Jimmy Kimmel Almost Lost Late-Night Hosting Gig to Jon Stewart: ‘Sometimes It Pays to Be Cheaper’

Jimmy Kimmel may be one of the kings of late-night television, but his life could have turned out very differently.

While appearing on the Wednesday, October 22, episode of Ted Danson’s Where Everybody Knows Your Name podcast, the Cheers actor asked Kimmel, 57, about how he got his start in the industry.

“I was always looking for a little extra money,” Kimmel said of his early career. “I made no money, and I wound up on a game show called Win Ben Stein’s Money, which was on Comedy Central. That’s how it started.”

His job as a co-host on the TV game show ultimately led to Jimmy Kimmel Live!, all thanks to Michael Davies, “the same guy who hired me for Win Ben Stein’s Money.”

“He was an executive at ABC. He’s the producer of Who Wants to Be a Millionaire?, which I now host,” explained Kimmel. “He’s just a guy who recognized my talent when I was young, and he went to Lloyd Braun, who was the president of ABC at the time, and he said to Lloyd, ‘Listen I got this guy. I know you’re looking for a late-night show.’”

At the time, the network was seeking a replacement for Bill Maher’s talk show Politically Incorrect. ABC initially offered the slot to David Letterman, Kimmel said, “but he went to CBS instead.”

“They were almost about to hire Jon Stewart,” said Kimmel, explaining that he and the Daily Show host had the same manager.

But, before their manager closed the deal, Davies insisted Bruan watch a tape of Kimmel, and it eventually made its way to ABC head Bob Iger. According to Kimmel, “Iger said, ‘I think this might be the guy.’”

Even though Kimmel secured the gig, he admitted that not hiring Stewart was a mistake. “They definitely should have hired Jon,” he said. “If I’m in that position, there’s no question I would hire Jon 100 times out of a 100.”

After Kimmel finally asked Iger why they chose him over Stewart, Iger said, “You were cheaper.”

“Everybody laughed,” Kimmel admitted, “but I knew he wasn’t kidding. Sometimes it pays to be cheaper.”

Jimmy Kimmel Live! debuted in 2003, but the late-night host said he “screwed everything up” in the show’s early days. He recalled, “I think my vision of hell is being forced to watch my first year of shows. It took us a long time to figure it out.”