The playbill for the January 19 taping of Oregon Public Radio’s Live Wire! — an old-time radio show modeled loosely after National Public Radio’s Prairie Home Companion — gives John Callahan top billing. For most everyone at Portland’s Aladdin Theater, it is the first time they have seen Callahan’s name paired with the words “singer/songwriter.” The crowd, 650 strong, is standing room only.

When Callahan is introduced, the Aladdin erupts with applause and cheers. He rolls to center stage, dressed grunge/casual. Beneath his worn jacket is a faded T-shirt with one word subtly visible: “Trash.” Callahan’s wheelchair armrests are liberally wrapped with black electrical tape. His accompanist, Chris Hubbard, settles in behind a shiny black grand piano. After an embarrassing moment when he has to ask a stage hand to adjust his microphone for him, Callahan looks around, squinting at the balcony seats, sizing up the crowd. “I thought they were supposed to have a little mark here,” he deadpans, gesturing toward a spot on the stage floor, “where I could throw up.”

Laughter. Tension released. This is the Callahan everyone knows, the cartoonist with the dark wit. “My first song is titled “Suicide in the Fall.”” A few people titter, then an uncomfortable silence settles in. “It’s not as uplifting as it sounds,” he says. More laughs.

After a simple medium-tempo piano intro, Callahan launches into the lyrics:

There’s trouble in the steeples
And the crows are set to fly
But there’s apples in the baskets
And a dead moon in the sky.

His voice, innocent, unadorned, creates a mysterious contrast with his often dark lyrics. The effect is suspenseful, as the audience waits for the song to declare itself. Will he make a joke of suicide? Is he serious? You can almost feel a sigh of relief from the audience when the lyrics reveal the artist’s intent:

Well, there’s something about the softness
Of the colors on the wall
That keeps me from committing
Suicide in the fall.

When the song ends, there is generous, respectful applause. The crowd is catching on. They are witnessing the evolution of Callahan the musical artist. His single-frame gags have somehow given way to a CD of songs — “Purple Winos in the Rain” — that at times seems almost uncomfortably honest and melancholy, yet somehow charming, and always melodic.

When the applause dies down, emcee Courtenay Hameister sits next to him for an interview, drawing upon his past cartoons for comic relief, gently probing about his new artistic venture, and making entertaining chit-chat. After the interview, Callahan closes with his signature song, “Touch Me Someplace I Can Feel”:

Life is hard but death is worth it
Nothing’s certain, nothing’s real
Give me something cheap but perfect
Touch me someplace I can feel.

Callahan lives in a Northwest Portland apartment a short power-chair jaunt off NW 23rd — known locally as “trendy-third” — a 19-block run of bustling boutiques, natural foods restaurants, kosher delis, inner-peace-love-tarot-card-reading-artsy-shoppes and anti-Bush signs in sash windows. Callahan, 56, whose eight books of cartoons have established him as a master of political incorrectness, lives smack dab in the middle of liberal Americana, two blocks from the local abortion clinic. There are at least four Starbucks within easy rolling distance.

I drove there on a snowy day in January. Once on busy NW 23rd, I began worrying about finding a parking space, but first I had to find Callahan’s apartment building. Bingo — a perfect set of power chair tracks embedded in the sidewalk snow traveled up Lovejoy from NW 23rd.

After parking and transferring into my manual chair, I aligned my wheels in Callahan’s tracks and followed the trail he had blazed to a side door on an older three-story brick building next to a debris-filled dumpster. I knocked and waited a full four minutes for his attendant to respond. He had been busy getting Callahan ready to meet me at 2 p.m. in the afternoon — one of three attendants who rotate off and on. Callahan lives independently but needs help part of each day, which costs a pretty penny. His income from royalties disqualifies him from assistance of any kind.

