Episode: My Big Cups
Funniest Moment: After getting caught passing off his sons' macaroni art as his own in front of a city council meeting, Tom's beeper goes off. The Mayor, making the bizarre assumption that it's the fire alarm, begins spraying people with a fire extinguisher. "Whew, saved by the bell," Tom remarks, as the episode ends and we cut to footage of Dustin "Screech" Diamond doing a strange neck dance.
Episode: Bass Fest
Funniest Moment: The Only Married News Team are caught unprepared when their teleprompter apparently is blank. Jan is petrified while Wayne tries to encourage her. Finally, Jan asks 'Ryan' if they can cut to a commercial. Suddenly, Wayne shrieks "Ryan go to commercial!!" and you can almost tell that Tim was caught unaware by the outburst, giving the show an improvisational feel that would come to the fore with their next project.
Episode: Jeffy the Sea Serpent
Funniest Moment: No, it's not The Mayor forgetting that Tom is inside a fake sea serpent. It's the ending where the "dead" sea serpent is on display in a museum of "Nature's Greatest Mistakes", with a placard that reads "Underwater Bigfoot-Style Monstrosity."
Episode: White Collarless
Funniest Moment: Combining a poop joke with poor spelling is funny no matter how you slice it.
Episode: Wrestling
Funniest Moment: After abusing a drug to help win a boys' wrestling tournament, Tom is reduced to a wheelchair bound wreck. However, his statue is being installed next to The Mayor's, who helpfully puts a telescope in front of his "good" eye. Realizing that not only is his name misspelled, but the statue looks nothing like him, Tom moans out an exasperated cry that gets me every time I hear it.
Episode: Saxman
Funniest Moment: One of the running gags on the show was people circling things on paper like an elementary school teacher might. However, in this scene, it's combined with Tom realizing the music writing process with the creepy Saxman isn't going so well because he's working in the bass cleft.
Episode: Spray a Carpet or Rug
Funniest Moment: As the darkest episode up to this point, 'Spray a Carpet or Rug' also has an ending that is the strangest yet. After being talked into suicide, Tom goes through a surreal scene that recalls the ending of 2001 before he ends up in what appears to be heaven's version of The Mayor's office. Things quickly turn sinister before the camera cuts to The Mayor, revealed to be a demon, who screams a terrifying sound...and then the episode ends.
Episode: Surprise Party
Funniest Moment: This is one of those episodes where things get worse and worse for Tom. And while this business card/spelling joke had been done in an earlier episode (specifically in 'Re-Birth'), Tom's addition of "the phone number isn't current" is especially ridiculous since, well, the phone number is listed as "pending."
Episode: CNE
Funniest Moment: In an episode packed with hilarious things, the commercial for CNE medication takes the cake. It's first introduced as "not just your father's diaper rash medication anymore!!" and then later "though first developed as a dangerous fox repellent..." before Dr. Michael Ian Black turns it off. It's worth noting that Black holds a medical degree from Dr. Peppar's Medical Institute aka the guy behind the Re-Birthing episode's strange adoption legitimizing program.
Episode: Friendship Alliance
Funniest Moment: I have a weak spot for ridiculous products, and Rat Nap is one of the best Tim and Eric came up with. Ostensibly a liquid used to induce sleep or comas in rodents, in this episode it's used in large quantities to put Tom, The Mayor, and Gibbons to sleep for two weeks so John C. Reilly can escape town without legal consequences.
Episode: Zoo Trouble
Funniest Moment: 'Zoo Trouble' is probably my least favorite of the second season of Tom Goes To The Mayor simply because the ending is too arbitrary and silly for its own good. However, they do manage a few good laughs, such as during the ride Tom and The Mayor go on at Bernie Fusterillio's Real Live Animal Experience. Told to "smell the breath of the deadly lion", Tom's smell tube malfunctions and seals around his mouth, giving his face a coat of stinky paste as he chokes and coughs.
Episode: Layover
Funniest Moment: Fun Fact: According to the commentary, this is among Tim and Eric's personal favorite episodes of the show. While the other restaurants they came up with were funny--WW Laserz, Gulliver's buffet, Sauceman's--Fishanelli's is the best yet. A seafood establishment where you can choose your fish, dip, and waiter, the small legal text at the end of the commercial is comedy gold. You probably can't read it from an image this small, but it informs the viewer that the "squid snaplins" may contain up to 94% of a few disgusting sea creatures that clearly aren't squid. Also that color and salt have been added to maintain appearance and consumer appetite.
Episode: Couple's Therapy
Funniest Moment: During an exercise to help get some more romance into the bedroom, The Mayor is told to say something erotic without using words. He leans toward Tom and makes a series of the most strange human sounds you've heard in a long time before Gary Shandling, as the leader of the couples cruise they're on, says "Mayor, that's turning the whole boat on."
Episode: Glass Eyes
Funniest Moment: During a barrel goat hunt, the Only Married News Team are singing a song to urge the participants on. When the goats escape from Memorial Park, they begin to sing about the events unfolding. I don't know, I just think it's really funny that they quickly cut from a scripted, pre-filmed song to "breaking news" in the form of a song.
Episode: Undercover
Funniest Moment: Tom's height reduction surgery in order to pose as a child at the school was funny. So funny that Zach Galifianakis, as a doctor, laughs hysterically while describing it to Tom. However, his re-heightening is funnier still, and probably the best ending reveal of the whole series. Tottering on stick legs with an idiotically throaty voice, Tom tries to lean in toward the microphone to thank the city council before his legs snap and he falls over.
Episode: Puddins
Funniest Moment: This episode is the blackest humor Tim and Eric have ever produced. I happen to think it's among the funniest. The poem that Tom reads at his son's memorial service at the school is genius in its awkwardness, only trumped by his ensuing grief and furthering madness. Appearing at The Mayor's office, who mistakes Tom for a baboon, he tries to introduce his new son "Brindon Again." Of course it's not a real human baby: rather, it's an irritated cat, who jumps out of the empty Puddins container and crashes through a window while Tom collapses into despair. I dunno, you'd have to watch it to think it's funny.
Episode: Joy's Ex
Funniest Moment: Here we are, the last one. This episode is a fairly appropriate note to end on, especially given the psychedelic vibe the whole thing has. I mean, they do get stoned in it. Anyway, the best bit comes when Tom explains that he shouldn't go outside in the thunderstorm because his briefs have a lot of underwire. "You know, for support," he offers, striking a hilarious pose.
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