When I met him late in his life, in January 2007, there was snow on the ground. I opened the door to his apartment and found him in bed. The room was dark, stuffy, small. I felt instantly claustrophobic. A writer from Willamette Week, Beth Slovic, had just done a piece on him entitled, “Tales From the Crip.” It seemed like an apt title.

I followed his brief career as a one-CD singer/songwriter: attended his performances; met and interviewed a number of people who knew or played with him; visited him and talked on the phone with him, often for more than an hour. He opened up, told me he had lost interest in cartooning. I urged him to continue drawing and gave him work, fed him ideas. He told me about his life, his dream for the future, his disappointments and triumphs, and almost as an afterthought, pumped out several cartoons.

When he first mentioned that he was thinking of applying for graduate school and going into counseling, I almost laughed in his face. I thought he was joking. Callahan, the rapier wit? How would he ever stomach those dull psych classes? He was light years beyond that.

The better I got to know him, the more I realized he was serious about starting over. He wanted respect, but he also wanted to do something that had a lasting effect. He wanted to help people.

I know, that doesn’t fit with who we think he is. He’s Callahan the alcoholic, first-of-his-kind, outrageous, irreverent, angry social critic/male chauvinist cartoonist. Wrong. He’s Callahan the perpetual student, bleeding heart, do-gooder, substance abuse counselor, sensitive listener. Wrong again. He’s bitter, resentful, suspicious. No. He’s grateful, giving, trusting.

He was all of this, yet none of it could define him. Most of all, he was vulnerable, and by the time I became his friend, I suspect he knew he didn’t have long to live. I felt it, too. It was in the air. When we talked, we were uncomfortable, knowing that we both knew.

He appealed to artists on the edge: Robin Williams, Tom Waits, Kinky Friedman, John Prynne. He seemed like a man of the world, yet he hardly ever left Portland. His idea of a major trip? Hire a cab to drive him to the coast, 90 minutes distant. After the release of his CD, he deadpanned the story of someone suggesting he go on tour, amused at the image of himself hanging out of a bus window, waving at strangers welcoming him to middle America.

He was content living right where he was, on Northwest Trendy-Third in the City of Rain, amid a tight neighborhood of nouveau hippies, liberal thinkers, street buskers, homeless scroungers and gourmet restaurateurs. He wore his flaming red hair like a communist flag. It flapped in the wind when he sped down Lovejoy in his battery-powered chariot. When it started to fade to gray, he colored it a deeper red. His face was a broad avenue pocked with potholes, yet a certain type of woman felt comfortable parking there. His level gaze, bluer than blue, was other-worldly. He was a God-loving heretic. A rebel artist. He was Callahan.