I was surprised to find his twin bed just inside the door in what I assumed was his living room, with almost no furniture other than an upright piano. The one-bedroom apartment was small, dark, stripped to essentials. Sitting in his older power chair next to a too-tall breakfast bar, Callahan told me he no longer owns a computer — he had thrown it away — “but I’m getting a lot of pressure to get one again, since the CD came out.” His mammoth fluffball of a cat, Biggie, eyed me from the comfort of Callahan’s bed.

I tell Callahan that people are surprised when they hear of his CD, but I’ve recently re-read his autobiography, where just before his accident, at age 21, he describes himself as having a “creative artist, poet, and songwriter hidden within.”

“It’s something that’s always been growing in me,” he says. “I’ve always wanted to be a songwriter. The points just never connected back then. I was playing guitar very well at 18, 19, 20, and I’d try to write songs but I was such a little alcoholic, and I could never get the words together right. Took me until I was older, in my 30s and 40s, to start writing songs, and then I had to learn how, with my fingers, to play the piano a little bit again, and play sort of open tuning on the guitar. I could always play harmonica. I didn’t have to learn that, it was just natural.”

Does this mean he’s de-emphasizing cartooning now?

“No, no,” he says. “Just doing music and stuff in addition. But I wouldn’t mind developing my music and becoming more of a performer and traveling around. But in an easier way than a plane. I don’t like planes because they can wreck your wheelchair. Every time I ride in a plane they smash it, they always somehow damage the wheelchair or send it to the wrong place. I don’t feel like dealing with that stress. And a train I don’t know about. Maybe having one of those big rock-and-roll buses or something would be cool. I could just stay in bed. Each town I could just sing out the window of the bus and go to the next town.”

And then I ask the question that’s been nagging at me. I’ve read elsewhere that he lives off his royalties, but his apartment is, well, basic. “How are you doing economically?”

“Oh, doing OK. It’s sometimes big, sometimes not. It varies so much with me. I don’t even pay much attention to money. I just do what I want to do creatively, and the money always follows. I’ve always been lucky that way. I just never look down from the high wire and I’m OK.”

Where His Songs Come From
There’s a hint of “Purple Winos in the Rain” in his autobiography as well. In the concluding pages, after he has faced down his alcoholism six years following his accident, he describes what he sees while rolling past St. Mary’s Cathedral one evening: “It looms high above me in the night with its sculpted saints and the peaceful face of the Blessed Virgin above the ten broad doors. … I can hear the bell sounds, broken by the wind, and the rain is stinging my face. … The winos are crouching in the little shelters that the doors and buttresses of the church provide …”

References to street life are sprinkled throughout Callahan’s songs. In his daily rounds in his power chair, especially whenever he ventures as far as “Old Town,” where Portland’s homeless people, drunks, addicts and prostitutes hang out, Callahan must literally swerve to avoid running over people sprawled on sidewalks. The rest of us roll up our windows as we drive by, safely insulated.

Callahan’s focus on street people seems part of a deeper connection. “Yeah, I think that’s true,” he says. “I don’t have any lines of delineation between classes and people. I feel it internally. It’s an illusion to think there are lines. It’s all one thing.”

Callahan’s egalitarian worldview may come from an awareness that he might have been a homeless drunk himself, had he not hit bottom, wrestled and reconciled with his Higher Power, and stopped drinking. “It was a touchstone,” he says. “I had a bottoming out experience, a dramatic reckoning with God, but then years later I had another experience, 9 or 10 years ago, more of a self-realization kind of thing. Long story short, they messed up a surgery and I got a staph infection. It almost killed me and I had to be put under, kept down on machines and alive for about a week, it was terrible. But a couple months after that I woke up in my home and I just sort of moved into this space where there was just nothingness and bliss, maybe just for a few minutes. I mean, once you have an experience like that, it’s almost like having what they call ‘free samples.’ And you just have a very easy time believing.”

Now he says he is looking for a way to channel some of his energy into helping people. “Kind of a benefactor project to get involved in,” he says. “Someone said maybe suicide prevention or something, since I have so many references to suicides in my songs, but that’s a really heavy, heavy subject to have attached to your life.”

