Tom Waits - Live at the Detroit Opera House, Aug. 11, 2006

By Land, Sea, and Air

Deployment, 2006. Picture this: I’m adrift somewhere in the sweltering brine of the South China Sea, perched on the bowels of the USS Enterprise, the first nuclear-powered aircraft carrier—a floating fortress with all the charm of a strip mall designed by Kafka.

And then — ka-boom — Tom Waits drops his Orphans tour dates. Nine shows in thirteen days. A celestial event for the faithful, the kind of thing that happens when stars align or when Tom gets tired of tinkering with broken calliopes in the backwoods of Sonoma. One of those dates? August 11, Detroit Opera House. My hometown. The city of burning steel and broken dreams.

Now, Tom Waits doesn’t tour. He doesn’t need to. Touring for him is like asking Bukowski to run a PTA meeting. Back in the ‘70s, he endured opening slots for bands whose fans couldn’t fathom his whiskey-lacquered growls and smoke-choked ballads. They jeered, and he swore off the road like it was a busted Dodge Dart. Marriage, sobriety, and a newfound love for doing whatever the hell he pleased only deepened the rift. Tom Waits touring is a cosmic fluke, like finding a mint-condition Velvet Underground acetate in your uncle’s garage.

So, naturally, I lost my mind. I had orders to transfer mid-deployment, moving from Norfolk to San Diego. But forget logistics—this was about Tom Freaking Waits. I fired off an email to my ride-or-die, Matt, breaking every operational security rule in the book. Matt understood the mission. Less than twelve hours later, my man had secured the grail: two physical tickets for Tom Waits in Detroit. Game on.

By August 8, I was breaking free of the Enterprise under a smog-choked Singapore sky, the ship fading into the murk like a bad memory. A hellish chain of flights followed—Singapore to Tokyo, Tokyo to SeaTac, SeaTac to Dulles, Dulles to Norfolk. Every airline attendant seemed hellbent on turning us into the drunkest sailors ever to stagger off a plane. Liquor bottles rained down like confetti. By the time I hit my Graydon Avenue crash pad, I was half-dead, running on fumes and duty-free scotch.

The next day, movers swept through like locusts, leaving me with two bags of clothes, my uniforms, and an overstuffed CD case. I pointed the nose of my ‘96 Ford Escort toward Pittsburgh, the plan as clear as Tom Waits’ gravel-coated voice: grab Matt, drive to Michigan, and bask in the glow of weird brilliance.

Matt, the sorcerer, had already pulled off another miracle—quitting his job but somehow wrangling a week’s pay and two vacations out of it. He was ready to ride shotgun, wallet fat from Navy travel reimbursements, as we careened through the Midwest with Primanti Brothers sandwiches and coffee fueling our trek. That Escort? A steel pony of pure endurance, squeezing 48 miles per gallon out of its four-cylinder heart. It was the road trip equivalent of Rain Dogs—all guts, no glamour.

Didn’t know Detroit could look like this, didja?

We hit Michigan like a fever dream, crashing at my dad’s place before heading to the Opera House. Detroit shimmered in the August heat, gritty and glorious, like it always does. Tom Waits took the stage like some shamanic drifter, no preamble, no opening act —just him. He didn’t just sing. He became his characters, every growl and rasp a portal into the weird, wild underbelly of Americana. It was vaudeville, carnival, jazz, and blues rolled into one beautifully broken package.

Matt and I left the show buzzing, drunk on the kind of performance you carry with you like a scar. To this day, we’re the only people we know who’ve seen Tom Waits live. And maybe that’s how it should be — a secret handshake with the universe, a night when everything else faded, and the music stood eternal.

We made Indianapolis the following night, after deep dish with Dad at the now-defunct Original Cottage Inn in Ann Arbor (RIP, you beautiful mess). After Indy, we blasted west in search of the Ocean Beach Pier in San Diego, and we found it in fine style after more than 2,000 miles on the Escort and rest stops in honky tonks, dive bars, ghosttowns.

Waits would be proud.