Jon Stewart Apr 23, 2023; New York, New York, USA; Comedian Jon Stewart during game four of the 2023 NBA playoffs at Madison Square Garden. Mandatory Credit: Wendell Cruz-USA TODAY Sports

Jon Stewart might be a big New York sports fan who frequents Mets and Knicks games, but the daily grind of talking sports on WFAN for four hours a day is a different level of commitment.

During Craig Carton’s final show on WFAN last week, he reminisced about landing at the radio station with Boomer Esiason in 2007 to replace Don Imus. Before Boomer and Carton were tasked with taking over mornings on WFAN, Geraldo Rivera, Lou Dobbs, Jim Cramer, Joe Scarborough, and Monica Crowley were among the known personalities to receive tryouts. But according to Carton, a lesser-known recruit for the gig was Jon Stewart, with CBS, which owned WFAN at the time, attempting to sell him on a move to radio.

“One of the people that CBS, at the time, wanted very badly to do the show was Jon Stewart,” Carton said. “They went to Jon Stewart to see if there would be any interest.”

In 2007, Stewart was at the height of his popularity as the host of The Daily Show on Comedy Central, which he was the face of from 1999-2015. Asking Stewart to either pull double duty or give up his nightly TV show for the daily grind of local, morning radio would seem like a tough sell unless it came with a massive pay increase.

“Imus made a lot of money,” Carton added. “So there was a lot of money to play with…Whatever money they offered Jon Stewart to do five days a week, four hours a day, Jon’s response was, ‘I make double to work one hour a day, five nights a week, and I have 20 writers! Why would I ever leave that?’ And that’s why Jon Stewart never tried out.”

According to Carton, he shared an agent with Stewart, which is why he knows CBS went to the former Daily Show host about the WFAN opening. Imus was fired by CBS in the spring of 2007, jumpstarting a furious search to find his replacement on WFAN and MSNBC throughout that summer. Scarborough eventually received the morning slot on MSNBC, with WFAN ultimately opting to deviate from politics to create a more sports-focused show.


About Brandon Contes

Brandon Contes is a staff writer for Awful Announcing and The Comeback. He previously helped carve the sports vertical for Mediaite and spent more than three years with Barrett Sports Media. Send tips/comments/complaints to