For TV watchers of a certain age (and political interest), Jon Stewart’s 17-year tenure as the host of Comedy Central’s The Daily Show is infallible. From 1999 to 2015, he did his best to make light of all the crazy in the world, lambasting politicians of every affiliation and screaming, as much as one can on prime-time television, about the wealth of emperors who truly had no clothes. And then he yielded his throne to Trevor Noah. In 2021, however, Stewart found himself back at a news desk via Apple TV+’s similarly politically charged The Problem With Jon Stewart, something he says could never have happened without a little break. “I was toast after 17 years of doing what I was doing every day,” Stewart tells Ebro in the latest episode of The Message. “And I think in any creative endeavour you get to a certain point where you believe you're just maintaining it. You're no longer evolving it in a meaningful way. And so at that point, I didn't want to stay somewhere just because I could.” So he didn’t. Stewart went out on a high note and became as active as he could in the lives of his wife and two children. He spent time developing an animated show for HBO that never quite made it across the finish line, but had no real inclination to return to live television. “Someone asked me once, ‘Has time passed you by?’” he says. “And I was like, ‘Yeah, I'm pretty sure that's time's whole gig.’ But I found a staff that is so intellectually gifted but also creative and collaborative and enthusiastic—and I find it invigorating. Because really, all you can do is, when people say, 'Are you happy with it?' it's really, 'Are you happy with the process of making it?' And I've been very pleased with that.” Today, Stewart’s perspective and wit are as essential as they ever were, the comedian taking the most pride in the way his message is received by those he perceives to be fighting the good fight. “What I learned down in D.C. is it’s about the people in the trenches working their asses off day in and day out to get incremental changes,” Stewart says. “And if I can provide them a modicum of support, a small measure of attention, a small measure of stamina to help support them on their years-long drive, boy, [that’s] doing something real.” For his The Message playlist, Stewart compiled a collection of all-timers—James Brown, Johnny Cash, Public Enemy, Beastie Boys, Nirvana and Bad Brains, to name a few—bands that speak to their respective eras and, more than anything, opened his eyes to what great music is. “I basically did the ’70s, ’80s, ’90s and on,” Stewart says. “My ’90s era, I was working at MTV, so that's Nirvana, that's Pearl Jam—I was working at MTV when Nirvana appeared, and to hear somebody that had that punk sensibility just felt courageous. And then to be able to give it such hooks and such melody—it was the growl with harmony. And I was so taken by Nirvana and a lot of the bands of that era. Pearl Jam was one of those bands, Jane's Addiction. I mean—incredible.”