1990s
The Black Rider: The Casting of the Magic Bullets—a theatrical collaboration of Waits, director Robert Wilson, and writer William S. Burroughs—premiered at Hamburg's Thalia Theatre on March 31, 1990. The project was based on a German folktale called Der Freischütz, with Wilson responsible for the design and direction, Burroughs for writing the book, and Waits for music and lyrics, which were heavily influenced by the works of Bertolt Brecht and Kurt Weill. In the same year, Waits contributed a cover of Cole Porter's "It's All Right with Me" to Red Hot + Blue, the first in the series of compilation albums from the Red Hot Organization — one of the first major AIDS benefits in the music business—which sold over a million copies worldwide. Jim Jarmusch directed a promotional music video for the song. Waits also collaborated with photographer Sylvia Plachy in the same year; her book Sylvia Plachy's Unguided Tour includes a short Waits record to accompany the photographs and text.
The following year, Waits was extremely busy working on movie soundtracks, acting, and contributing to a number of music projects by other artists. First, Waits appeared on the Primus album Sailing the Seas of Cheese as the voice of "Tommy the Cat", which exposed him to a new audience in alternative rock. This was the first of several collaborations between Waits and the group; Frontman Les Claypool would appear on several subsequent Waits releases. The same year saw Waits provide spoken word contributions to Devout Catalyst, an album by one of Waits' greatest influences, Ken Nordine, on the songs "A Thousand Bing Bangs" and "The Movie." Waits also contributed vocals to a duet with singer Bob Forrest on the song "Adios Lounge" on the Thelonious Monster album Beautiful Mess. He also contributed vocals to two songs ("Little Man" and "I'm Not Your Fool Anymore") on jazz tenor saxophonist Teddy Edwards' album Mississippi Lad. Edwards was extremely complimentary of Waits' contributions, saying:
Tom Waits is the one who got me my contract with PolyGram. He's wonderful, he's America's best lyricist since Johnny Mercer. He came down to the studio on the Mississippi Lad album, that's the first one I did for PolyGram, and he sang two of my songs, wouldn't accept any money, just trying to give me the best boost that he could.
The only collection of exclusively Waits-performed material of 1991 appeared when Waits composed and conducted the almost exclusively instrumental music for Jim Jarmusch's 1991 film Night on Earth, which was released as an album the following year. In July 1991, Screamin' Jay Hawkins released the album Black Music for White People, which features covers of two Waits compositions: "Heartattack & Vine" (which later that year was used in a European Levi's advertisement without Waits' permission, resulting in a lawsuit) and "Ice Cream Man". Waits continued to appear in movie acting roles, the most significant of which was his uncredited cameo as a disabled veteran in Terry Gilliam's The Fisher King. He also appeared alongside Kevin Bacon, John Malkovich, and Jamie Lee Curtis in Steve Rash's Queens Logic, and opposite Tom Berenger and Kathy Bates in Hector Babenco's film At Play in the Fields of the Lord, adapted from Peter Matthiessen's 1965 novel.
Bone Machine, Waits's first studio album in five years, was released in 1992. The stark record featured a great deal of percussion and guitar (with little piano or sax), marking another change in Waits' sound. Critic Steve Huey calls it "perhaps Tom Waits's most cohesive album... a morbid, sinister nightmare, one that applied the quirks of his experimental '80s classics to stunningly evocative—and often harrowing—effect... Waits' most affecting and powerful recording, even if it isn't his most accessible." Bone Machine was awarded a Grammy in the Best Alternative Album category. On December 19, 1992 Alice, Waits's second theatrical project with Robert Wilson, premiered at the Thalia Theatre in Hamburg. Paul Schmidt adapted the text from the works of Lewis Carroll (Alice's Adventures in Wonderland and Through the Looking-Glass, in particular), with songs by Waits and Kathleen Brennan presented as intersections with the text rather than as expansions of the story, as would be the case in conventional musical theater. These songs would be recorded by Waits as a studio album 10 years later on Alice. 1992 also saw Waits featuring in Francis Ford Coppola's film Bram Stoker's Dracula, as the possessed lunatic Renfield.
In 1993, he released The Black Rider, which contained studio versions of the songs that Waits had written for the musical of the same name three years previously, with the exceptions of "Chase the Clouds Away" and "In the Morning", which appeared in the theatrical production but not on the studio album. William S. Burroughs also guests on vocals on "'Tain't No Sin". In the same year, Waits lent his vocals to Gavin Bryars' 75-minute reworking of his 1971 classical music piece Jesus' Blood Never Failed Me Yet; appeared in Robert Altman's film version of Raymond Carver's stories Short Cuts and Jim Jarmusch's Coffee and Cigarettes: Somewhere in California, a short black-and-white movie with Iggy Pop; and his third child, Sullivan, was born. In 1997, Waits and Brennan wrote and performed the music for Bunny the animated short film by 20th Century Fox's Blue Sky Studios, which was awarded Best Animated Short Film by the Academy of Motion Picture Arts and Sciences.
In 1995, Holly Cole released Temptation, a tribute album consisting entirely of Waits covers.
Another Waits cover was released in 1996, as Meat Loaf covered Martha for his concept album Welcome to the Neighborhood.
In 1998, after Island Records released the compilation Beautiful Maladies: The Island Years, Waits left the label for Epitaph, whose president, Andy Kaulkin, said the label was "...blown away that Tom would even consider us. We are huge fans." Waits himself was full of praise for the label, saying "Epitaph is rare for being owned and operated by musicians. They have good taste and a load of enthusiasm, plus they're nice people. And they gave me a brand-new Cadillac, of course."
Waits's first album on his new label, Mule Variations, was issued in 1999. Billboard described the album as musically melding "backwoods blues, skewed gospel, and unruly art stomp into a sublime piece of junkyard sound sculpture." The album was Waits' first release to feature a turntablist. The album won a Grammy in 2000; as an indicator of how difficult it is to classify Waits's music, he was nominated simultaneously for Best Contemporary Folk Album (which he won) and Best Male Rock Vocal Performance (for the song "Hold On"), both different from the genre for which he won his previous Grammy. The album was also his highest-charting album in the U.S. to date, reaching #30.
The same year, Waits made a foray into producing music for other artists, teaming up with his old friend Chuck E. Weiss to coproduce (with his wife, Kathleen Brennan) Extremely Cool, as well as appearing on the record as a guest vocalist and guitarist. He also contributed a cover of Skip Spence's "Books of Moses" to More Oar: A Tribute to the Skip Spence Album, a collection of covers of the singer's songs on Birdman Records. The same year, Waits appeared in the comedy Mystery Men.
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