John Wayne Gacy “Hi Ho in the Winter” Painting
“Hi Ho in the Winter” is an original prison painting by convicted serial killer John Wayne Gacy, created while he was incarcerated for the murders of 33 young men and boys. The scene portrays the Seven Dwarves moving through a frozen landscape, their bright colors and playful gestures sharply contradicting the violent reality of the artist’s crimes.
This disturbing contrast is a defining trait of Gacy’s artwork. Throughout his imprisonment, he repeatedly returned to childlike imagery—storybook characters, clowns, and fantasy scenes—produced with a naive style that masks the brutality behind the hand that painted it. The winter setting, with its barren trees and cold tones, adds an eerie stillness beneath the surface innocence of the composition.
Signed “J.W. Gacy,” Hi Ho in the Winter stands as a chilling example of true crime outsider art: an object where innocence is performed, not felt. More than a painting, it is a psychological artifact, and an unsettling reminder of how darkness can exist behind a carefully painted smile.
Hand signed in oil paint on the front, and signed, titled and numbered on the back in pen. Included is the original plastic wrap that the painting was wrapped and sent in by Gacy. This oil painting measures 16x20 and comes professionally framed.
COA included
John Wayne Gacy (March 17, 1942 – May 10, 1994) was an American serial killer and sex offender who became one of the most notorious criminals in U.S. history. Active primarily between 1972 and 1978, Gacy was convicted of murdering at least 33 young men and boys in Cook County, Illinois. He lured many of his victims to his home with the promise of work or companionship before sexually assaulting, torturing, and killing them. Most of the victims were buried in a crawl space beneath his suburban Chicago residence.
Gacy was well-known in his community as a successful contractor and active civic participant, often performing at local events dressed as “Pogo the Clown.” This double life contributed to the public shock following his arrest in December 1978. In 1980, he was convicted on all counts and sentenced to death. After spending 14 years on death row, Gacy was executed by lethal injection at Stateville Correctional Center on May 10, 1994.
