When Matthew Chestnut suddenly quits due to receiving a better job offer elsewhere, Louis is depressed that all of his noteworthy employees (except for Hector) have now left, and offers a job to Eddie. Eddie initially refuses, but when his job at the mattress store goes south, he reconsiders...only to learn that Louis has hired Trent in his place. Meanwhile, Jessica tries to become president of the Parent Teacher Association, and Emery and Evan compete to see who's the funniest member of the family.
- Awesome, but Impractical: Louis is utterly touched by a gift from Trent soon after they start working together: a personalized mug with a Western theme. However, the rim of the mug has cattle horns on it, which poke Louis (and in The Tag, Jessica) whenever they drink from it.
- Blackmail: Amy Chestnut (Matthew's wife) uses Jessica's desire to be her successor as PTA president and have power over the teachers in order to help her pack up and move, as Matthew's left town for his new job at Dollywood (in Pigeon Forge, Tennessee) ahead of his family.
- Call-Back:
- Louis' first Good-Times Montage of former employees includes a shot of "Fajita Man", aka Eddie with a fake mustache.
- The Goofy Suit mentioned below was first seen in "Working the 'Ween".
- Coordinated Clothes: While he's employed at Cattleman's, Trent wears a rancher outfit completely identical to Louis's.
- Dark Horse Victory: After spending their plot debating which one of them is funnier, Evan and Emery end up admitting that neither of them are as funny as Grandma and her Rake Take gag.
- "Dear John" Letter: Matthew ditches a Huang-Chestnut double-date at Cattleman's to leave for his job immediately, only giving his wife a letter of resignation to pass to Louis, with Louis outright referring to it as this trope.
- Green-Eyed Monster: When Louis starts treating his new employee Trent better than Eddie, Eddie gets jealous enough to get Trent fired by editing a coupon Trent had designed to offer a free steak with every soda instead of a free soda with every steak. However, after Louis becomes depressed over losing Trent, Eddie comes clean, gets Trent reemployed, and gets hired as Trent's equal.
- Good-Times Montage: Louis has two; one at the start of the episode, when he's remembering all of the employees that have left, and one after Trent leaves that focuses on just spending time with him (and causes Eddie to realize the damage he's done and confess to sabotage).
- Goofy Suit: Eddie's "promotion" at the Mattress Store is just him being forced to wear a mattress-shaped costume that some little kids mock, which leads to him reconsidering working with his dad.
- I'm Not Here to Make Friends: Jessica states this verbatim when she attends a PTA meeting, hoping to take over Mrs. Chestnut's job and become a "teacher boss", and another parent tries to greet her.
- Karma Houdini: Rather than punishing Eddie for "almost bankrupting" Cattleman's, Louis decides to make Eddie and Trent equal business partners, with Eddie working as a Cattleman delivery driver (with Grandma riding shotgun while he only has a Driver's Permit).
- Malicious Misnaming: When Jessica attends a PTA meeting to see how she can become Mrs. Chestnut's replacement as its leader, she sits besides a large woman she continuously refers to as "meatball" despite the woman's repeated statements that her name is Jamie, though it's because she brought meatballs to a potluck dinner rather than because of her body shape.
- My God, What Have I Done?: Eddie is initially ecstatic when he successfully sabotages Trent and causes him to leave, but after he notices Louis has become depressed and is starting to blame himself for driving employees away, Eddie has an immediate change of heart.
- Non-Indicative Name: Matthew Chestnut's new Dollywood job is managing a "9 To 5 Diner" that's open 24 hours, with Mrs. Chestnut stating that one of his most frequent tasks is having to explain to customers that it's always open.
- "Not So Different" Remark: Mrs. Chestnut originally just bosses Jessica around because of their mutual dislike of each other, but when Jessica decides to help comfort their son about moving away without being prompted, Mrs. Chestnut states that they're both willing to put the needs of children over themselves and she considers Jessica a worthy successor to her position in the PTA.
- No, You: When Trent calls Eddie out on being jealous he's working with his dad, Eddie retorts "You're jealous I'm working with your dad", which makes no sense in context and leads to Trent, deciding that Eddie's beyond reasoning with, just leaving instead of dealing with the chaos caused by the sabotaged coupon.
- Plagiarism in Fiction: Emery's idea of being the "funny one" in the family is copying a standup comedian's routine verbatim, including wearing a bald cap and glasses to look identical to him.
- Rake Take: When Grandma claims that she's funnier than both Evan and Emery, she proves it by leaving a rake in the middle of the living room and waiting for this to happen.
