One of Stewart's defining moments was his evisceration of Tucker Carlson on CNN's Crossfire in 2004. "The whole thing went down in history as Jon Stewart versus Tucker Carlson, with Stewart the champion by first-round knockout," says Devin Gordon. But 18 years later, Carlson has "turned hating Jon Stewart and everything he represents into a right-wing brand so powerful that even Rupert Murdoch balks at reining him in," says Gordon. "For the past six years, during one of the most torturous periods in recent American memory, Stewart was taking his victory laps and frittering away a cushy HBO deal while Carlson devoted himself to polishing his act, live on prime-time television, five days a week, for an audience far bigger than Stewart’s Daily Show ever drew." Gordon adds that Stewart just can't recapture his past greatness with Apple TV+'s The Problem with Jon Stewart. "Stewart’s specific genius on The Daily Show was layering facts and complexity into jokes, and stitching punch lines together into George Carlin–esque political riffs," says Gordon. "When Stewart was at the peak of his powers, no one could pack more ideas into 22 minutes of comedy. But something has turned. Now he’s the one who seems overwhelmed by complexity and prone to oversimplification. He’s the one who gets called out for fumbling facts, for missing the point, for being out of touch. It’s not just that Tucker Carlson has struck back with a Stewart-proof breed of sophistry. It’s not just that topical comedy doesn’t work as well as it used to. The problem with The Problem With Jon Stewart is Jon Stewart himself....The Problem with Jon Stewart is a strikingly unambitious, defiantly untimely show that confuses thrift with substance, as though spending money on anything but office furniture is a sign of intellectual unseriousness."