Hermit Bob, the woods-dwelling recluse in director Jim Jarmusch’s celeb-studded new zombie film, The Dead Don’t Die, is like a character in a Tom Waits song. He lives on the fringes of civilization. He has a vast, Hagrid-like beard. He mutters to himself as he watches zombies attack people in his small Midwestern town. It’s easy to imagine Hermit Bob commiserating with equally unsavory characters from Waits’ songbook, like Dave the Butcher and Table Top Joe.

So it’s fitting that Jarmusch gave the role to Waits himself. The celebrated independent filmmaker famously loves to cast musicians in his films—The Dead Don’t Die also includes Iggy Pop, Selena Gomez, and RZA in its ensemble cast—but he has a special working relationship with Waits dating back 33 years. As Barney Hoskyns writes in his Waits biography Lowside of the Road, Jarmusch and the musician met in the early 1980s at a party hosted by Jean-Michel Basquiat. Both men felt awkward and shy among glamorous art people, so they ditched the party and went on a bar crawl instead.

They became fast friends, sharing a similar bent sensibility. “Tom and I have a kindred aesthetic,” Jarmusch told Hoskyns. “An interest in unambitious people, marginal people.” Plus, they both looked astoundingly fly in a decade in which most famous men looked like unwashed poodles. Just look at this vintage shot of the pair sitting on a park bench in 1985.

By the mid ’80s, both Jarmusch and Waits were enjoying major breakthroughs: the former with Stranger Than Paradise, a career-making indie hit; the latter with Swordfishtrombones, which had Waits trading in his piano crooner roots for a gruff, clanging new sound. The filmmaker promptly recognized Waits’ acting ability—his raspy voice, his knack for portraying devilish outsiders and absolute weirdos—and cast him in 1986’s Down by Law. Waits has enjoyed a Hollywood side-hustle ever since, cropping up in films as varied as Bram Stoker’s Dracula, Seven Psychopaths, and the Coen brothers’ recent The Ballad of Buster Scruggs. Jarmusch, though, knows how to bring out the best in Waits the character actor, having worked with the reclusive singer more than any other filmmaker. Here’s a guide to the wonderful and strange ways Jarmusch has included Waits in his films.

Down by Law (1986)

After taking odd parts in a string of films directed by Francis Ford Coppola, Waits got his first shot at a leading role in Down by Law, Jarmusch’s gritty and endearing fable about three cellmates who break out of jail and prowl the Louisiana bayou together. Waits, looking impossibly young and handsome at 36, plays Zack, a sullen, down-on-his-luck disc jockey who’s been framed for murder. The joy of this movie is watching Waits’ character interact with his fellow escapees, a pimp (John Lurie) and an upbeat Italian guy who never shuts up (Roberto Benigni); Robby Müller’s acclaimed cinematography frequently captures all three men in the same shot, bickering about the inanities of life.