Jay Leno’s been working on this new bit about school shootings. “Let’s see if you like this one,” he says, deep into Monday’s discomfiting and fascinating episode of the WTF With Marc Maron podcast. “OK,” Maron murmurs in response, resigned, indulgent, not a little condescending. There is a half-second pause. Which can last an eternity, depending on how receptive you are to school-shooting jokes in general, but also based on how much baggage you, the listener, are bringing to this exchange; how invested you are in Leno’s history and reputation; how emphatically you intend to perform your dislike of one of the comedy world’s most performatively disliked stars.

Finally, he tells the joke. “Trump said he wants to arm the teachers. Psssss. Have they thought this through?” Beat. “Like the school librarian. Would her gun have to have a silencer?”

Maron groans softly as Leno acts out the muffled gunshots: “Like, ‘Shhhhhhh,’ puh. ‘Shhhhhhh,’ puh puh puh. ‘Shhhhhhh,’ puh.” Leno says he’s told this joke onstage a few times already. “Did that work?” Maron wonders. Did something so silly and distasteful actually get a laugh? And it will not surprise your average performative Jay Leno hater to learn that according to the man himself, it totally did.

Right up front let’s stipulate that it is not time to reconsider Jay Leno, or to “forgive” him, or to learn to truly love him, in large part because, to his credit, he’s not trying to convince you to do any of that shit. He is quite comfortable, financially and otherwise, with his notoriety, with his status as the timeless, deathless supervillain of the late-night-talk-show universe.

After, shall we say, a few regrettable false starts, Leno finally handed NBC’s The Tonight Show over to Jimmy Fallon in February 2014 and ambled off into the sunset, affable and triumphant, a lion in winter (and lots of denim). These days, he is content with a modest handful of stand-up gigs (lotta casinos) and his rhapsodically dull CNBC show Jay Leno’s Garage, which, also to his credit, makes not the slightest attempt to pander to people who do not eat, sleep, and breathe motor vehicles. “How many cars do you have now?” Maron wants to know. “Oh, man, you sound like my wife,” Leno sighs. The answer is 186 cars and 163 motorcycles.

Leno rose to supervillain status in two phases. First, he took over NBC’s The Tonight Show from Johnny Carson in 1992, beating out unsentimental cool-kid favorite David Letterman and further infuriating detractors by soundly pummeling Letterman’s competing CBS show in the ratings for the next two decades or so. Second, NBC horrifically botched Leno’s own 2009 Tonight Show handoff to Conan O’Brien, hedging by giving Leno his own hour-long 10 p.m. show to keep him from jumping to another network. When both The Jay Leno Show and Conan’s Tonight Show struggled initially, a harebrained plot was hatched to give Jay a half-hour at 11:35 p.m. and push Conan to 12:05 a.m., a humiliating demotion.

Conan quit in a huff and eventually took his talents to TBS. But not before several weeks of awkward and fully televised fury, which spread to Conan’s many defenders, including Jimmy Kimmel, the fresher-faced ABC star who lambasted Leno right there on The Jay Leno Show.

Leno: “Ever order anything off the TV?”

Kimmel: “Like NBC ordered your show off the TV?”

And so on. Kimmel’s parting shot has stuck with me: “Listen, Jay. Conan and I have children. All you have to take care of is cars. We have lives to lead here. You’ve got $800 million. For god’s sakes, leave our shows alone!”

All you have to take care of is cars. “I let that go on the air,” Leno tells Maron now, politely, adding that it wasn’t even shot live. “I could’ve edited it.” Despising Leno became a sort of Olympic sport, but he has made his peace with everything, and everyone. Even Kimmel. “He’s more like me than any other host,” Leno notes, assessing the current late-night crew. Meaning Italian. And the blue-collar background. And being, you know, a funny guy.

The whole Maron interview is spectacular. WTF superfans know that the We’re cool, right? conversations are the best, when there’s comic-centric inside baseball to discuss and personal animus to defuse. (Leno apparently booked Maron on the late-period Tonight Show solely to determine whether Maron really hated him.) As for Jay Leno superfans—are there Jay Leno superfans? Is it such a terrible thing if there aren’t?—Maron’s goal is to get his guest to express regret, to apologize, to grovel at the feet of his many haters, from Howard Stern to Conan himself. But Leno doesn’t need, or at least doesn’t want, a redemption narrative. “Who do you tackle? The guy with the ball,” he explains, affable as ever in reliving all that criticism and outright enmity. “The quarterback. And to me, The Tonight Show was the ball.” In the end, he was merely a victim of his outrageous success. And so were we.

Both of Leno’s major Tonight Show transgressions are hilarious to even contemplate now. The context is collapsing. The Conan debacle is less than a decade old but feels positively ancient: You boys were arguing about time slots? And comprehending his original sin—beating out Letterman as Carson’s successor in ’92—depends on your ability to still view the two candidates as different species. “I was the establishment guy, and Dave was the hip guy,” Leno tells Maron, still making the case for himself: He’d been guest-hosting for Carson for five years, and, unlike Letterman, was willing to travel around and schmooze with every NBC affiliate, and Letterman’s edginess made him ideal for his night-owl time slot. And really, geez, what did you want Jay to do, turn down the offer?

