Barack Obama will sit down with Stephen Colbert for his first televised interview from the Obama Presidential Center in Chicago, a choice that pairs one of the most politically active late-night hosts in television history with the former president whose cause he championed for a decade.
Colbert announced the booking during his show Thursday, telling viewers the interview would air Tuesday, May 5 on "The Late Show." The Obama Foundation confirmed the event on Instagram, writing, "Couch booked. Volume up. Ready to go."
The selection of Colbert is notable but hardly surprising. The host has spent years operating less as a comedian and more as a reliable surrogate for Democratic politics, and for Obama personally. That he gets the first major interview from a center already dogged by legal challenges, cost questions, and neighborhood criticism tells you something about the kind of scrutiny the former president is willing to tolerate.
Obama has appeared multiple times on both "The Colbert Report" on Comedy Central and "The Late Show." The relationship between the two men goes well beyond standard celebrity bookings.
During a 2020 interview, Colbert told Obama he needed to "drink [him] in" because he missed seeing a real president. On another occasion, Colbert played a clip of Obama and told him, "I miss you." These are not the words of a journalist preparing to ask hard questions. They are the words of a fan.
In 2024, Colbert emceed a $26 million fundraiser for Joe Biden, Bill Clinton, and Obama at Radio City Music Hall in New York City. A photo from the March 28, 2024, event shows Biden and Clinton taking their seats as Obama shook hands with Colbert on stage. That kind of cozy relationship between Obama and his media allies has been a recurring pattern.
So when the former president needed a friendly face for the debut interview at his new center, Colbert was the obvious call. No risk. No tough follow-ups. No uncomfortable silences.
The Obama interview lands in the final weeks of "The Late Show with Stephen Colbert." CBS and parent company Paramount canceled the program, and it will leave the airwaves May 21, just sixteen days after the Obama sit-down airs.
CBS called the cancellation "purely a financial decision against a challenging backdrop in late night" and denied that the show's content played a role. The network's books suggest otherwise in spirit, if not in official statement: Fox News Digital reported that "The Late Show" was losing more than $40 million annually for CBS.
Forty million dollars a year is a steep price to pay for a nightly program that increasingly resembled a Democratic Party rally with a house band. Recent guests on Colbert's show included Sen. Elizabeth Warren, Pete Buttigieg, and John Kerry, a lineup that reads less like entertainment booking and more like a DNC donor event.
Outkick writer Ian Miller captured the sentiment bluntly on X, writing that Colbert was "going out the way he came in, absolutely refusing to do comedy and putting on the most boring, generic left wing talk show imaginable." Whether or not you share Miller's tone, the $40 million in annual losses suggest a significant chunk of the American audience agreed with his conclusion.
The center itself has been anything but a smooth civic project. Construction began in 2021, and the facility, located in Jackson Park on Chicago's South Side, is slated to open in June. But the years between groundbreaking and ribbon-cutting were marked by legal fights and financial questions that Obama's team would prefer to keep out of the spotlight.
A group called Protect Our Parks spent years in court challenging the project, arguing that the use of Jackson Park amounted to an illegal handover of public space to a private organization. That legal battle consumed time and public attention, and it raised legitimate questions about whether the center served the community or served Obama's legacy operation.
A Fox News Digital investigation found that surging public infrastructure costs needed to support the project were being funded by the public, meaning taxpayers were footing a bill they never voted on. Meanwhile, the Obama Foundation sought 100 unpaid volunteers even as its leadership drew substantial compensation.
Residents on Chicago's South Side have offered mixed reviews of the building's aesthetics. That's a polite way of saying the center hasn't won over the neighborhood it was supposed to uplift.
None of these issues, the legal challenges, the taxpayer-funded infrastructure, the compensation questions, are likely to come up in a conversation with Stephen Colbert. That's the whole point of choosing him. And it fits a broader pattern of Obama loyalists benefiting from the presidential center while the public absorbs the costs.
A serious interview from the Obama Presidential Center would ask about the public money flowing into infrastructure around the site. It would press on why a private foundation was allowed to build on parkland over the objections of local residents and a civic organization that fought the project in court for years.
It would ask what the center actually does for the South Side beyond providing a monument to a former president. It would examine whether the foundation's finances, including questions about how millions have been directed within Obama's orbit, match the lofty rhetoric about community investment.
Instead, viewers on May 5 will get a host who once told Obama "I miss you" lobbing conversation starters at a former president sitting in his own building. The Obama Foundation's Instagram caption, "Couch booked. Volume up. Ready to go", captures the tone perfectly. This is a celebration, not an examination.
Fox News host Jesse Watters addressed the end of Colbert's show and what it signals about changing attitudes toward legacy media on "Jesse Watters Primetime." The broader trend is hard to miss. Audiences have been walking away from late-night television for years, and the shows that leaned hardest into partisan politics lost the most ground.
Colbert's cancellation, wrapped in CBS's careful language about "a challenging backdrop in late night", is the market's verdict on a decade of replacing comedy with advocacy. The $40 million annual loss wasn't a mystery. It was a consequence.
There is a certain symmetry to Colbert's final weeks. The host who turned his show into a nightly tribute to Democratic politics will close out his run by interviewing the man who inspired that transformation. Obama gets a friendly platform. Colbert gets a marquee booking. Neither man faces a single uncomfortable question.
The Obama Presidential Center opens in June. The questions about its cost, its legal history, and its impact on the surrounding neighborhood will outlast any late-night segment. But those questions won't be asked on May 5. They never were going to be.
When you pick your interviewer the way you pick your donors, the conversation is over before it starts.
