Tom Waits has had a highly successful music career for half a century and became the voice of a generation who’d never heard of him. For those who have, he’s arguably the greatest songwriter who’s ever lived, and for the uninitiated, he’s the guy who wrote Downtown Train for Rod Stewart. Also, the musician starred in almost 50 movies; most of them are small roles, but even Waits’ few lines of dialogue can be a highlight of a film.

Waits has worked with iconic filmmakers, including directors Jim Jarmusch, Francis Ford Coppola, and Terry Gilliam. Often, he’ll play some variation of himself (or the legendary, gruff-voiced everyman persona he’s cultivated over the years), but there are some unexpected performances as well; case in point, for Gilliam’s The Imaginarium of Doctor Parnassus, Tom Waits played the devil and does a wicked good job.

The musician always brings to a special atmosphere to films, but Waits admits acting doesn’t come naturally to him. “It’s a lot of work to try and be natural, like trying to catch a bullet in your teeth,” he told Rolling Stone. Let’s look at the best Tom Waits performances, movies in which he caught the bullet.

8 Short Cuts

     Spelling Television

The 1993 comedy-drama Short Cuts tells the extraordinary story of 22 characters’ ordinary days. Each of them live in the suburbs surrounding Los Angeles and have their own problems. The New York Times proclaimed, “When future social historians want to know what the temper of life was like in one corner of America in 1993, Short Cuts will be a motherload of information.” Tom Waits plays a limousine chauffeur who drinks too much. The great ensemble cast of Short Cuts, including Tom Waits alongside Julianne Moore, Robert Downey Jr., Tim Robbins, Jack Lemmon, and countless others, won a Golden Globe Special Award for Ensemble and Venice Film Festival Special Volpi Cup.

7 Bram Stoker’s Dracula

     American Zoetrope

In 1992, Francis Ford Coppola made one of the best adaptation of Bram Stoker’s novel, focusing on a uniquely gothic blend of romance and horror. Featuring an impressive A-list cast including Gary Oldman, Winona Ryder, Keanu Reeves, and Anthony Hopkins, Bram Stoker’s Dracula captured the gothic, creepy, and beautiful spirit of the vampire story. Tom Waits (who had previously scored Coppola’s film One From the Heart) portrays Renfield, Dracula’s mad servant who likes to eat bugs. Waits gives a charismatic performance here, sinister and comedic at the same time.

6 Seven Psychopaths

     Blueprint Pictures

The 2012 entertaining dark comedy Seven Psychopaths follows a writer (in one of the best Colin Farrell performances) who, working on his crime screenplay of the same name as the film, finds that he is surrounded of psychopaths when his friend nabs a violent maniac’s dog. In the film Tom Waits portrays one of the seven psychopaths, Zachariah. It is interesting that Waits agreed to the role without reading the script; the fact that his character would be surrounded by rabbits was enough for him.

5 The Old Man & the Gun

     Identity Films

The Old Man & the Gun is an unexpectedly touching 2008 crime film about the last years of Forrest Tucker (played by Robert Redford), a bank robber who escaped from prison 18 times. For sure, the main star of The Old Man & the Gun is Robert Redford, a movie legend who says that this film will be his last, and other legendary actors like Sissy Spacek and Danny Glover also shine. But Tom Waits’ performance is also stunning, appearing as Tucker’s sidekick Waller. His monologue about hating Christmas is arguably the best bit of dialogue in The Old Man & the Gun.

4 Rumble Fish

One of the best Francis Ford Coppola movies, the 1983 drama Rumble Fish tells the story of two brothers, a younger one (played by Matt Dillon) wants to be as good as his older brother, a gang leader (played by Mickey Rourke). This film is offbeat, experimental, and breathtaking, remaining an underrated masterpiece overshadowed by Coppola’s ’70s films. In Rumble Fish, Tom Waits steps into the role of Benny, barkeeper who’s always ready to give philosophical advice. Waits got a chance to pick out his own costume and write his own dialogue. The most powerful scene with Waits in the movie involves a clock, which is accompanied by a poetic monologue about time.

3 Licorice Pizza

     Metro-Goldwyn-Mayer

Paul Thomas Anderson’s Licorice Pizza is a warm, nostalgic, and joyful love letter to the 1970s. This coming-of-age comedy-drama centers on the love story of teenage actor Gary (a winning debut performance from Cooper Hoffman) and photographer’s assistant Alana (Alana Haim’s film debut too). Tom Waits appears as film director Rex Blau, who isn’t afraid to be loud. As always, Waits is the scene-stealer. Alana Haim opened up to NME about the scene with Tom Waits, saying: “He had the best vibe. When he came to set it was hard because I’m a sandwich between Sean Penn and Tom Waits, and it’s like: “Who do you focus on?!” It was a crazy sandwich to be in.”

2 Coffee and Cigarettes

     Cinesthesia Productions

Jim Jarmusch’s remarkable anthology Coffee and Cigarettes contains 11 black-and-white short films in which great actors and musicians have conversation over coffee and cigarettes. The segment with Tom Waits and Iggy Pop, Somewhere in California, won the highest prize given to a short film at the 1993 Cannes Film Festival. Waits and Pop play themselves, two musicians in a coffee shop. They have quit smoking and decide that now they can celebrate this achievement with one more cigarette. It is impossible to resist being drawn into their dialogue, as simple as it is genius. Coffee and Cigarettes proves that sometimes interesting conversations are all we need in a movie.

1 Down by Law

     Black Snake

Down by Law is an ’80s cult classic written and directed by Jim Jarmusch. This 1986 black-and-white film follows three men (a disc jockey, a pimp, and an Italian tourist) who escape from jail. Their funny and occasionally sad journey is highly worth watching, and cemented Jarmusch’s status as one of the great American independent filmmakers. Three main actors (Tom Waits, John Lurie, and Roberto Benigni) give extraordinary performances. Waits is outstanding as an out-of-work disc jockey with a mocking smile and a grumpy mood, and his own music accompanies parts of the film perfectly. This is the first leading role in Waits’ on-screen career, and he handled it brilliantly.