Brian Wooden could teach us all a lesson in knowing thyself: The Nashville-based street artist, who grew up skateboarding and immersed in graffiti culture, always wanted to work in animation and fine art. Later on, as a student at the Savannah College of Art and Design, he found himself approaching realistic portraiture in what he calls a “soft, painterly way.” But, he says, he knew this path wasn’t true to his self.

“I wasn’t having much fun — it was just a little too serious for me,” he says. “So I made a hard transition one day and started going back into more illustrative work.” He returned to his passion for street art, composing massive outdoor wall murals with abstracted cartoon characters; his work is riotous, filled with...