A Plot: Barry is resistant when Geoff, Andy, and Rob want to induct the school's resident "Deadhead" (fan of The Grateful Dead), Matt Bradley, into the JTP. He tries to make it as hard as possible for Matt to pass the "initiation tests", but Matt does anyway. With Barry out-voted 4 to 3 (as leader; Barry's vote counts as three) the JTP goes to the Grateful Dead concert instead of the Fat Boys, which Barry wanted. Barry then tries to get the group kicked out of the concert, but to no avail. The other JTP members chastise Barry for being selfish, causing him to quit and try to start a different posse. When the member recruitments are a disaster, Barry apologizes and asks to be back in the JTP. (The closing sequence mentions that Matt Bradley wound up being Barry's best friend after high school and becoming the fifth member of the JTP.)
B Plot: At home, Adam yells out the F-bomb when Pops knocks over his video camera, and Beverly hears it. Beverly starts a "swear jar" that any family member must donate to if they use a curse word. Erica laughs at this, as Beverly is the worst offender in the family, and proclaims they'll soon have enough of Mom's money in the jar for a trip to The Bahamas. Erica even finds a way to get Murray to donate whenever he calls one of his kids a "moron" because it is hurtful. Beverly insists that any money be used for a trip to Colonial Williamsburg, which Erica and Adam strongly oppose. As Mom and Dad put in more money, they try to even things up by creating a "Baditude" jar for any time Erica says something sarcastic and condescending, plus an "Adam" jar for whenever Adam says something nerdy or refers to a science fiction movie. All-out "jar wars" ensue, and money starts going from jar to jar. Realizing they can't do anything other than be themselves, the group ceases the jar wars, while Erica and Adam relent and agree that another trip to Colonial Williamsburg won't be so bad.
- Batman Gambit: Inspired by an episode of What's Happening!! when Rerun tries to bootleg a Doobie Brothers concert, Barry brings several cassette recorders to the Grateful Dead concert to get himself and the JTP kicked out. Unfortunately for Barry, he learned that the Grateful Dead allow their fans to bootleg their concerts, and when he admitted to his plan, the JTP calls him out for this, and Barry gets kicked out the group.
- Hypocritical Humor: Bev is furious at Adam for using the F-word, but as Erica points out, she uses the same word on a regular basis.
- Irony: Barry tries to get Matt Bradley to leave the JTP by embarrassing him at a Grateful Dead concert. His method of embarrassing him involves being caught recording the concert, inspired by a similar plot on What's Happening!!. However, The Dead are one of the artists that encourage this and the move ends up getting Barry ejected instead.
- Loophole Abuse: Twice. Erica thinks to get Murray to put money in the swear jar for his constant use of the word "moron" (claiming it feels like a swear), but he just decides to put $20 in the jar so he can say the word as long as he wants. For that many freebies, Erica instead demands he put in $50, and he declares it's Worth It.
- Moving the Goalposts: Barry had Matt perform several impossible tasks to in order for him to join the JTP. To Barry's shock, Matt managed to complete them.
- One Judge to Rule Them All: During the JTP's group votes, Barry has three votes due to him being leader, while the rest only has one vote. As a result, most of the votes end in a tie, but with Matt joining, Barry gets outvoted 4-3, and the result of it was that the JTP goes to a Grateful Dead concert instead of Barry's choice, The Fat Boys.
- Shout-Out: Adam shouts "OHHHH... FUDGE!", just like Ralphie in A Christmas Story.
- Start My Own: After getting kicked out of the JTP, Barry tries to start a new posse, but can't find any good candidates and eventually begs to be let back in.
- The Swear Jar: Beverly tries to set one up, but she ends up putting the most money in it, and things quickly spiral out of control.