Meanwhile, in 2018, Letterman is the quintessential establishment guy, with a new Netflix show, My Next Guest Needs No Introduction With David Letterman, that is almost jarring in its eagerness to soothe, not so much flirting with earnest liberal-peity boredom as openly cultivating it, whether his guest is Obama or George Clooney or Malala. (These days it’s Dave getting berated on his own damn show, this time by Tina Fey.) He is apologizing, in TV-show form, for all those super-hip years of not giving a shit. This guy was a bad boy? The sad-eyed fella with the Old Testament beard who mostly wants to hear about your charity work? Really?

It’s true enough that Leno was, to put it mildly, the less threatening post-Carson option. The hater’s shorthand is that Jay was a great comedian, a mediocre talk-show host, and, per all the backroom schmoozing and scheming, a lousy human. Revisiting some of his old stand-up, Leno’s appeal is indeed enormous. It’s less any one joke he tells than his winsome, apolitical, utterly nonthreatening manner: the national-monument chin, the twinkly and parody-ready voice, the gentle everyman wit. At worst, he’ll inspire the most pleasant yawn you’ve ever yawned.

He was the safe choice, and the right choice, which made that choice no less maddening. “For me, being a Dave guy but loving Jay as a comedian, I thought Dave deserved The Tonight Show,” Maron explains in his pre-interview intro. “And Jay took The Tonight Show, and what was once a classy—though schmaltzy—outlet or show, he made it into a circus.” Sound familiar?

If you remember one concrete thing about Leno’s Tonight Show beyond its ratings dominance, it’s “Jaywalking,” the recurring bit where he’d do man-on-the-street interviews to illustrate just how little the average American knew about civics, and the government, and, well, America. It was awfully genial for something so fundamentally mean-spirited. Talking to Maron, Leno describes his style of humor like this: “It’s what you call evergreen topical. ’Cause most people don’t know anything. I learned on The Tonight Show, once you get past secretary of state, nobody has any idea who you’re talking about. They just don’t know anything. So you have to talk about, How ’bout the ECONOMY? And CONGRESS?”

This, too, is hard to square with the talk-show landscape in 2018, when we’re all political-science experts whether we like it or not, and the Trump administration’s every cabinet member and bit player gets their own personalized dunk tank. (I seize up even imagining Leno saying the name Scaramucci.) Leno was apolitical before being apolitical was uncool, or at least, he was apolitical before being apolitical could get you canceled. (In the social media sense, not the ratings sense—for a while there, Fallon had his own maddening Leno-style streak of total ratings dominance.)

Leno is, technically, still a part of the modern landscape, but Jay Leno’s Garage is defiantly dry and gearhead-centric, with nothing whatsoever to offer those with no emotional investment in the 1992 Mazda Autozam AZ-1. But as Leno chats up a clearly uncomfortable fellow car enthusiast at exhaustive length, he seems to be enjoying himself, at least, and this counts for more than you think, or at least he thinks it does.

“How does it differ from the other guy’s car show?” Maron wants to know. The difference is that in Jerry Seinfeld’s Netflix jam, Comedians in Cars Getting Coffee, the car aspect is just a gimmick, whereas its true aim is to allow Seinfeld to air his super-grouchy philosophies on where modern comedy has gone wrong. Just tell jokes! No long-winded personal stories!

Give Leno credit for being a little more open-minded. Twice in his WTF interview, unprompted, he grouses about the dour self-hatred that permeates the fictional Showtime stand-up dramedy I’m Dying Up Here, and by contrast heaps praise on a young person who, in his view, has got it right.

“To me there’s nothin’ like bein’ a stand-up,” Leno says. “When I watch Michelle Wolf, I love the fact that she loves to perform. I can tell she can’t wait to write a joke and tell a joke. There’s such an enthusiasm.” Also: no self-hatred whatsoever. “Just the fact that she revels in being a comedian. She’s so anxious to get out there. She’s like an athlete. She runs out and she punches those jokes. And some work and some don’t, like all of us do. But she really enjoys it. I don’t see a lot of angst.”

It’s true that I would’ve Venmo’d $10 to Maron on the spot to hear him and Leno discuss Nanette for five full minutes, and I would’ve preemptively cringed all the way through it. Leno was not a revolutionary figure in 1992, and he’s not about to become one now. But his notion of comedy as pure joy—no neurosis, no ruffled feathers, no political subtext—is now unexpectedly radical, even if you emphatically reject it. It is most definitely not the future. But it’s a useful prism through which to view his own troubled past. Leno seems to have few regrets about Letterman, and even fewer about Conan’s ultimate decision to quit: “To me, when you’re on, you’re winning,” is how he summarizes his TV philosophy. Leno is still on. You are almost certainly not watching. But he never needed anybody, even when he had everybody.