Bemused by the culture of confession and self-help fostered by the likes of Oprah Winfrey and Geraldo Rivera, he was uninclined in his work to be outwardly sympathetic to the afflicted or to respect the boundaries of racial and ethnic stereotyping, and his cartoons were often polarizing: some people found them outrageously funny, others outrageously offensive.
I think Callahan, who never achieved any significant degree of commercial success, was the first and best to apply such darkness to the comics; this sort of edge is now almost mainstream. If you watch “Family Guy” or “South Park” or “American Dad,” you will see that they are Callahan’s children. (…)
He grew up in Oregon as a teenage alcoholic. He was 21 and drunk — a passenger in a car driven by another drunk who fell asleep at the wheel — when the car hit a wall at 90 miles an hour, and Callahan’s spine was crushed. Even that didn’t stop his drinking.
He stopped one day six years later when he was in his wheelchair, trying to gnaw the cork out of a bottle of wine with teeth chipped from battle with so many corks. The bottle slipped out of his clawlike hands and rolled away on the floor to where he could not reach it. He burst out crying. In that moment, he saw the ruin of his life as a pathetic parable. He never took another drink.
If you search for Callahan art on the Web, the one that you find most often, unfortunately, is a cartoon that never should have been published. It came in one day, Tom looked at it, blanched and immediately faxed it to me — by then, I had left the Herald for The Washington Post.
The cartoon was an almost unimaginably crude gag at the expense of a teenage Martin Luther King Jr. — so tasteless that The Post’s editors won’t let me repeat it here.
Tom and I both laughed — not at the joke, which was hideously offensive and not even particularly good, but at the wonderful tone-deafness of Callahan, who simply had no idea that there was a line — let alone where that line might be.