This episode's title is a play on the book The Boys of Summer, which dealt with the legendary Brooklyn Dodger baseball team of the 1950s and was also a nickname for the team. There is also a song with the same name by Don Henley (later covered by The Ataris).
It is revealed that Springfield has held the record of being the "Meanest City in America", which is apparently backed up for the town's treatment of Bart's losing their game against Shelbyville.
The episode's plot borrows from the movie The Best of Times, in which an old football game is replayed.
The episode is extremely similar to an episode of the Stephen King miniseries Kingdom Hospital, entitled "Butterfingers". In the aforementioned episode, Earl Candleton is playing in the final game of the World Series, and although he has had a stellar career that season up until that moment, just like Bart, he drops an easy pop fly that means the difference between his team, the Robins, winning or losing the game (they lose.) He is abused and scorned by fans just like Bart, although his torment extends over years; he is given the scornful nickname 'Error' Candleton and 'Butterfingers,' and people throw baseballs at him wherever he goes. Like Bart, he is given a chance to replay the critical moment of the game (although in his case, it is due to the intervention of supernatural forces; also unlike Bart, the second time around, he catches the ball on the first attempt).
The instrumental theme played while Bart watches the fly ball in the air is the main theme from the film Rudy.
Bart having the ball spin him in a circle while his clothes fly off is a reference to Charlie Brown in Peanuts.
Bart can be seen wearing his baseball glove on his right hand in this episode, once again showing that he is left-handed, like Simpsons creator Matt Groening.
The signs in front of the baseball field read: "Springfield Little League Park" and "Warning: Your child is not as good as you think he is".
The announcer for the softball games was Vincent Edward "Vin" Scully. He's the same announcer for Los Angeles Dodgers. Harry Shearer (the voice of Vin Scully) also played Vin Scully when he was a cast member on Saturday Night Live during his second stint on the show (from 1984 to mid-1985).
The two radio stations shown in this episode were both KBBL 970 AM and QUE BBL 640.
It took 78 tries for Bart to catch the game winning ball.
According to this episode Bart's favorite song is "Love Stinks" by The J. Geils Band.
According to this episode, Bart came out blue-colored and backwards when he was born (which actually would have killed him).
Springfield has a junior baseball team called The Springfield Isotots.
The last time a sport-related misfortune lead a Simpson to become a pariah and attempt suicide occurred in "Million Dollar Abie".
The episode received mixed to negative reviews, probably because the citizens drives Bart crazy to the point where he tries to commit suicide. Some critics gave the episode a positive rating, while others average.
It might be probable that the episode also had the intention of remark some similarities between Bart's treatment after the game with the actions that, in real life, and after the infamous 1950's FIFA World Cupfinal match between Brazil and Uruguay, Brazilians took against their team goalkeeper, Moacir Barbosa, who was been pointed as an scapegoat for having not avoided the last (and victory) Uruguayan goal being scored - this incident would later synthetize what novelist Nelson Rodrigues would call the "mongrel complex" ("complexo de vira-lata"), alluding to Brazilian people's overall lack of self-esteem at the time.
Ned Flanders angrily telling Rod to do what he is told and lashing out at him while removing the word "I Hate Bart Simpson" on his fence is similar to how he lashed out at all of the Springfield residents, including Homer after they crudely rebuild his house from "Hurricane Neddy".