When Grampa goes missing from Springfield Retirement Castle, Homer and Marge's attempts to find him uncover an untold past that includes a black singer (voiced by Anika Noni Rose) as a second wife and a job as a busboy with Marvin Hamlisch. Meanwhile, Lisa gets into online poker so she can get more money for a better education after Homer puts his injury settlement money in online gambling to fight back against corrupt banks.
Tropes:
- Amicable Exes: Rita and Abe to each other. They were married years ago, but they split up due to Abe choosing to take care of the injured Homer over traveling Europe with Rita. Years later, we see that they still love each other and neither holds any ill will towards each other.
- Artistic License – Law: An airport bartender gave a 6-year-old Homer some beer, this is illegal, even in real life.
- As Himself: Marvin Hamlisch playing a younger version of himself, in one of his last public appearances before his death in August 2012.
- Aw, Look! They Really Do Love Each Other: Bart admits Lisa still has a college fund, because he was using Sideshow Bob's avatar to play poker, so he won the pot. When Lisa asks why Bart chose to help her, he reluctantly admits he likes her and felt sorry for her, before angrily telling her to forget he said it.
- Bullying a Dragon: Bart uses Sideshow Bob's online avatar to gamble and leave negative Yelp reviews of Bob's favorite restaurants.
- Celebrity Paradox: Notable poker player Jennifer Tilly—ex-wife of Simpsons co-creator Sam Simon, who received a percentage of his payments from the show in the divorce settlement—appears As Herself in an instructional DVD Lisa watches, in which she suggests starting with your "Simpsons money" when betting. Lisa doesn't appear to notice.
- Drowning My Sorrows: After they saw Rita off, Abe took the then-preteen Homer to the airport bar and bought him a drink alongside his to ensure he wouldn't remember the incident.
- Epic Fail: Krusty's lawyer loses his case when Homer sues him despite the fact that Krusty wasn't one that could be sued over the case.
- Forgotten First Meeting: Homer forgot about Rita due to some combination of head trauma, underaged drinking and barely knowing what was going on in the first place.
- Hidden Heart of Gold: Bart gloats over having saved Lisa's "vegetarian bacon" but becomes angry when she corners him into admitting that he did it because he likes her.
- Hypocritical Humor: When Bart and Lisa lose their winnings after the website figured out they're minors, the dealer scolds them for breaking the laws against underage gambling. When they ask the dealer if the people they won that money from will get it back, the dealer logs out without answering the question.
- Jerk with a Heart of Gold:
- Bart initially played poker with Lisa’s college fund and teased her in the episode. However, when she goes overboard with her gambling, Bart’s able to win back her money to prevent her from losing it.
- Despite his other failings as a father, Abe sacrificed his relationship with his second wife, Rita, to prioritize the welfare of the young Homer. Finding this out causes Homer to cry in appreciation for the sacrifices Abe made for him when he was growing up.
- Oh, Crap!: Lisa has a big one when she sees that Sideshow Bob has beaten her full house with four of a kind, and she is about to lose her college fund.
- Rapid-Fire "No!": Lisa during her Oh, Crap! moment, seeing she is about to lose her college fund to Sideshow Bob.
- Scare 'Em Straight: Bart masquerades as Sideshow Bob on the poker site and beats Lisa in order to scare her off gambling with her college fund before she ends up losing it all for real.
- Status Quo Is God: Lisa gambles with her college fund and goes for the whole pot after racking up over $300,000, losing it all—to Bart. This would leave them with enough for Lisa's dream college and a comfortable lifestyle besides if not for the site confiscating the winnings upon learning that both Bart and Lisa are underaged.
- Stealth Pun: The day Homer and Marge forgot to visit Abe was on a blue moon.
- Take That!: To American banks. Leaving five thousand dollars in a gambling website and waging nothing is considered safer than leaving the money in American banks.
