Jon Stewart to Host Bill O’Reilly on ‘The Daily Show’ — Best Clips From Past Appearances (VIDEO)

Jon Stewart is reprising what he once called the “worst legacy” of The Daily Show. Former Fox News host and conservative personality Bill O’Reilly will appear as a guest on Tuesday, July 16 when Stewart returns to the desk of the Comedy Central talk show.

The former host of The O’Reilly Factor, which was one of Fox News’ most popular news programs for years, was fired from network in April 2017 after an investigation into harassment allegations against the host. He was replaced by Tucker Carlson, who has since been replaced by Jesse Watters. This 2024 return marks O’Reilly’s first appearance on The Daily Show since 2015 when Stewart left.

O’Reilly will be promoting his new book, Confronting the Presidents. The guest for Wednesday, July 17 will be Scott Galloway (NYU Stern School of Business professor, entrepreneur, podcast host, and author, promoting the book The Algebra of Wealth: A Simple Formula for Financial Security).

From 2001 to 2015, O’Reilly came on as a guest of The Daily Show 15 times. Stewart also appeared on The O’Reilly Update and had some memorable exchanges, like when Stewart defended rapper Common’s invitation to the White House (see below). In 2020, Stewart said platforming O’Reilly was “probably” the “worst legacy” of The Daily Show.

Jamie McCarthy / Getty Images for The Rumble 2012

“The question was always, ‘Why would you talk to him? Why do you have him on the show if you can’t destroy him?’ If you want to talk about the worst legacy of The Daily Show, it was probably that,” Stewart told The New York Times. “Those moments when you had a tendency, even subconsciously, to feel like, ‘We have to live up to the evisceration expectation.’ We tried not to give something more spice than it deserved, but you were aware of, say, what went viral. Resisting that gravitational force is really hard.”

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Stewart frequently appeared on Fox News programs as a guest providing contrasting perspectives to the conservative pundits. This O’Reilly reunion now comes days after The Daily Show opted to go dark instead of cover the Republican National Convention on Monday, July 15 from Milwaukee following the shooting at former President Donald Trump’s rally in Pennsylvania on July 13.

The Thursday, July 18 episode of The Daily Show, hosted by the News Team, will be live following the closing night of the Republican National Convention and will air at 11:30/10:30c with all episodes available on Paramount+ the next morning. Stewart will continue to host alongside The Daily Show’s News Team, including Ronny Chieng,  Jordan Klepper, Michael Kosta, and Desi Lydic alongside Dulcé Sloan and Lewis Black with new additions Troy Iwata, Grace Kuhlenschmidt and Josh Johnson.

Ahead of O’Reilly’s return to The Daily Show, scroll through some of the most memorable televised exchanges between him and Stewart through the years.

Jon Stewart Schools Bill O’Reilly on White Privilege

Stewart got the Fox News host to admit that race plays a factor in the everyday experiences of Black Americans, using O’Reilly’s own childhood living in a segregated neighborhood as the crux of his argument.

Jon Stewart Defends Common’s Invitation to the White House

In a 2011 episode of The O’Reilly Factor, O’Reilly was upset that First Lady Michelle Obama invited Common to the White House as it “validated” someone who “supported” the killing of cops. In reality, Common had written a song about a woman he believed was wrongly convicted of that crime. Stewart heavily pushed back on that framing, saying that O’Reilly and Fox News had a “selective” memory about artists who wrote songs about imprisoned figures, noting that O’Reilly never complained about Bono or Bob Dylan or Bruce Springsteen, who have all written songs on a similar subject, getting invitations to 1600 Pennsylvania Ave.

The Jon Stewart and Bill O’Reilly “Rumble” Debate

During the 2012 presidential election, Stewart and O’Reilly staged a live debate for charity in Washington D.C. Above are some of the highlights, including the men facing off about whether or not major news networks like NBC, CBS, and ABC are inherently “activist organizations for liberal causes. Stewart called Fox News an “autoimmune response” to those news programs.

Bill O’Reilly Calls Jon Stewart an “Elite Snob,” Stewart Calls Out Hypocrisy

In 2010, O’Reilly hosted Stewart on his show and called him an “elite snob” during their back and forth. Stewart clapped back and said O’Reilly, who grew up working class but became rich in adulthood, was pretending to be “blue collar.”

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