I walked out of Mystic Lake Casino Saturday night gnawing on new feelings of confused rage. I wasn’t entirely sure what I just witnessed. If it weren’t for the showroom’s no-smoking policy I probably would’ve been suffering from respiratory failure by the end of the night. I don’t normally chain-smoke but 20 minutes into that miserable affair, there wasn’t much I wouldn’t have done to keep my mind off of the humorless tragedy that was unfolding before me.

Jay Leno’s performance on Saturday night wasn’t a comedy show. It was an endurance test for my personal sanity; a 90-minute marathon of earth-shatteringly stupid monologue from America’s most reviled (and most watched) late night personality. And what better place for it to happen than Minnesota’s epicenter of greed and gluttony? The cavernous den of sin we call Mystic Lake Casino.

I’ll admit I had the bar set pretty low as we took our seats that night. I never liked Jay Leno. As a child I was always favored Letterman. And like so many of my fellow echo boomers, last year’s Tonight Show fracas only deepened my disdain for NBC’s double-chinned crowd pleaser (I will always love you, Coco).

But in spite of all my contempt, there was a morbid curiosity nestling inside me I felt the need to satisfy. After two decades, Leno’s become one of the industry’s most derided, albeit popular, enigma. He is the unfunny man’s funny man. The comedy world’s Stephanie Meyer. The great American paradox. It’s something that’s riddled me since my days of Pokemon and long division: How could a man so alarmingly dim-witted be the reigning king of late night comedy? 

A more optimistic part of me really did hope Leno would dispel my doubts. Maybe his nightly monologue wasn’t entirely representative of his comedic chops, I thought. Besides, he doesn’t write most of those jokes anyway.

The night kicked off with a head-scratching performance from Minnesota’s The Blenders. A four-man boy band that featured middle-aged pretty boys singing mo-town covers and even their 1997 Norweigan hit “I Am in Love with the McDonald’s Girl.” Yeah. But not even that garish spectacle could numb me up enough for the night’s impending inanity.  As I sat there, third row and center, I was truly in awe; the host of the Tonight Show in all his undeserved glory just a stone’s throw away.

If there’s anything more astonishing than Leno’s success, it’s his stamina. Say what you will about the man’s material, but he’s an incredible performer. There were no lulls. He works at a rapid-fire pace never failing to evoke laughter from the crowd. It was a set rife with tired and outdated commentary that ranged from Tim Hardaway’s homophobia to John Edward’s mistress. Like most late night humor, Leno’s material has always been centered on celebrity idiocy. It’s an angle that wouldn’t feel so lazy if he, oh I don’t know, threw in an actual joke once in a while. Instead of punctuating his commentary with an actual punch line, Leno simply recounts these absurdities, while his cackling audience eats it up like ravenous pigeons devouring morsels of bread.

“I’m so tired of these celebrity scandals,” Leno said. Which is hard to stomach given how much his material draws from them. If anything he should be yearning for more seeing that he’s still recycling old airport bathroom jokes about Larry Craig. Leno didn’t even shy away from poking at President Clinton’s playboy reputation quipping: “God bless Bill Clinton for bringing those two journalists home from North Korea. I’m sure the fact they were young, attractive Asian women had something to do with it. Hey, I don’t see him going across the world to save Helen Thomas’s ass”

He also went on to devote a good portion of his routine to railing against “Fat America”:

“You know what transfat is? I just found this out,” Leno said homing in an individual seated in the front. “It’s the fat they liposuction off of transexuals!”

Got ‘em, Jay!

I watched on with weary resignation as the late night icon bounced from one moronic punch line to another. But of course, Leno didn’t leave the stage without engaging in a little playful crowd interaction. As we neared the end of the set, I was running on fumes. I’d finished off the remainder of my coffee long ago and given up on even trying to look entertained. He sauntered the stage making each exchange more vapid and tasteless than the last. At one point, Leno even jokingly suggested that one of the (possibly shy) less talkative audience members was autistic. Don’t worry, there were still guffaws aplenty.

There’s one thing most people dont know about Jay Leno. Despite what he might represent today, his rise to stardom wasn’t simply some wonderful accident. While that time has passed, Leno was once a respected and accomplished comic in his own right.

Last year, when asked to comment on the Tonight Show’s hullaballoo, Patton Oswalt was quoted saying “Comedians who don’t like Jay Leno now, and I’m one of them, we’re not like, ‘Jay Leno sucks;’ it’s that we’re so hurt and disappointed that one of the best comedians of our generation… willfully has shut the switch off”

I’ll have to take Mr. Oswalt’s word for it seeing that I didn’t exist till 1988 and had no real concept of humor till, oh lets say… 1993. Nonetheless, the unfunny Jay Leno we see today is the one that audiences will remember. And as far as I can tell, he doesn’t seem to have any problem with that.