Krusty getting harassed during a restaurant sketch and suddenly breaking character is reminiscent of the infamous moment on ABC's 1980s sketch comedy showFridays where Andy Kaufman harassed then-cast member Michael Richards over refusing to stay in character during a sketch about restaurant patrons ducking into the bathroom to smoke marijuana during a dinner date and gets into a fight with him. There are stories debating whether this was staged or real that persists to this day.
This moment was also seen in the 1999 Andy Kayfman biopic Man on the Moon., with Jim Carrey as Andy Kaufman, Norm MacDonald (formerly from Fridays' rival show, Saturday Night Live) as Michael Richards, and Caroline Rhea (from the sitcom Sabrina, The Teenaged Witch) as Melanie Chartoff.
Krusty's line "Our Chimpendale's dancer's gonna give you the full monkey!" references the 1997 film The Full Monty.
A picture of Krusty and Bob that was unveiled while Krusty was lamenting his cruel treatment of Bob closely resembles the cover of Simon and Garfunkel'sBookends.
The scene where the two executives of Krusty's show reform into a silvery mass after being blown up references a similar ability the villain from Terminator 2 possesses.
In his cosmonaut gag from 1957, Krusty identifies himself as "Kaputnik." Roger Kaputnik is the perennial hypochondriac created by MAD Magazine writer Dave Berg for his "Lighter Side..." series.
Chief Wiggum references George W. Bush when witnessing Bart using a Bat to vandalize a Krusty statue on Sideshow Bob's orders. He say's "It's so great seeing a kid use a wooden bat. These days, it's all aluminum this, and George W. that."
It should be noted that this is the first time the Simpsons made a Bush joke since his inauguration into office.
Also of note is the fact that this scene has been edited in syndication.
Bart mentioned that he had defeated Sideshow Bob 6-0 in this episode. In reality, it should have been 5-0. Brother from Another Series wouldn't count, since Sideshow Bob wasn't the one who instigated a crime in the episode (it was his brother Cecil), and Bart wasn't even the one responsible for sending him back to jail.
Day of the Jackanapes was released four years after Brother from Another Series, the previous Sideshow Bob episode, making the time in-between the two episodes the longest cooling-off period Bob ever had.
Krusty reveals to been on air for 61 years, but in I Love Lisa, Krusty celebrates 29 years on air.