The episode was written by Jonathan Collier, who is a huge boxing fan. Knowing that the people on the internet would "give them grief", the writers went to a lot of effort to explain how Homer would be able to challenge for the Heavyweight Title. A lot of the scenes involving Homer fighting hobos were pitched by John Swartzwelder. Lucius Sweet is a parody of boxing promoter Don King, and is voiced by Paul Winfield, who had previously played King in HBO's 1995 biopic "Tyson". In the script, Sweet was described as "A Don King type who looks and sounds exactly like Don King". The similarity is even pointed out by Homer with the line, "He is exactly as rich and as famous as Don King – and he looks just like him, too!" King was asked to guest star, but turned the part down. Drederick Tatum is a parody of Mike Tyson. The name came from George Meyer, who went to high school with a boy named Drederick Timmins, which Meyer thought was a cool name. Tatum having done time in prison is a reference to the fact that, at the time of the episode's production, Tyson had just recently been released from prison after serving three years for rape. Homer is at one point referred to as "The Southern Dandy" as a reference to the old-time boxers and wrestlers who had similar nicknames.