Lowside of the Road: A Life of Tom Waits

by Barney Hoskyns

As vital as this early immersion in black music was, it was offset by the influence of rock’s first great poet. Bob Dylan’s dense lyrics were a gateway for any aspiring singer-songwriter growing up in the early 1960s folk era, and Waits got the Dylan bug bad, plastering his bedroom walls with transcriptions of his songs. The complex chains of images in such masterpieces as Highway 61 Revisited’s epic “Desolation Row” would influence Waits for years to come. As seminal as seeing James Brown in Balboa Park was the Dylan show Waits saw two years later, on 4 December 1964. Held in the Peterson Gymnasium at San Diego State University, the concert set Waits reeling. “Here’s a guy like Dylan on stage with a stool and a glass of water, and he comes out and tells these great stories in his songs,” he recalled of the gig. “It helped unlock the mystery of performance.” Four years away from writing his first song, the fifteen-year-old Waits was

“Teachers and ministers. I wanted to break windows, smoke cigars and stay up late, you know?” Dragged along to the Friends Church every Sunday by Alma, Waits yearned to break out of Chula Vista. “I wore a tie that cut off the circulation to my head,” he later recalled.“Then I discovered donuts, cigarettes and coffee when I was fourteen, and that was it for church. My mom said, ‘Don’t forget there’s nothing the devil hates more than a singing Christian.’”

It was Kerouac’s America – a cityscape of displaced, marginalized street people – that hooked the teenage Waits as he scrubbed the cutlery at Napoleone’s.

“I enjoy [Kerouac’s] impressions of America, certainly more than anything you’d find in Reader’s Digest,” he recalled. “The roar of the crowd in a bar after work; working for the railroad; living in cheap hotels; jazz.” Kerouac was Waits’ passport to the after-hours world, a place where a young nighthawk could pick up scraps of conversation and use them to piece together the lives of anonymous uncelebrated Americans.

More than anything, the job afforded Waits countless opportunities to gather scraps of conversation he heard from passers-by on the street. “I’d bring my books and my coffee and my cigarettes and put my feet up,” he remembered. “And I’d read my Kerouac and watch the cars go by, and I just felt like I was on fire and I had a reason to live. Sitting there, my own ordinary life was just lifted out of that and I was all dusted with something sparkling.”

Waits’ first great song, “Ol’ ’55” came out of the first flush of love rather than from its dissolution. A mumbly, countryish paean to his beat-up old Buick, it painted a vivid picture of a young man rising reluctantly from his girlfriend’s bed at dawn to drive home on the freeway. He was pining for his girl, and the cars were flashing him to get out of the fast lane, but he felt “so holy” and “so alive” as the stars faded and the sun rose on the horizon. Historian Simon Schama would describe it as “the single most beautiful love song since Gershwin and Cole Porter shut their piano lids”.

The sleepy and fairly ordinary “Midnight Lullaby” was an early instance of Waits borrowing from nursery rhymes and lullabies, in this case “Sing a Song of Sixpence” and “Hush Little Baby”. Thus began a lifelong habit of assembling lyrics from fragments of oral tradition.

one fondness I have for Closing Time is that it is that early Tom.”

Exactly who was going to fall for this hobo romantic with his heart in the past?

“We struck on Kerouac’s concept of wanting to be at ‘the center of Saturday night in America,’” Bob Webb recalls. “We got caught up in that literary notion and decided that each of us would create something around the theme. I drove home and stayed up all night writing

Waits – in “$2.50 used imitation alligator boots” – sauntered off into the night, taking Wiseman to a tired diner on Sunset called the Copper Skillet. Here, in the wee small hours, he reiterated his commitment to the nocturnal life, saying he’d always be a “night owl” and would never move to a cabin in Colorado. “The moon beats the hell out of the sun,” Waits said. “There’s something illusionary about the night … your imagination is working overtime … there’s food for thought at our fingertips and it begs to be dealt with.” Wiseman finally departed at 6.10 a.m., leaving Waits to catch a few hours’ sleep at the Tropicana – even though “he’s kept his one-bedroom house” – before leaving to play two nights at the University of Minnesota.

At night Jones would swim in the Tropicana pool. “I’d […] look up at the moon and imagine, ‘So this is what it’s like to be a movie star, to own the moon and the palms and the night air, to be beautiful and have the whole history of your life still approaching,’”

Like the protagonist of Jimmy Webb’s “By the Time I Get to Phoenix” – and almost like a reverse version of the callow youth in “Ol’ ’55” – the Waits of “Ruby’s Arms” stole out into the dawn, grabbing only his jacket and boots (and “the scarf off of your clothesline”) as he left forever.

Asked to explain the album’s eventual title, Waits said that Rain Dogs were “people who sleep in doorways … people who don’t have credit cards […] who don’t go to church […] who don’t have, you know, a mortgage … who fly in this whole plane by the seat of their pants”. Later he classified such characters as “hobos, prostitutes, people in trouble … the negative machinery I create to motivate myself”.¶

He could do the Rasputin thing. Tom could make himself invisible, and that blew me away.” For Schimmel it was part of the mystery of Waits that he could somehow act his way into not being Tom Waits.

Schimmel also witnessed Waits unwind after his performances as Frank.“He would sometimes drive me home from the theater in the Citation,” Bill recalls. “And in the car he would start to free-associate. He was coming down after the performance, and he would start to free-associate poetically. I really enjoyed that.”