Startled, I glanced in my rear view mirror and saw the man in the car behind me, mouth open all the way back to his tonsils, belting out the Bill Withers classic. “That voice,“ my old singing teacher would have said, darkly, “shouldn’t be allowed to sing.”

It was after midnight and I was lost on the road, looking for the way home. I’d seen the glow of double arches in the distance, found a 24-hour McDonalds underneath and stopped at the drive-thru window to buy a bottle of water and ask for directions. McDonalds’ midnight shift employees aren’t hired for their geospatial sense, so my query kicked off a 10-minute search for someone who actually knew how to find I5 South.

The singer pulled in behind me while I waited, in his rickety old Datsun that had definitely seen better days. Its bright red had faded to piebald pink-and-rust and the side mirror was reattached with what looked like a coat hanger. Another served as a radio antenna and one headlight was gone, literally (there was a hole).

The guy behind the wheel matched his transport: Gaunt and rawboned, scanty beard, thinning shoulder-length locks shot with grey. His eyes were closed, head thrown back. One arm flagged the time as he sang and each time it waved, the ragged hole at the shoulder of his faded tee flashed fishbelly-white skin.

He was one of the legions of glassland residents that a friend calls “time-warp hippies.” Visit Portland’s Saturday Market and you’ll see them out in force; the genial, grey-haired folk in ponchos and old cords who will still sell you a hand-made hashpipe or tie-dyed shirt. “These are the guys,” mused a local colleague, ex-hippie himself, “that just never needed to grow up. Sometimes I envy them.”

My guy’s voice soared and swooped, banging around the right notes without ever actually nailing one; any meter or rhythm was at best wishful thinking. I’m a huge fan of “Ain’t no sunshine,” and by rights I should have been wincing at the scritchy butchery going on behind me.

Instead, it shook me to the bone.

This dude couldn’t sing, not a note, but by God he could SING. I stared at him through the rearview mirror, watched the restaurant fluorescents glinting off the tears slipping down his cheeks. His voice faltered and broke, sobbed and wailed. He sent his pain out into the night and hit me foursquare between the eyes.

It brought home what all great blues singers know instinctively: Pain isn’t pretty. There’s a world of difference between a smooth and supple stage performance, every note correctly and effortlessly slotted into place, and a song like his, forcibly ripped from a despairing gut.

I wondered what was behind that song: Was he mourning a lost lover? Was he a maudlin drunk on a three-day bender? Or was this song so powerful–for him–that that it ripped him apart all by itself?

He caught me staring at him from the rear view mirror, and grinned. He raised an imaginary glass in my honor and mimed a toast. Then he blew me a kiss.

The singing stopped. I got my directions and left.