“I didn’t stay at The Daily Show because Jon was still there and Comedy Central didn’t care about me,” Oliver told Marc Maron on his WTF podcast Thursday.
After he guest-hosted The Daily Show throughout the summer of 2013 while Stewart was directing his first feature film, Rosewater, Oliver said that they’d settled on a plan for Oliver to become the permanent summer host.
“My contract expired at the end of the year that I hosted for Jon over that summer. And I think it became clear at the end of that, that they didn't really care about me,” Oliver said, explaining that he and Stewart had a plan in which Oliver would host every summer moving forward, giving the longtime host a much needed break. “I think they could have had him for longer if they’d allowed that,” Oliver added, “but they were not interested in that at all.”
“Which is fine, but it is now painfully obvious,” he continued. “So I should probably go somewhere else.”
Oliver looked into other options (including overtures from CBS to have him replace Craig Ferguson as host of The Late Late Show), before landing at HBO. As he told Maron, “Talking to various commercial outlets, there was just an innate instinct of, I could do this, but I don’t think it’ll go great.”
Although he loved watching David Letterman mock whatever corporate conglomerate owned CBS or NBC at the time, Oliver said, “I had no standing or urge to do that. So a much easier move—the luxury move to me was to go to HBO where there is no corporate, commercial pressure from advertisers, so you truly can say what you want.”
Last Week Tonight premiered in April 2014, and returns for its 11th season on Feb. 18 with 28 Emmys and two Peabody Awards among its truckload of accolades. This year Oliver and his team won the Emmy for Outstanding Variety Scripted Series—beating out Saturday Night Live and A Black Lady Sketch Show—after the Television Academy moved them out of Outstanding Variety Talk Series, which they’d won every year from 2016-2022.
“I appreciate it because it’ll buy us—I think what it probably does for us is buy us existence,” Oliver told Maron of the show’s Emmy wins.
Over his first decade at HBO, Oliver has gained more confidence in needling his bosses, including the most recent takeover by Warner Bros. Discovery. “We’ve had three different owners in the 10 years that we’ve been there,” he said. “I don’t think we’ll be done here. It’s like, you know, new dads moving into the home. You think, do I need to learn your name? Because I reckon there’s another one coming six months behind you.”
“Yeah. And you just hope they’re not abusive,” Maron cracked.
“That’s right. And yet they all are,” Oliver replied.
Back in 2014, Stewart admitted to The Hollywood Reporter that he regretted letting Oliver go from The Daily Show, but also knew it was the right move for him at that time.
“Obviously, look, my preference would have been that I have him forever. But I also know that’s not how it works here,” Stewart said. “We get these really talented people for a certain time until other people recognize that and go, ‘Hey, why don’t I pay him more and let him do it over here?’”
So he encouraged Oliver to go to HBO: “I said, ‘You’ve got to do that. That’s too juicy a meal to pass up.’”