The songs on his CD, written over the last 10 or 15 years, he says, are organic, driven by his need to create. The project was a collaborative effort with local blues guitarist and producer Terry Robb. “I ran into him one day at a guitar shop and told him I just finished writing a bunch of songs,” says Callahan, “and I wondered if he’d just like to take a look at them. And he said, ‘Well let’s just go in a studio and do it.’ Maybe 15, 20 years ago I did one of his album covers [Next Window, 1985, out of print]. It’s been a mutual admiration society for years.”

“He’s one of the few people I talk to,” says Robb.

In fall of 2005 Callahan and Robb began laying down tracks at Falcon Recording Studios in Portland. Robb’s guitar work is well known in Northwest blues/R&B circles. He also plays bass and percussion on the CD, while Callahan sings on every track, occasionally plays harmonica, a lap-held open-tuned ukulele with a slide on one finger, and simple piano chords. The recording is rounded out with local musicians and background vocalists. All melodies and lyrics were written by Callahan, while Robb handled the production end — charting, arranging, mixing, coaching Callahan, hiring musicians.

The CD wasn’t released until November 2006. Music Millennium on NW 23rd, an institution among music stores in Portland, was the perfect venue for one of the neighborhood’s best-known and best-loved residents to make his debut as singer/songwriter. The performing area features a full stage and a comfortable, informal “living room” — a couple of couches, some chairs, but most people stand and listen. “There were 100 people or more for his release, a really good turnout,” says MM’s assistant manager, Davis Cain. “He was nervous, you could tell. But the crowd really loved him. A lot of people who were here were people from the neighborhood, almost like playing for family and friends. When he sang ‘Touch Me Someplace I Can Feel,’ I broke into tears.”

“It was so intimate,” says Callahan. “There was a tremendous loving feeling from the audience.”

Cain says Callahan comes in almost daily while rolling through the neighborhood. “He likes to sit and soak in the vibe and just disappear. I think it’s a place of solitude for him. Sometimes he’ll bring in his cartoons before they’re published. We’ll pass them around and laugh or tell him when one isn’t funny. I really appreciate the depth of his wisdom,” says Cain, “the way he sees people. That’s his job, to observe people and point out when they’re being hypocritical or false.”

The feedback from Callahan’s Live Wire! performance has been “all positive,” according to the show’s producer, Robyn Tennenbaum. “I think most people were surprised by the person and the voice behind the cartoonist. People have been comparing his music to John Prine and Leonard Cohen.”

Some who aren’t particularly taken by Callahan’s music cite a sameness to his songs that can become monotonous, but even they recognize certain songs as being pretty, with complex lyrics and promising potential for being covered by established artists.

The most consistently positive comments seem to come from those who have seen him perform live, perhaps because of the element of suspense. “I realize those songs are kind of theatrical,” says Callahan. “Like when I sang ‘Touch Me Someplace I Can Feel’ at the Aladdin, it was a neat feeling to say, ‘Thank you, good night’ — and kind of pull back into the shadows. It’s very dramatic,” he says. “A whole new way to manipulate people.”

Callahan on Film
Dutch documentary filmmaker Simone De Vries was surprised when she came to Portland to film the cartoonist last summer and found that he had recorded a CD. “It was a bonus,” she says. “I was mainly interested, at first, in his cartoons and life.” But she recognized the inherent drama of “Touch Me Someplace I Can Feel” — and chose it for her film’s title.

The film made its American debut at the Portland International Film Festival on Feb. 11. De Vries was there along with Callahan, who was busy greeting people and signing autographs before the showing. Portland director Gus Van Sant (Good Will Hunting), a friend of Callahan’s, was conspicuously present in the front row.

From the opening scene the film is captivating. Callahan’s face is shown in extreme close-up, from below, peering over his sketching pad as he works outside on a sunny day. Throughout the film numerous close-ups capture Callahan’s wry sense of humor, blue eyes and moonscape-craggy face, which at first seems intrusive but gradually becomes part of the Callahan mystique. “I know I need a new dermatologist, that’s for sure,” quipped Callahan as he took questions following the showing.

