- In "Uneasy Rider," Duke tells jay to advertise a new product that he recently acquired wholesome foods (a division from Scum Co) called Savvy Indian Chewing Tobacco. Jay refuses since he notes that he has tremendous influence on children (cut to a kid putting a piece of bologna on the screen and referring to Jay as Bologna Man) until Duke reminds him that he's required to do what he wants due to his contract (I Will Do Anything You Say XOXOX. Jay Sherman). Later on, while Jay tries does his show, an Indian man appears live advertising the product. Outraged, Jay tells Duke to get someone to do his commercials. When Duke reminds him of his contract, Jay yanks it out of Duke's hands, rips up the contract, and quits on the spot. Duke is left in shock as the Indian from earlier cries a single tear after seeing the ripped up paper on the ground.
- Even sweeter, Duke relents and hires Jay back when both the advertising and his replacement (Rex Reed) bring the show down.
- In "Frankie and Ellie Get Lost," Jay discovers a Tobacco Executive recruited the Humphrey The Hippo Show to promote cigarette smoking to young children. Outraged, Jay announces he’s shutting the company down, but the executive asks "if they don’t have cigarettes, what’ll they do after they have sex?" Jay angrily calls him "a bad man," and he retaliates by saying if what he’s doing is a crime, "then lock me up." The result: Jay summons the police and has the guy’s repulsive ass hauled to jail. BOO-YAH!
Executive: I need a hug...
- Jay using his inheritance to clean up the notoriously filthy streets of New York and making the city pristine again. He also deports Kathie Lee Griffin and Regin Philbin to Los Angeles, but accidently ends up getting Rosanne in return.
- Marty performing his belly talents at the Talent Show. He closes it out by drawing the iconic scene at Iwo Jima on his tummy, and flexing it so the soldiers plant the flag!
- In "Sherman, Woman and Child," Alice’s estranged husband Cyrus, a country musician, tries to woo her back by singing to her. It initially works since that's her weakness, but suddenly Jay comes in with an accordion and sings a counter-love song, and it's so bad (intentionally), it brings her back to Earth:
Jay: (singing) Cyrus is just a virus.He wants to tie you down while you’re still young.Your potential is what’s essential.You could someday be another Connie Chung!Cyrus: (singing) Lover, without you there's no other...Jay: (singing) Given him a chance, he'll do your mother!
- The Nightmare Before Hanukkahnote , a movie spoof of The Nightmare Before Christmas. This was also created using the stop-motion technique. After seeing it, you can tell that the people working on this show really loved what they were doing. Seen in the first episode of season two, "Sherman, Woman and Child."
- According to the commentary, they were so proud of that gag that they bumped it from later in the season to the premier.
- Franklin has a rather unexpected one during "Frank and Ellie Get Lost."
Franklin: I could put you in touch with a man who could help you. A man named El Kabong.Security guard: That won't be necessary.Franklin: Oh, yes it will... (bashes the security guard with a guitar) Ka-bong!
- This. Just, this:
"Mr. Phillips, what do you say to those who claim this marriage is just an outrageous publicity stunt?""I SAY GAAAAAAAAZE INTO THE HYPNOTIC POWER OF MY EEEEEVIL EYE!!"
- Duke Phillips' Pre-School. "Built on a Dare!"
- "ALL HAIL DUKE. DUKE IS LIFE."
- After being transferred to the 6 am show, "English for Cab Drivers," Jay delivers a wonderful diatribe against the decline of Hollywood. In addition to being well-directed criticism, it's an homage to the big filibuster scene from Mr. Smith Goes to Washington.
Jay: (unshaven, bleary-eyed and rasping) Tell them you want stories about people, not a hundred million dollars of stunts and explosives. People, it's up to you. If the movie stinks, just ... don't ... go." (slumps over in a faint)
Professor: You were meant to tear apart what others poured their heart and soul into!Jay: I shall, I shall!!Professor: BE A TRUTHTELLER!Jay: I will, you pompous wind-bag!
- Also, his journey to rediscover his passion for art critique with the help of his old university professor.
- Jay confessing his love to Alice at the end of "Lady Hawke."
- Actually getting Siskel and Ebert to guest star on the show! Especially once you consider that the duo very rarely guest starred on anything that wasn't a talk show (though they did appear on Saturday Night Live in the infamous season eight premiere in 1982 when Chevy Chase had to appear live via satellite on a television after missing rehearsal for the week).
- Jay gets one in the pilot episode for putting his critical integrity above his recent Girlfriend by admitting that her performance was rather terrible in her debut movie.