The announcer is legendary boxing ring announcer Michael Buffer, who voices himself.
The ring announcer introduces Fat Tony as "Anthony 'Fat Tony' D'Amico"; however, in "Bart the Murderer," his name was given as "William 'Fat Tony' Williams." He may have numerous aliases due to his mob connections though.
Above the boxing ring there is an advertisement for the Assassin shoes that Homer buys in the earlier episode "Bart's Dog Gets an F."
The match referee is obviously based on veteran boxing referee Mills Lane.
Homer encourages Bart to squeal after he gets beaten up by the bullies. This is contrary to the "code of the schoolyard" in "Bart the General" where Homer advises Bart to fight back physically against Nelson.
The Homer v. Tatum bout is a reference to the film Rocky, where a local champion faces the heavyweight champion.
A lot of the training sequences are based on the same movie, including Homer running alongside Moe, Marge asking Moe not to let Homer fight and the line "You will always be a loser."
The title of this episode alludes to the 1956 movie The Harder They Fall, the last film starring Humphrey Bogart. Its plot is the main inspiration for "The Homer They Fall". Bogart plays a washed up, cynical sports writer who agrees to lend his services to a criminal boxing promoter (played by Rod Steiger) by writing stories that make a star out of an untalented, naive Latino boxer whose fights - unbeknownst to him - are all fixed. When that system doesn't work any more and the boxer is about to be thrashed for good in what would surely be his last fight, Bogart's conscience reawakes. He helps the boxer escape to his home country of Argentina before the gangsters can take back all the money he won in his short-lived career. Moe's role in this Simpson's episode is in fact a combination of the roles played by Steiger and Bogart in the movie.
Just before the fight with Homer, Drederick is seen walking to the ring with a group of shady looking characters walking behind him. This is also based on a real-life photo of Tyson.
The character of Lucius Sweet is an obvious parody of Don King, a vicious boxing promoter. Homer even points this out with the line "He's one of the biggest names in boxing! He's exactly as rich and as famous as Don King, and he looks just like him, too!" King was also the manager for Mike Tyson.
It is possible that Homer's "take punches until they're tired, then finish them off" is based on Muhammad Ali's Rope-a-dope tactic.
The montage of Homer's victories mid-episode spoofs Raging Bull.
Some controversy has arisen about what song is exactly played during Homer's montage. DVD commentary of the episode has attributed the song to an original Alf Clausen composition. Some people alternatively have stated that it is "The Flower Duet" from Delibes' opera Lakmé. However, there is no passage in "The Flower Duet" song that convincingly matches up with the boxing montage scene, but it can be said that the song is done in the style and semblance of "The Flower Duet."
The song can also be a reference to Yanni's song "Aria", based off the music of Lakmé, and which was popular around this time due to its heavy usage in British Airways advertisements.
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.
Drederick Tatum's theme song is "Time 4 Sum Aksion" by Redman. It was the same song chosen by Mike Tyson for his first fight upon his prison release.
The closing song is "People" sung by Sally Stevens.
The scene in which Homer and Moe go to the fight is a reference to the video game Punch-Out. That being said, both media have a boxer in training and have their respective trainers ride a bike. In the episode Moe appears to ride a scooter.
Homer asks Moe about Tatum, "Is he another hobo?" This implies Homer doesn't know who Tatum is. But in Season Two, when Homer stole cable, he invited a bunch of people over to watch "The Big Tatum fight." Unless he hadn't known it is Drederick Tatum.