By the time Tom Waits released Franks Wild Years in August 1987, it had already been percolating for almost a decade.

In December 1978, fresh off of his experience playing the role of a pianist in Francis Ford Coppola's Paradise Alley, Waits set out to write a script of his own. Then called Why Is the Dream Always So Much Sweeter Than the Taste?, it was the tale of two old friends reuniting on New Year’s Eve. “It's a nice story. It's about a guy who's a success at being a failure and a guy who's a failure at being a success,” Waits later said, according to the Tom Waits Library.

The film never came to fruition, but it’s possible that seed of an idea that stuck with him as he turned his attentions back to his music and acting roles. By 1983, he had moved on from scriptwriter to playwright — at least he was headed in that direction.

That year, he released his seventh studio album, Swordfishtrombones, which is often considered the first installment of a trilogy. It included the song “Frank’s Wild Years," and follows a man named Frank, who presumably left his crazy past behind when he got married. He complains about trading them in for a mortgage, an unnamed wife who “mostly” keeps her mouth shut and a mangy Chihuahua named Carlos. In a surprise twist, he gets drunk one night and sets fire to the house with them both, presumably, inside. In an interview to promote the album, he noted it was inspired by the poet Charles Bukowski.

"Charles Bukowski had a story that essentially was saying that it's the little things that drive men mad,” Waits said. “It's not the big things. It's not World War II. It's the broken shoe lace when there is no time left that sends men completely out their minds. So this is kind of in that spirit. ... I think there is a little bit of Frank in everybody."

The following year, while writing the second album in the trilogy, Rain Dogs, Waits and his wife Kathleen Brennan, a screenwriter he met while working on Paradise Alley, also wrote the script for a play. It seemed to be a composite of Why Is the Dream Always So Much Sweeter Than the Taste? and "Frank’s Wild Years." Frank, whether the raging husband or the failed car salesman, or both, became Frank O’Brien, a poor, downhearted accordion player. He falls asleep on a bench and dreams of reunions and grandeur, before waking up reading to start anew. Early versions of the accompanying songs appeared on demo tapes in 1985, according to Barney Hoskyns, author of the 2009 Waits biography Lowside of the Road.

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The year prior, Waits had met Gary Sinise and Terry Kinney, co-founders of the Steppenwolf Theatre Company in Chicago, after a New York staging of Balm in Gilead, a play that had premiered at Steppenwolf using some of Waits' music in 1980. This laid the groundwork for the staging of his production of Franks Wild Years at Steppenwolf in 1986, with Sinise the theater’s artistic director and Kinney directing, though he eventually left duties to Sinise due to creative differences with Waits, according to the New York Times. Waits, of course, took on the lead role of Frank.

The Times also noted that the title character, played by Waits, seemed rather consistent with his stage persona — perhaps too much so. “All along, Mr. Waits has seemed to be playing the same part, so consistently one presumes the part is him.”

Bill Schimmel, who played accordion and keyboards in the pit, later said “Waits was inspirational throughout the rehearsals. When the band had worked up and taped an arrangement, [bassist and horn player] Greg Cohen would hand a cassette to Waits, who'd come in after rehearsing with the Steppenwolf actors,” he said. “Concerned that the music might stagnate through nightly repetition, Waits urged the musicians to make deliberate mistakes. He'd want more funny notes and he'd want tricky little train wrecks in the textures. If we were getting a little too tight, he would be a little bit wary about that. He always wanted a bit of a rub in everything, and when we got that right he seemed to be relatively satisfied."

The show enjoyed a two-month sold-out run at Steppenwolf, with mixed reviews. The New York Times said “It cannot be counted a complete success, but there are reasons for its problems, probably correctable ones.” His everyman characters could not overcome their inherent clichés, making it “decent, but conventional.”

The album of the same name (with the subtitle Un Operachi Romantico in Two Acts) was released on Island Records the following year, completing the trilogy. The songs, while less accessible than many of Waits' already offbeat albums, seemed to work, if it didn't quite connect the tell the plot line on its own. Fans largely considered it, and the style he had begun to adopt with Swordfishtrombones, a success. It only reached No. 115 on the Billlboard 200, but Waits was accustomed to being more of a cult star — more interested in how deeply he reached his fans than how many of them there were. While Waits had described the story as Eraserhead meets It's a Wonderful LifeRolling Stone wrote, "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."

Previously, Waits had played only guitar or keyboards, but with Franks Wild Years his instrumentation was becoming more atypical. "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," he later said of his experimentation. "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."

Nonetheless, Rolling Stone said "it's Waits's gravel-pit voice, from which he digs a number of distinct characterizations, that remains the most striking instrument."

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