I can still remember where I was the first time I watched an episode (or, more accurately, a clip) of The Daily Show With Jon Stewart. I was 14 or 15 years old and seated cross-legged on my bed, attempting the grown woman’s task of plucking my own eyebrows, when a segment in which Stewart hilariously excoriated John McCain’s 2008 presidential campaign came on. I watched the whole thing rapt, like a good ninth-grade liberal, then made my way to the Comedy Central website to watch more or less everything Stewart and his “best f*cking news team ever” had ever recorded.
Even as a weird, comedy-obsessed kid who should arguably have been socializing with her peers rather than observing a middle-aged man inveigh against media hypocrisy, I could tell that Stewart was special. He was always prepared with the kind of riposte I wished I’d had ready when someone in class said something snotty, and while I now know a team of writers was behind his signature opening monologue, I still thought of him as something resembling God (if God wore a series of silly little suits). Despite all this adulation, though, I don’t remember ever being crushed out on Stewart. Granted, I was (a) a closeted lesbian at the time and (b) maybe associating him too closely with my dad (another acerbic, elegantly graying middle-aged Jew), but now that Stewart is back hosting the Daily Show on Mondays and thirst for him has erupted from all corners of the internet, I can’t help feeling like I’m out of step.
I can objectively see Stewart’s appeal in 2024 (I mean, the man looks good for 61; righteous anger seems to work wonders for the skin), but for a more fleshed-out explanation of why he’s captured the heart of so many, I turned to my friend Sophie Strauss, a stylist living in Los Angeles. “There was something very sexy and quite literal-daddy about watching somebody make sense of a confusing world when we were growing up, and do it in a way that was funny,” Strauss says. “I think the other thing about Jon Stewart versus somebody like Stephen Colbert is, he was never afraid to be caught being really sincere and genuine about the things that he felt strongly about. That was rare, especially at that time; maybe it’s more common now, but he was really unafraid of being emotional and getting heated about stuff, and I think that was sexy.” Another friend, whom I’m not naming due to the bawdy nature of her comment, describes her level of attraction to Stewart simply: “I would climb over his desk.”
“Something about [Stewart] reminds me of a simpler time,” says Leslie Martin, a political analyst living in Washington, D.C. Indeed, I think this scrim of nostalgia is key to his allure. Despite the fact that he’s possibly hotter now than he was in 2008, Stewart inarguably reached peak cultural saturation in the early-to-mid-aughts. While the world was—let’s not fool ourselves—still plenty bad back then, in the wake of a Trump presidency and on (gulp) the possible brink of another one, it’s almost soothing to recall the days when Sarah Palin being called “Caribou Barbie” became a full-blown political scandal. The year 2008 was when American politics made an official shift from the bizarre to the uncanny—remember all the Barack Obama Photoshop bullshit?—and Stewart was the perfect, well, steward through all the insanity. That his recent return to the pop-cultural milieu feels genuinely welcome, and not forced or cheesy, is pretty remarkable. (But this could also be, at least in part, because he’s one of the only cis, straight men of his status willing to speak out about issues like the rise of anti-trans legislation.)
If present-day Stewart still doesn’t really do it for me, I have to admit that the figure he cut as a young, handsome, Jewfro-sporting William Mary student and soccer player was exactly to my taste when I was a teenager. He’s the kind of guy I would have hoped could look past my silent, classmate-avoiding exterior and noticed the Borscht Belt heart and Oh, Hello–fan soul beating beneath my off-brand polo shirts. As an adult, though, I’m mostly just grateful to have Stewart back at his desk. He’s been married for the last 24 years, but I hope knowing that legions of weird, youngish women still consider him a stone-cold hottie puts some spring in his step. (Actually, does he even know about this? I can’t really imagine him searching his own name on social media—which is yet another feather in his sexy cap.)
