Colin Jost's The Simpsons Cameo Makes Fun Of His Real Life Business Debacle

The Season 38 premiere of "The Simpsons" features a surprise cameo from Colin Jost of "Saturday Night Live" fame. Whereas sometimes it feels like "The Simpsons" fawns too much over its celebrity guest stars (as it did with its most-hated episode "Lisa Goes Gaga"), Jost is used more as a punching bag. His "Simpsons" alternate self shows up at Springfield Elementary to promote his children's book, which the kids don't seem to find interesting at all. The book is called "Cap'n Colin and His Fabulous Ferry," a reference to the real-life decommissioned Staten Island Ferry that Jost bought back in 2022.

Jost purchased the boat with fellow "SNL" comedian (and fellow Staten Island native) Pete Davidson, and they have both jokingly said 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 source of constant comedy on "Weekend Update," with Davidson himself once stopping by to talk about it. "We even gave the boat a new name," Davidson said. "We thought the Staten Island Ferry sounded too depressing, so now it's called the Titanic 2."

The joke with Colin Jost's "The Simpsons" cameo is that he's grown so desperate to get people to ride his ferry that he's written a kids' book to promote it. He's depicted as a man reduced to a final desperate ploy that isn't working. The appearance is hardly substantial enough to put Jost on the list of the best "The Simpsons" guest stars of all time, but it's a funny ten seconds or so if you know the story behind it. However, the gag may not be entirely accurate, as Jost's ferry purchase no longer seems like such a money pit.

In September 2026, Jost and Davidson hosted a comedy show on the ferry, a Snapple-sponsored event that went down well with those in attendance. This 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."