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Colin Jost’s Simpsons Appearance Jabs At His Own Failed Startup

A man of wit and mirth, reduced to despair, writes a children's tale to promote a ferry, yet in truth the vessel becomes a hall of laughter.

By mitch·5 min read
A man stands upon a ferry, book in hand, whilst children before him look upon him with indifference.

“The Simpsons” opened its Season 38 premiere with a surprise cameo from Colin Jost, the comedian and writer for “Saturday Night Live.” But unlike some celebrity guests who get the red carpet treatment, Jost gets the opposite. He shows up on the show as a man reduced to desperation, promoting a children’s book to sell rides on a Staten Island ferry he bought in 2022 — and the kids at Springfield Elementary aren’t buying it.

The book is called “Cap’n Colin and His Fabulous Ferry.” It’s a reference to the real ferry that Jost purchased with fellow “SNL” comedian Pete Davidson, a fellow Staten Island native. The gag is that Jost has become so desperate to get people on his ferry that he’s written a kids’ book about it. In the episode, he’s depicted as a man who has resorted to a final, desperate ploy — and it isn’t working.

Jost’s Desperate Book Tour

Jost’s “Simpsons” character shows up at Springfield Elementary to promote the book. The kids don’t seem interested at all. The joke is that he’s grown so desperate to get people to ride his ferry that he’s written a kids’ book to promote it. It’s a funny ten seconds or so if you know the story behind it.

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But the gag may not be entirely accurate. Just weeks after the episode aired, Davidson told People magazine that the ferry is turning into a successful entertainment venue — and that the purchase no longer looks like a money pit.

The Ferry That Became a Boat

Jost and Davidson bought the decommissioned Staten Island Ferry together back in 2022. They have both joked in recent years that they made a big mistake. “I saw a link and sent a deposit and now I’m stuck with a f***ing boat,” Davidson said on the “Family Trips with the Meyers Brothers” podcast, adding, “It’s kinda funny that this will be a lifelong problem for me and Colin.”

The ferry has been a constant source of comedy on “Weekend Update.” Davidson himself stopped by to talk about it. “We even gave the boat a new name,” he said. “We thought the Staten Island Ferry sounded too depressing, so now it’s called the Titanic 2.”

The name change was a joke about the original ferry’s reputation. Renaming it the Titanic 2 was meant to lighten the mood — though it didn’t exactly work.

A Comedy Show on the Boat

In September 2026, Jost and Davidson hosted a comedy show on the ferry. It was a Snapple-sponsored event, and it went down well with those in attendance. The show was part of the plan all along: They always intended to turn the ferry into an entertainment venue with comedy, music, and more.

After the successful show, Davidson raved about the event and the ferry itself to People. “We’re just happy everyone’s seeing what we saw in it when we bought it,” he said. “It’s also been fun proving people wrong.”

The success of the show suggests that the ferry is finally finding its footing as an entertainment destination. The joke on “The Simpsons” was that Jost had become so desperate to get people on the boat that he had to write a kids’ book about it. But the reality is that the ferry is becoming something quite different — a venue for comedy and music.

The Comparison Between the Gag and Reality

Element The Simpsons Episode Reality
Purpose of the ferry Promoting a children’s book Entertainment venue with comedy, music
Public reception Kids at Springfield Elementary uninterested Snapple-sponsored show went down well
Jost’s position Reduced to desperation Successful business move
Outcome Failed promotion attempt Proving people wrong

The episode presents Jost as a man who has become so desperate to get people on his boat that he has written a children’s book about it. But the reality is that the ferry is becoming something quite different — a venue for comedy and music. The episode’s portrayal of Jost as a man reduced to desperation is a joke that undersells the very thing it mocks.

What the Episode Gets Wrong

The episode is hardly substantial enough to put Jost on the list of the best “The Simpsons” guest stars of all time. But it is a funny ten seconds or so if you know the story behind it. The problem is that the joke may not be entirely accurate.

The ferry purchase no longer seems like such a money pit. Jost and Davidson have turned it into an entertainment venue, and the September 2026 show suggests the venture is paying off. The episode’s depiction of Jost as a man reduced to desperation is a joke that undersells the very thing it mocks.

The Irony of the Gag

The irony is that the episode’s joke — that Jost has become so desperate to get people on his boat that he has written a children’s book about it — is precisely the opposite of what is happening in real life. In the episode, Jost is a man reduced to desperation. In real life, the ferry is becoming a successful entertainment venue.

The episode’s portrayal of Jost as a man reduced to desperation is a joke that undersells the very thing it mocks.

Key Facts Box
– Ferry purchased in 2022
– Children’s book titled “Cap’n Colin and His Fabulous Ferry”
– Comedy show held in September 2026, sponsored by Snapple
– Davidson said: “We’re just happy everyone’s seeing what we saw in it when we bought it”

Source material: “Colin Jost's The Simpsons Cameo Makes Fun Of His Real Life Business Debacle,” TVLine.

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