But the comedian had the tables turned on him by the biggest player in the media world this week.
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Winfrey, whose seemingly disembodied head loomed over the two hosts on a huge video screen, offered Stewart's fans something quite unexpected.
"We need a bit more sanity in the world," she said. "I wanted to show my support for you, Jon, and your audience, so here's what I did. I had my staff sneak into your studio with a little gift."
Oprah then told the studio audience to look under their seats, where they discovered red envelopes that contained airline tickets to Washington, D.C., so they can attend Stewart's "Rally to Restore Sanity" event taking place October 30.
"You're going to the rally!" she yelled. "Now get out there and restore some sanity."
The funnymen looked genuinely shocked as the crowd howled their approval.
Gossip website JustJared.com is also reporting that Winfrey will pay for the audience members' hotel stays.
Colbert, who is holding his "March to Keep Fear Alive" rally on the same day in D.C., did not take kindly to Oprah's siding with Stewart. He mockingly denounced her on "The Colbert Report," before offering to bring his studio audience to his rally...on the Chinatown Bus.