Bart's fall over the cliff references two past Simpson moments. First, Bart falling on the rocks references Homer's famous fall over Springfield Gorge in "Bart the Daredevil". Second, the idea of having a Simpson use a dummy over a cliff to fake their death was used by Homer in "Mother Simpson".
The premise of this episode resembles one of the original plotlines for "A Milhouse Divided", where Bart nearly separates his parents due to attention Milhouse got relating to his parents' divorce. The only differences are that in this episode, Bart's parents nearly being separated was an accident instead of the intended result, and in this episode, it was actually Milhouse's idea instead of Bart's as he liked the attention he got from when his parents were fighting over him and feared losing it if they got back together.
Drederick Tatum is seen attending the AME church at the beginning, even though Mike Tyson, whom Tatum is based on, is a Muslim.
The term "Pox Box" is a play on the former name of 4Kids TV, Fox Box.
In the scene parodying The O.C., in addition to the cheating scene, it also involves the O.C. gang going to Knott's Berry Farm (along with a person dressed as Snoopy), with The O.C.'s theme song California playing (Snoopy then forces the O.C. kids to take out money from an ATM at gunpoint). California is also played over the ending credits.
In one scene, Bart and Milhouse are acting out a song from the play Oklahoma!, "The Farmer and the Cowman".
When Milhouse stumbled upon Luann and Kirk making out during the Pox Party, he exclaims "Sweet Lizzie McGuire!"
Marge worries adult-onset chicken pox will render Homer sterile--but years of working in a nuclear power plant have already done that. However, only Mr. Burns and Smithers know this, and they covered it up to avoid paying compensation (although this is unnecessary as they already tricked Homer into signing a liability waiver in "Brother, Can You Spare Two Dimes?"). Then again, Homer asks if he's sterile in "Eight Misbehavin'", and Marge assures him he is. So either he found out at some point or she was fibbing to avoid an awkward conversation.
Milhouse (apparently) already had the chicken pox once, in "Lady Bouvier's Lover". But it is possible to contract the disease twice.
Marge threatens Bart that she will delete all his custom ringtones on his cell phone but the episode "Lost Verizon" in season 20 revealed that Bart is the only kid in his class who doesn't have a cell phone. It is possible that Bart's phone was lost, destroyed or the episode is set before "Lost Verizon".