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"Highbrow Academy" is a film-within-a-film gag that appears in the season 21 episode "Bart Gets a "Z"". It appears to be a college-comedy film featuring a Rodney Dangerfield-style figure as its protagonist. The film has no known title: Highbrow Academy is the name of the college in which the action is set.
Edna Krabappel gets fired from Springfield Elementary after Bart spikes her coffee with alcohol. Feeling guilty, Bart later consoles himself that Edna has probably already gotten a job at a fancy private school. This is followed by a smash-cut to an apparent establishing shot of a school called Highbrow Academy, which carries the implication that Edna is now employed there. However, it is quickly revealed that this is an establishing shot from a TV film that Mrs. Krabappel is watching dejectedly in her apartment. The film features a Rodney Dangerfield-style character in a role similar to that played by the comedian in the 1986 comedy Back to School.
Bart visits Mrs Krabappel while she is watching the film. He attempts to offer her emotional support, but he is distracted several times by the film, which makes him laugh out loud.
The protagonist of "Highbrow Academy" is modelled on Rodney Dangerfield's appearance and persona. However, the design is distinct from that used for the character of Larry Burns in the season 8 episode "Burns, Baby Burns". Larry Burns was also based on Dangerfield's appearance and persona, as well as being voiced by the comedian, but since the character was revealed to be Mr. Burns' estranged son, the design featured a number of identifiable traits of that character, such as his long nose and receding hairline. The protagonist of "Highbrow Academy" is rounder in appearance and wears a varsity jacket and a college beanie. He is voiced by Hank Azaria.
The film-within-a-film appears to belong to the college-comedy genre, whose storylines typically centre on rowdy and boorish students who challenge the strait-laced reputation of the university they attend. Two scenes are shown. The first sees the protagonist arriving at the academy and meeting the dean. The second sees him gatecrashing an outdoor function whilst being pursued by a herd of piglets. Later in the same scene, a pig collides with him, causing him to destroy a large cake.
In his scenes, the protagonist makes a number of college-based innuendoes ("matriculate", "endowment", etc.) In his second scene, he breaks the fourth wall and speaks directly to the audience, saying "Hey, you're alright!". This is one of Dangerfield's signature catchphrases, and was used several times by Larry Burns in "Burns, Baby Burns".
The dean of Highbrow Academy resembles George Plimpton, who appeared as a cartoon version of himself in the season 14 episode "I'm Spelling as Fast as I Can". In that episode, it was revealed that Plimpton had played the dean in a college-comedy film called Boner Academy.