Jump to: Spoilers (1)
Drederick Tatum's prison time and return to Springfield was foreshadowed in The Simpsons: 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."
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The writers admit on the commentary that they never resolved the plot about Bart's belt.
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The fathers of Jimbo, Dolph and Kearney make their first and only appearances in the history of the show.
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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.
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Above the boxing ring there is an advertisement for the Assassin shoes that Homer buys in The Simpsons: Bart's Dog Gets an F (1991).
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According to the writers on the DVD commentary, this episode is pretty much the season seven episode The Simpsons: Homerpalooza (1996), only it's centered on boxing rather than popular music.
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Lucius Sweet is a parody of boxing promoter Don King, and is voiced by Paul Winfield, who had previously played King in Tyson (1995). 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.
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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.
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The song during the closing credits, which is a montage of Moe helping people around the world with the Fan Man's Paramotor is "People", a song from the 1964 Broadway musical "Funny Girl", starring Barbra Streisand.
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Whenever designing rooms, Mark Kirkland tries to show a bare lightbulb because he feels that it makes things more depressing.
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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.
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Fat Tony is introduced as Anthony D'Amico. When he was introduced in "Bart the Murderer", his real name was said to be William Williams.
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The title is from the old proverb: "The bigger they are, the harder they fall", as well as 1956 boxing movie "The Harder They Fall".
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At one point in the episode, the screen freezes and turns to a black and white view of one of Homer's boxing opponents falling out of the ring. This scene is a parody of the 1924 painting Dempsey and Firpo by George Bellows.
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A lot of the scenes involving Homer fighting hobos were pitched by John Swartzwelder.
In preparation for this episode, Mark Kirkland watched several boxing films and is satisfied with how it turned out.
The black and white montage of Homer's victories, accompanied by angelic classical music, is a nod to a similar scene in the boxing movie Raging Bull.
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.
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The basic premise is borrowed from the original Rocky (1976): an amateur boxer is plucked from obscurity to face a brash, cocky heavyweight boxer.
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