1980s
In August 1980, Waits married Kathleen Brennan, a screenwriter, whom he had met while working on the set of the Francis Ford Coppola movie One from the Heart. Brennan is regularly credited as co-author of many songs in his later albums, and Waits often cites her as a major influence on his work. She introduced him to the music of Captain Beefheart. Despite having shared a manager with Beefheart in the 1970s, Waits says, "I became more acquainted with him when I got married." Waits would later describe his relationship with Brennan as a paradigm shift in his musical development. After leaving Asylum, the label released the first Tom Waits "Best of" album in 1981, a collection called Bounced Checks, notable for including an alternate, stripped down version of "Jersey Girl" and the otherwise unreleased "Mr. Henry", as well as an alternate master of "Whistlin' Past the Graveyard" and a live performance of "The Piano Has Been Drinking". During this period, Waits appeared in a series of minor movie roles, including a cameo role in Wolfen (1981) as an inebriated piano player, and his song "Jitterbug Boy" also appeared on the movie's soundtrack. One from the Heart received its official theatrical release in 1982, with Waits appearing in a cameo as a trumpet player as well as receiving an Oscar nomination for Original Song Score (eventually losing out to Victor Victoria, by Henry Mancini and Leslie Bricusse). This marked the first in a series of collaborations between Waits and Coppola, with Waits appearing in cameos in Coppola's movies The Outsiders (1983), Rumble Fish (1983), and The Cotton Club (1984), and a major role in Bram Stoker's Dracula. Waits also contributed two songs to the documentary Streetwise (1984), "Rat's Theme" and "Take Care of All My Children".
After leaving Asylum for Island Records, Waits released Swordfishtrombones in 1983, a record that marked a sharp turn in his musical direction. While Waits had before played either piano or guitar, he now gravitated towards less common instruments, saying, "Your hands are like dogs, going to the same places they've been. You have to be careful when playing is no longer in the mind but in the fingers, going to happy places. You have to break them of their habits or you don't explore; you only play what is confident and pleasing. I'm learning to break those habits by playing instruments I know absolutely nothing about, like a bassoon or a waterphone." Swordfishtrombones also introduced instruments such as bagpipes ("Town with No Cheer") and marimba ("Shore Leave") to Waits' repertoire, as well as pump organs, percussion (sometimes reminiscent of the music of Harry Partch), horn sections (often featuring Ralph Carney playing in the style of brass bands or soul music), experimental guitar, and obsolete instruments (many of Waits' albums have featured a damaged, unpredictable Chamberlin, and more recent albums have included the little-used Stroh violin).
His songwriting shifted as well, moving away from the traditional piano-and-strings ballad sound of his 1970s output towards a number of styles largely ignored in pop music, including primal blues, cabaret stylings, rumbas, theatrical approaches in the style of Kurt Weill, tango music, early country music and European folk music as well as the Tin Pan Alley-era songs that influenced his early output. He also recorded a spoken word piece, "Frank's Wild Years", influenced by Ken Nordine's "word jazz" records of the 1950s. Apart from Captain Beefheart and some of Dr. John's early output, there was little precedent in popular music.
Waits's new emphasis on experimenting with various styles and instrumentation continued on 1985's Rain Dogs, a sprawling, 19-song collection which received glowing reviews (the album was ranked #21 on Rolling Stone's list of the 100 greatest albums of the 1980s. In 2003, the album was ranked number 397 on Rolling Stone magazine's list of the 500 greatest albums of all time.) Contributions from guitarists Marc Ribot, Robert Quine, and Keith Richards accompanied Waits' move away from piano-based songs, in juxtaposition with an increased emphasis on instruments such as marimba, accordion, double bass, trombone, and banjo. The album also spawned the 12" single "Downtown Train/Tango Till They're Sore/Jockey Full of Bourbon", with Jean Baptiste Mondino filming a promotional music video for "Downtown Train" (which would later become a hit for Rod Stewart), featuring a cameo from boxing legend Jake LaMotta. The album peaked at #188 on Billboard's Top 200 albums chart; however, its reputation has come to far outshine low initial sales.
Franks Wild Years, a musical play by Waits and Brennan, was staged as an Off-Broadway musical in 1986, directed by Gary Sinise, in a successful run at Chicago's famed Steppenwolf Theater. Waits himself played the lead role. Waits developed his acting career with several supporting roles and a lead role in Jim Jarmusch's Down by Law in 1986, which also featured two of Waits's songs from Rain Dogs in the soundtrack. In the same year, Waits also contributed vocals to the song "Harlem Shuffle" on The Rolling Stones' album Dirty Work.
In 1987, he released Franks Wild Years (subtitled "Un Operachi Romantico in Two Acts"), which included studio versions from Waits' play of the same name. Rolling Stone summed up the album's myriad styles this way: "Everything from sleazy strip-show blues to cheesy waltzes to supercilious lounge lizardry is given spare, jarring arrangements using various combinations of squawking horns, bashed drums, plucked banjo, snaky double bass, carnival organ and jaunty accordion." Waits also continued to further his acting career with a supporting role as Rudy the Kraut in Ironweed (an adaptation of William Kennedy's Pulitzer Prize-winning novel) alongside Jack Nicholson and Meryl Streep, in which Waits performed the song "Big Rock Candy Mountain", as well as a part in Robert Frank's Candy Mountain, in which Waits also performed "Once More Before I Go." In 1988, Waits performed in Big Time, a surreal concert movie and soundtrack which he cowrote with his wife.
In 1989, Waits appeared in his final theatrical stage role to date, appearing as Curly in Thomas Babe's Demon Wine, alongside Bill Pullman, Philip Baker Hall, Carol Kane, and Bud Cort. The play opened at the Los Angeles Theater Center in February 1989 to mixed reviews, although Waits' performance was singled out by a number of critics, including John C. Mahoney, who described it as "mesmerizing." Waits finished the decade with appearances in three movies: as the voice of a radio DJ in Jim Jarmusch's Mystery Train; as Kenny the Hitman in Robert Dornhelm's Cold Feet; and the lead role of Punch & Judy man Silva in Bearskin: An Urban Fairytale. His only musical output of the year consisted of contributing his cover of Phil Phillips' "Sea of Love" to the soundtrack of the Al Pacino movie of the same name and contributing vocals to The Replacements song "Date to Church", which appeared as a B-side to their single "I'll Be You".
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