This story appears in the May 2016 issue of Playboy. Subscribe

Like many 1980s skate punks, I discovered Raymond Pettibon through his album covers, his flyers and, of course, his iconic Black Flag logo, which may be the most tattooed signifier of cool ever created. But I loved Pettibon’s work beyond its association with a band or a subculture. I recognized his understanding of the figure and his restrained mark-making coupled with his amazing gift for lettering, all of which allowed him to transcend the labels of graphic artist, illustrator and comic book artist. Pettibon’s work taught me to present the most minimal but the strongest elements, to focus on what gives things their essence and power, and to be fearless. He thrives on challenging the status quo, and his art frequently contains symbols and insights that people find difficult to discuss—at least until someone else breaks the ice. You find this in comedy, whether it’s Lenny Bruce or Dave Chappelle, but far less often in the art world. In many ways, Raymond Pettibon is a master of black comedy: His poetic imagery seduces you, and then it cracks you over the head.

From left to right: No Title (Jesus saves. The…). Pen and ink on paper, 14 x 10½ inches, 1986. No Title (The cards couldn’t…). Pen and ink on paper, 11¼ x 75/8 inches, 1992.

From left to right: No Title (Whatever it is…). Pen and ink on paper, 18 x 12 inches, 1991. No Title (The fighting got…). Pen and ink on paper, 30 x 22¼ inches, 2001.

No Title (The war, now…). Pen, ink, gouache and acrylic on paper, 24 x 19 inches, 2008.

Top left: No Title (Taking a bath…). Pen and ink on paper, 11 x 8½ inches, 1986. Top right: No Title (I have enlarged…). Pen, ink and gouache on paper, 18 x 24 inches, 2008. Bottom left: Black Flag at the Starwood. Offset print, 8½ x 11 inches, 1980. Bottom right: No Title (Bring out with…). Pen and ink on paper, 22 x 17 inches, 1990.