[3] He was a visual artist long before he developed an interest in music, and produced hundreds of intricate, unusual, colored ink-pen drawings,[3] most of them depicting Chicago streetscapes; he frequently sold these on the street for between $20 and $40.

[14] In Artist of the Streets, he was shown walking through Chicago's Loop neighborhood, producing his ink pen drawings outside of the Marshall Field and Company Building, and interacting with people curious about his art.

The band developed a popular underground following as well as attention from musicians such as Eddie Vedder, Henry Rollins, Mike D., Jello Biafra, and the members of White Zombie;[16] and soon caught the attention of Rick Rubin at American Recordings,[16] an independent label distributed by Warner Bros. Records.

During his many tours and live appearances, Willis became "famous for greeting fans with a headbutt"; this left him with a distinctive permanent bruise on his forehead.

A blind demigod with the power of far-sight and half-brother to Wonder Woman, his physical appearance and mannerisms are based on Wesley Willis.

[19] Willis has been honored with a star on the outside mural of the Minneapolis nightclub First Avenue,[20] recognizing performers that have played sold-out shows or have otherwise demonstrated a major contribution to the culture at the iconic venue.

[22] "Hellride" was the term used by Willis to describe his encounters with "demons" (delusions brought on by schizophrenia),[23] which occurred mainly on the CTA bus lines in Chicago.

[24] As a solo artist, Willis filled his albums with funny, bizarre, tense, and often obscene statements about crime, fast food, cultural trends, bus routes, violent confrontations with superheroes, and commands for his "demons" to engage in bestiality (in The Daddy of Rock 'n' Roll, Willis explained that these songs would "gross out" the demons enough to make them leave him alone).

[13] Critic Stephen Thomas Erlewine of AllMusic wrote that despite Willis' prolific output his songs were essentially variations on the same simple structure, melody and lyrical themes.