David Bowie’s career spanned six decades, and as such, fans of varying ages have different memories. For those of us who suffered diligently through the eighties and nineties, these five cultural touchpoints might ring a bell. Leave your own recollections in the comments…

5. Bowie and Bing, 1977

This rendition of Little Drummer Boy, originally recorded for a 1977 TV special: Bing Crosby’s Merrie Olde Christmas, became a radio standard in the eighties — adding to the long list of ridiculous things we took seriously. But heck, it’s a nice arrangement… Bowie wrote the Peace on Earth harmony, and the duo recorded just a month before Bing Crosby died, marking one of his final recordings.

4. Cool World, 1992

Cool World is half live-action, half animation and stars Kim Basinger, Gabriel Byrne, and this young up-and-comer named W. Bradley Pitt. It ranked among my very favorite films in 1992, because I was 14, and it was on a relatively short list of PG-13 films I’d ever been allowed to see. So of course I remember it as an edgy, avant-garde masterpiece… In reality notsomuch, but its soundtrack was kick-ass and got (much) better reviews than the film, featuring a song written by Bowie and produced by Nile Rodgers  — Real Cool World — as well as tracks by the Thompson Twins, Ministry, and Moby. The video is quite the slice of the early nineties, too: we never actually see Bowie’s face, but his dance moves rival Christopher Walken’s.

3. The Breakfast Club, 1985

We all know how the movie starts… the lyric from Changes appears on a black title screen. We read it solemnly, knowingly, even though we’re confused as hell. Then the screen shatters, and we’re left with the exterior view of Shermer High School on a gray morning. There’s really not much more to the Bowie Lyric Legend of The Breakfast Club (that I can find), except that Ally Sheedy might have suggested it. Regardless, there it will always be, perplexing viewers until the end of time.

2. The Man Who Sold the World – Nirvana cover, 1993

Fast-forward to 1993, when the thrift store sweaters and plaid flannels started to emerge, along with the fast-and-furious trading of Nirvana albums bootlegged onto Maxell blank cassette tapes. The one that required two blank tapes was Nirvana Unplugged, which included the cover of Bowie’s The Man Who Sold the World that grungy teenagers everywhere proclaimed ‘the best Nirvana song ever.’ Such wankers, we were.

1. Labyrinth, 1986

Bowie as The Goblin King Jareth was probably the only reason my older brother would ever deign to watch a movie with me in the eighties, but I didn’t care — there he was, pretending not to enjoy one of Bowie’s five original tunes on the soundtrack. Like most of the films from my youth, this one received tepid reviews, but has since become a cult classic. On a side note, I’m really hoping to see a lot of Jareths this Halloween.