Robert Underdunk Terwilliger Jr., PhD – otherwise known as Sideshow Bob – made his first appearance in The Simpsons in Season 1 – Episode 8 “The Telltale Head.”
Voiced by Kelsey Grammer, Sideshow Bob was sent to prison due to Bart foiling his plan to frame Krusty the Clown for armed robbery. After being put away, he had nothing but revenge on his mind which has made for some rather thrilling (rather than the usual comedic) episodes over the years.
Along with Mr. Burns, Sideshow Bob is one of the more evil characters in The Simpsons universe; if horror movie tattoos are anything to go by, people love the bad guy!
While he hasn’t appeared in as many episodes as some other characters, the images below will show you that it is still possible to get a unique Sideshow Bob tattoo.
The Tattooed Archivist 