The film is built around repeating elements — objections to his cartoons (being read off-screen), followed by the objectionable cartoons themselves (much laughter from the audience), an over-the-shoulder camera that follows Callahan in his power chair around Portland, and scenes where he sings, sometimes spontaneously.

Voice-overs document his early days following his accident. Callahan says at first his quadriplegia made him feel like a floating head. Then his attempts at describing his paralysis and lack of sensation dovetail into political humor: “You can get used to almost anything, except for Bush’s administration, and then you really have no feeling.”

Some of the biggest laughs accompanied a panel of his early cartoon work showing a quad trying to free himself from having oral sex with a huge lady who is sitting on his face. The more he struggles, the more she interprets his frantic head movements as passion, which fuels hers. The cartoon culminates with a newspaper boy hawking a paper with the headline, “Local Quad Smothers in Cunnilingus Accident.”

In one scene, the camera eavesdrops on Callahan asking a woman on the street if he can draw her nude. She poses in his apartment, with Callahan directing her to sprawl on the kitchen counter with her legs spread in front of him. He then draws, unbeknownst to her, an unflattering portrait, with her labial lips exaggerated (the camera cannot see the real thing because the lighting is so dark). Then, still drawing, he “inserts” a miniature quad-in-a-wheelchair holding a drawing pad, into her vagina.

He says that drawing nudes is important to him, that the contact is a kind of healing experience.

Callahan on the Street
The documentary captures Callahan letting his anger out when he shows up to sing at a rock club at 7 p.m., as directed, and finds out he won’t go on until 10:30. He explains that he can’t just sit around for three hours doing nothing, that he’s prone to pressure sores from too much sitting. He is clearly pissed off, calling the place “disorganized.” No thought has been given to how his wheelchair is supposed to access the stage.

He leaves without performing, and back in his lift-equipped cab, camera rolling, throws up his hands, as if to say, what can you do? Then he holds up one hand for the camera, palm toward his face, fingers extended, and says, “I’m trying now. See all my fingers here. Now block out the index finger, the ring finger, pinky and thumb.” Callahan has invented the imaginary Quad Finger — intended for the club’s management — making a joke out of an ignorant act of discrimination.

The film was very warmly received, with much laughter and appreciation of Callahan’s transparency and sense of humor. Both De Vries and Callahan took questions after the showing. One questioner remarked that most of the scenes seemed to show Callahan in and around NW 23rd. “Do you ever travel much or go other places?”

“I’m thinking of making a trip down to 18th,” quips Callahan, “but it’s just in the planning stages.”

A few days later in a phone interview, De Vries tells me, “When I talked to him [on the phone] the first time, I expected him to be very abrasive, cynical, because of his cartoons, but he is nice and sweet and polite, even saying he was honored that I would make a film about him.”

“The film has me going back to work all the time,” says Callahan. “Always writing, always working. I kind of like that.”

“How he looks at other people, that’s what the film is about,” says De Vries. “His ability to capture something in a single frame with a very sharp eye, I like that. A very skillful art, somewhat underrated. What he says in one picture I need a whole movie to do.”

De Vries says she hopes Touch Me Someplace I Can Feel will play at other film festivals and eventually air on television in the United States. “Maybe on HBO or PBS,” she says, “and then be available on video so everyone can see it.”

She says that Callahan’s music is very different from his drawings, yet in some essential way, it is the same. “He is still looking at the same people, but in a different way, a melancholic, sweet, and beautiful way. He has a sort of radar that draws him to people in need. He knows the people on the street and they all know him.”

And then she relates a story. “We were in the street filming and a homeless guy comes up and says, ‘Oh, John, John, I heard your song on the radio’ — it was ‘Purple Winos in the Rain’ — and John says, ‘Here, let me give you one of my CDs.’”

He’s like that, say his friends and acquaintances — generous, approachable.

“And later,” continues De Vries, “after the homeless man has gone, John says to me, ‘Now someone has to give him a CD player.’”