Drederick Tatum's prison time and return to Springfield was foreshadowed in Flaming Moe's (1991) when Tatum mentions being from Springfield and states, "That town is a dump. If you ever see me back there, you'll know I really (bleep)-ed up bad."
The writers admit on the commentary that they never resolved the plot about Bart's belt.
The fathers of Jimbo, Dolph and Kearney make their first and only appearances in the history of the show.
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. When Tatum makes his entrance; this was shot for shot recreation of one of Tyson's entrances. This was revealed during the DVD commentary by the director. The scene where Tatum is walking to the ring surrounded by shady characters is based on a real life photo of Tyson. 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.
In the scene in Moe's office, there is a brief shot of a poster advertising "Szyslak Vs. Oakley" and "Kirkland Vs. Silverman", referring to then-executive producer Bill Oakley and directors Mark Kirkland and David Silverman.