of “songs about Winona” reached its fever pitch when Ryan Adams’ 2001 album Gold was rumored to be almost entirely about his passionate affair with the actress. He later explained that he had never dated Winona at all.
Matthew Sweet released the song “Winona” on his third album, Girlfriend, in 1991. He later confessed that he’d named it after Winona Ryder, although the two never dated.
After her high-profile relationship with fellow actor Johnny Depp, Winona dated Soul Asylum lead singer Dave Pimer. The band’s song “Just Like Anyone” is said to have been written about Winona, although the video features Claire Danes.
Old 97’s lead singer Rhett Miller claims to have written their song “Rollerskate Skinny” after his first date with Winona. The song’s title is a reference to The Catcher in the Rye, one of her favorite books.
Beck dated Winona briefly in 2000, then wrote several songs about her that appear on his Sea Change album. “Lost Cause” is just one of the many sad songs from this classic album.