People who were out and about at various Chicago night spots on a night in September happened upon something surreal. They watched a throng of men and women, wearing frizzy wigs and identical oxford shirts, flood the neighborhood’s bars, drinking a round or two before moving on.

This was the third annual Bob Ross Bar Crawl, which is exactly what it sounds like: more than 50 people dressed as their hero, the public-television icon Bob Ross, paying tribute in tavern after tavern, 20 years after his death.

Jimmy Barrett, the event’s 26-year-old organizer, was 5 years old when Ross’s tutorial show, “The Joy of Painting,” was shown on 300 of 337 PBS stations nationwide. But while Mr. Barrett’s celebration of Ross may have once been driven by kitsch — a one-note Halloween party, writ large — his feelings for the man have evolved into a sincere appreciation.

“As a kid, it was just: ‘Oh, here’s a guy in an Afro, painting,’” said Mr. Barrett, a web development project manager. “I’ve gone back and watched some clips, and some of the stuff he says is oddly inspiring.”