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The Most Jay Cutler Thing That Jay Cutler Did on ‘Very Cavallari’: Week 2

In an episode that affirms Jay Cutler as one of Chicago’s foremost sports heroes, the man himself summarizes his entire personality in one simple sentence

E!/Ringer illustration

All this time we were trying to force Jay Cutler to be a great NFL quarterback when really we should have been letting him fulfill his destiny as a perfect reality TV character. On his wife Kristin Cavallari’s reality show, Very Cavallari, we met the real Jay: animal lover, sometimes-supportive husband, man whose ultimate goal in life is to do as little as possible. It was a glorious revelation—and now he’s back. Welcome to Season 3—and welcome back to this blog, where we’ll once again go on a Jay Journey to discuss his highlights and lowlights and best quotes, and hand out an award for Jay Cutler’s Most Jay Cutler Moment of the Week.

Jay Cutler, Chicago’s Son

I don’t know whether you know this, but Chicago loves Jay Cutler. He was obviously a Windy City hero, a man who had a 51-51 record as a starter with the Bears over eight seasons and made a total of … one playoff appearance. He was a ray of sunshine before Hurricane Trubisky. He is arguably more beloved than Brian Urlacher, an eight-time Pro Bowler who merely dated an anti-vaxxer; Jay married one!

I asked my colleague and Chicago native Robert Mays how much Chicagoans adore Jay Cutler on a scale of one to Michael Jordan—he said “three,” which is apparently lower than Mark Prior levels. But this cannot be true, because Very Cavallari has revealed some extremely anecdotal evidence that seems to speak to Jay’s overwhelming popularity: Chicago is allegedly one of Uncommon James’s best-performing markets. They’re buying that jewelry like nobody’s business up there!

And why do you think that is? Do you think Midwesterners are particularly fond of, quote, “JFK Necklaces?” First of all, WHY on earth would you name a necklace after JFK? Second of all, no! Chicagoans must only be buying this stuff—and I have no proof of this, it should be said—out of an affinity for Jay Cutler. They are trying to express their love and loyalty through jewelry purchases. Frankly, it’s very touching. Some football players get statues; some get their name plastered on the facade of a stadium. But Jay Cutler? He’s sitting at home watching the Chicago-based orders for his wife’s minimalist accessories go through the roof. It’s enough to make Jim Nantz weep.

Jay Cutler vs. Gwyneth Paltrow

The whole reason Chicago came up on Very Cavallari is because, seeing all of the Cutler-related action up there, Kristin is now dead set on opening a new store in the city. (“Fun city,” is the only thing Jay Cutler says about Chicago in this episode.) But there’s one problem: Kristin wants to combine two storefronts into one massive space, and one of the storefronts has already been purchased … BY GOOP.

For the uninitiated, Goop is the Gwyneth Paltrow–owned lifestyle brand that sells everything from clothes to candles and peddles wellness in a way that is maybe destructive and almost certainly exploitative. In the past, Goop has sold such illustrious products as the “At-Home Coffee Enema” and the “This Smells Like My Vagina Candle.” But as debatably absurd as Goop may be, there’s no question that it is the blueprint for celebrity-driven lifestyle brands. It is patient zero for famous people hawking merch with zero authority beyond “being famous,” and therefore it is basically directly responsible for Kristin Cavallari’s Uncommon James. So it’s just very funny that both brands are vying for the same real estate in Chicago. (It’s also very funny that Goop is mentioned by name only once in this episode; every other time it’s merely referred to as “somebody” or “the people next door,” as if Kristin Cavallari isn’t about to go to war with the Original and More Elite Kristin Cavallari.)

But it all ends on a happy note, as by the end of the episode Goop has willingly (?) vacated the space. I’m a little skeptical about how all of this went down—I just don’t see a world in which Goop cedes ground to Uncommon James, nor a world in which Cavallari has enough money to buy out Gwyneth Paltrow. The only explanation is that Jay Cutler stepped in and threatened to use the immense good will he’s built up in Chicago to drive Gwyneth Paltrow out of town. It’s his city—if anyone’s selling a thing that helps you shoot coffee up your butt, you better believe it’s gonna be him.

Jay Cutler’s Greatest Fears

Over lunch at one of Nashville’s many hot chicken joints, Jay Cutler summarizes his personality as efficiently as possible:

What an incredible statement. What a window into Jay Cutler’s soul. Asked to elaborate, he explains that the last scary movie he saw was Scream, a film that was released in 1996. He then goes no further—he does not tell us the last time he ate a chicken tender that was not sufficiently spiced. I bet it was more recent than he’s seen a horror movie, though—something tells me he’s more willing to budge on mild nugs than he is on watching Midsommar.

The Most Jay Cutler Moment of the Week

“What’s up?” Kristin asks Jay Cutler upon arriving home.

“Mowing,” he responds, notably not wearing shoes.

But then the camera pans out, and you see the machine Jay Cutler was operating:

This is not a lawnmower—this is a fucking character from Transformers. Jay Cutler was not merely “mowing”—he was starting a lawn care company that will have only one client: himself.

Buying the largest possible machine for an extremely simple yet manly job is just a very classic Jay Cutler move. It speaks to Jay’s dadness, his dudeness, and his supreme dream of doing absolutely nothing except taking care of his yard (a Very Dad Dream, by the way). But it also speaks to the fact that Jay Cutler has more than $100 million to blow through, and that he will do it in the most unnecessary ways. This tractor—which is taller than Jay Cutler’s wife and, outside of this instance, is probably only ever operated by contract landscapers—is Jay Cutler in a nutshell.