Last Week Tonight host John Oliver poked fun at Senate Minority Leader Chuck Schumer (D-NY) in his latest monologue, highlighting the New York Democrat’s decadeslong reliance on a fictional couple, Joe and Eileen Bailey, as political inspiration.
In a Sunday night segment, Oliver mocked Schumer for referencing the Baileys, an imaginary middle-class couple from Long Island, as if they were real people. The pair, introduced in Schumer’s 2007 book Positively American, were meant to represent average swing voters who guided the senator’s policy decisions.
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“The Baileys have guided Chuck Schumer’s political life, which is a little weird given they don’t exist,” Oliver said.
This is insane.
— Blue Georgia (@BlueATLGeorgia) August 11, 2025
Apparently, Chuck Schumer has based his entire political strategy on an entirely fictional Long Island couple named Joe and Eileen Bailey. pic.twitter.com/9NoQZMY2sZ
According to Oliver, Schumer mentions the Baileys 265 times in his 264-page book, describing them in vivid, sometimes bizarre, detail, from their love for Kung Pao chicken, beard styles, and cancer scares to Joe’s thoughts on Sex and the City.
“That is a J.R.R. Tolkien-level of gratuitous backstory, and I don’t say that lightly,” Oliver quipped.
The Baileys were originally crafted as a way to represent the concerns of middle-class voters. Oliver questioned why such clearly invented characters were granted so much influence in shaping national policy.
In a past interview, Schumer admitted, “I have conversations with them … one of my staffers once said I had imaginary friends to the press … got me in some trouble.”
Oliver’s segment quickly went viral. Political commentators and social media users reacted to the host’s mockery with amusement and concern.
“If you don’t watch anything else today, take 7 mins & behold that Chuck Schumer has invented fictional New Yorkers named ‘the Baileys,’ developed an entire backstory for them over several years, & based his entire worldview on them. Does he belong in the Senate or an asylum?” CNN contributor Scott Jennings posted on X.
“This is quite a 7 minutes. About the Senate Minority Leader and his repeated use of fictional constituents,” Fox News Channel anchor Bret Baier said in a social media post sharing the segment.
“The Baileys taught Chuck Schumer how to grill,” one user joked, referencing Schumer’s infamous social media BBQ video.
“Thank goodness the Baileys are fictional people,” another user added. “Because Chuck Schumer has not delivered on the promises he made to them.”
Conservative blog Twitchy wrote its own snarky headline reacting to Democrats on social media ripping the senator: “The Left Is Eating Chuck Schumer and His Fictional ‘Bailey’ Family, So I Made Popcorn.”
What began as a storytelling tool has now become a punchline.
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While Schumer may have intended the Baileys to help humanize policy discussions, critics, both on the Left and Right, are now questioning why a leading Democratic figure has spent so much time discussing imaginary constituents.
“Schumer’s devotion to his imaginary friends may help explain why he and the Democratic Party have been so underwhelming in recent years,” Oliver said. “He seems to be focusing a huge amount on the Baileys from Long Island while forgetting other voters actually exist.”