Thomas Pynchon and James Caan guest voice as themselves as Marge won't let a little thing like "not cheating" prevent her from winning a baking contest; Bart takes up a "swinging bachelor" lifestyle after finding Homer's discarded "Playdude" magazines.
Kim Cattrall (Sex and the City) guest voices as one of Marge's high school friends who is now a famous newscaster, leading Marge to wonder (yet again) if putting her own plans aside to marry Homer was such a good idea.
When Bart loses his last baby tooth, his solution to his "ten-year-old's midlife crisis" is to start writing slogans on T-shirts, and soon he's a gag T-shirt salesman, much to the dismay of Homer, who thinks that with Bart bringing in income, Homer is no longer needed.
NFL star Tom Brady, NBA stars Yao Ming and LeBron James, and figure skater Michelle Kwan guest voice as themselves when victory celebration choreographer Homer (who was spotted doing a dance at a local carnival) is asked to choreograph the Super Bowl halftime show, and he seeks Ned's help.
When Patty and her new lover, a female tennis professional, want to get married now that same-sex marriage is legal in Springfield, they don't have to look far to find someone to perform the ceremony - Homer, who obtained a license to perform weddings.
Selma realizes she's missed her opportunity to give birth after watching a video about menopause (with Robert Wagner). As an alternative, she considers adopting a baby from China, but she's missing one requirement: a husband. Selma is so desperate, she has Homer pose as her husband. The scheme seems to work perfectly, until a bureaucrat, Madam Yu (Lucy Liu), finds out and takes the couple's child away.
After Homer suffers a garage-door-to-the-throat incident, Marge is pressured into buying life insurance for the entire family. Much to her surprise, she finds out that Homer is uninsurable and resorts to cutting costs across the board in the household. Homer is convinced by his buddies that Marge is trying to make all financial decisions, so in an act of defiance, he buys an RV. This reckless act infuriates Marge, causing a divide between the two and ultimately forcing Homer to live in his new RV. Determined to save their feuding parents, Bart and Lisa steal the RV in hopes of returning it for a refund, but are instantly faced with obstacles.
In an attempt to prove to Shelbyville that Springfield is not a hick town, Marge convinces the town to fund a new concert hall, designed by architect Frank Gehry (who voices himself). However, Springfieldians just aren't interested, and Mr. Burns buys the bankrupt concert hall in order to turn it into a new federal prison, in which Homer is imprisoned after a snafu. Homer runs into quick trouble in prison when Fat Tony (Joe Mantegna) targets him for squealing. Charles Napier also guest stars.
When Professor Frink uses an astrology machine to ease the constant bickering between Bart and Lisa, they are given a sneak-peek into their final days of high school. In this future view, Marge and Homer are separated, Lisa is dating a muscular Milhouse and Bart is dating the girl of his dreams, Jenda, guest-voiced by Amy Poehler. Much to their disappointment, both the relationships quickly flounder. In hopes of winning Jenda back, Bart takes a job at a Kwik-E-Mart, where he becomes the local hero after saving Mr. Burns from a robber. His reward is a scholarship to Yale that was initially intended for Lisa. Bart's deeper look into the future causes him to have a change of heart, ultimately affecting his present-day sibling rivalry for the better.
This was the 350th episode of The Simpsons to air.
A storm hits Springfield, causing the Simpson roof to leak. Unable to keep a roof over his family's head, a downtrodden Homer seeks companionship at a bar called Knockers. There, he befriends a beer-loving roofer, Ray (guest voice Ray Romano), who agrees to help Homer with the repairs. When Homer's new best friend never shows up, Marge and Dr. Hibbert conclude that he's a figment of Homer's imagination and place Homer in a mental hospital. But Homer and Ray may have the last laugh.
FOX has advertised this as the 350th episode of The Simpsons, even though that title rightfully belongs to "Future-Drama."
Bart becomes addicted to fatty foods when a new vending machine is installed at the school. When he finds himself with a significant weight gain and an unconquerable food addiction, Marge and Homer send him off to "Serenity Ranch: A Forced Starvation Facility," run by Tab Spangler (Albert Brooks, in his first guest star role since Season 8), a former food addict himself. Meanwhile, Marge and Homer turn their house into a hostel to offset the costs of sending Bart to fat camp.
Lisa agrees to participate in a Krusty-sponsored "Li'l Starmaker" competition, but panics when another contestant (guest voice Fantasia Barrino) performs a better rendition of "Mockingbird." Thankfully, Homer saves the day by hammering out a manipulative tune about Springfield that leads Lisa to victory. With a win under his belt, Homer becomes a star-crazed stage father/manager, ultimately driving Lisa to fire him. A distraught Homer counters by taking another of Lisa's rivals under his wing to groom him for the finals.
An apocalyptic movie followed by three real-life omens cause a fearful Homer to research the rapture. Believing that he has deduced when the event will happen, he begins warning others as a way to secure his spot in heaven. After a skeptical Kent Brockman reports on Homer's prediction of stars falling from the sky, there's a Krusty Special blimp accident, and Homer attracts a slew of new believers. When the rapture never comes, a discredited Homer discovers an error in his calculations and returns to the Springfield Mesa alone, where he experiences a conversation with God.
Financial trouble inspires Ned to rent his rumpus room to a pair of college-aged women, who end up running a soft-core webcam from the Flanders' home without their knowledge. When Ned becomes the laughingstock of Springfield and moves his family away to a new town, "Humble, PA - Home of the Humble Figurines," an unruly neighbor moves in next door to the Simpsons, forcing Homer to beg for Flanders' return. Jason Bateman guest stars as himself.
"The Father, The Son And The Holy Guest Star" (GABF09)
After Bart is falsely blamed and then expelled for a mishap at the school-sponsored medieval festival, Fat Tony suggests to Marge that he enroll in a Catholic private school. After a rough introduction with a nun on his first day, Bart meets and instantly likes an Eminem-quoting priest named Father Sean, guest-voiced by Liam Neeson. Father Sean shows Bart the cooler parts of the religion through graphic stories and comic books. Bart's growing interest alarms his parents and ultimately drives Homer to visit the church. He, too, finds himself attracted to the religion after Father's offerings of beer, pancakes and games. It's up to Marge to bring her family back to their roots before it's too late.