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The Most Jay Cutler Thing That Jay Cutler Did on ‘Very Cavallari’: Week 8

As it turns out, Jay Cutler is a hair stylist, a liar, and an elite vacationer

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. Last year, 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. Join us once again on this Jay Journey, where we’ll be discussing his highlights and lowlights and best quotes, and handing out a weekly award for Jay Cutler’s Most Jay Cutler Moment. Let’s get started.


Jay Cutler Did a Podcast

“I started a podcast,” says Kristin’s friend Kelly, a person Very Cavallari highlights for approximately 20 percent of every episode for some unknown, godforsaken reason. There was a whole story line in Season 1 about how Kelly had a Canadian boyfriend, and in Season 2 there’s a whole story line about how Kelly now has zero boyfriends. I can’t explain this! It is a weird miscalculation about why people watch Very Cavallari! OK, rant over: Kelly actually played an important role Sunday night, because Jay Cutler was a guest on her podcast (which you can listen to in full here).

“Jay’s not doing interviews,” Kristin says, explaining the importance of this moment, “that’s just not something he’s ever really been interested in?” (As someone who has tried to interview Jay Cutler an unhealthy number of times, I can verify this statement!)

Jay Cutler comes to the podcast recording ready to go (read: ready to grocery shop at Walmart):

Screenshots via E!

He’s briefly thrown off by the fact that Kelly’s recording setup is just two stage microphones. Jay Cutler repeatedly says, “I need a headset”—a valid criticism; Kelly needs to step it up, and if you listen to the episode, you’ll hear how bad the sound is—but then he really digs in. When Kelly asks Jay Cutler what a day in the life of Jay Cutler looks like, he gives a great outline: “I’ve been working out more. Playing basketball a couple times—three times a week.” That’s the end of the breakdown. So to recap: A day in the life of Jay Cutler is about three hours of basketball in the morning and then … nothing else? And that’s on the days when he plays basketball! What happens on the off days? (Side note: How wet is Jay Cutler’s jumper?)

The thing is, Very Cavallari edited the crap out of this conversation—there are many more gems if you actually listen to the podcast. I did, because I possibly have too much time on my hands, and I’ve made a list of some highlights:

  • This quote: “I didn’t take college very seriously.”
  • This other quote, on Jay’s ideal post-retirement gig: “What can I do that’s not that taxing? Not 100 percent involved. But something that can fill a little time.”
  • This other other quote, on Jay’s prospective foray into the broadcasting world: “It’s a four-day commitment for 16 straight weeks … which didn’t fire me up.”
  • Jay Cutler binge-watched Friends From College, and also the Netflix Ted Bundy docuseries (Jay’s take on Bundy: “This guy, he was—whew!—he was a piece of work.”)

And to close, Kelly asked Jay whether he liked being a reality TV star, to which he bluntly responded, “No.” Welp! Too bad, dude! Sometimes in life we don’t choose our true paths!

Jay Cutler, Hair Stylist

“Jay cuts Camden and Jaxon’s hair; he just buzzes them,” Kristin announces in this episode. This really gets Jay’s goat (not his actual goat, though Jay does own one).

Huh?” he says incredulously.

“Do you do more to it?” Kristin responds.

Yeah,” says Jay. “It’s kinda textured up. It’s longer on the top.”

It’s refreshing to see Jay Cutler take such pride in something. Maybe this is what Jay should do for his next gig. Cutler’s Cuts would be the hottest “fades only” salon in Nashville.

Vacation Jay Cutler

As previewed last episode, this week Kristin and Jay went to, say it with me, CABOOOOOOO. And holy shit, was Jay Cutler ready to go. Look at this man’s vacation fit:

I didn’t know he had it in ’im.

Jay Cutler and Kristin also had a spa day (which is how we got this Instagram photo) in Cabo, highlighted by Jay Cutler wearing this somewhat tiny robe …

… and also Jay Cutler’s repeatedly making sex jokes in front of masseuses, telling them to leave Kristin’s chocolate massage mixture on her because, “I’ll get it off later.” What a guy.

Later, during a romantic sailing date in which Kristin pointed out the beach where Stephen Colletti skimboarded 15 years prior (real Laguna heads know), Kristin playfully asks, “If I fell in, would you save me?”

“Well, I wouldn’t jump in, like, right away,” Jay responds. This response, obviously, is way too honest, but also lines up with exactly the amount of effort I would expect Jay Cutler to put in.

The Cabo trip will continue into next week, when Kristin and Jay meet up with their friends, get extremely hammered, and presumably reenact this GIF:

Jay Cutler, Revisionist Historian

Perhaps the biggest fight of Season 2 of Very Cavallari went down when Wasted Jay Cutler (the accepted term) acted too wasted during a dinner party with Kristin’s friends. It was a pretty bad look, and Jay Cutler himself acknowledged that he had messed up. “It wasn’t my best effort,” he told Kristin afterward in his best podium voice. “I apologize, and obviously I’ll do better next time.”

But it appears Jay Cutler no longer feels this way about the event! After Kristin warns him that she doesn’t want a replay of the fight, he says that actually, that whole thing wasn’t even his fault.

“It’s your fault. You made me start drinking champagne at 10 a.m.”

[Looks at the judges table.] I’ve been told we cannot accept this defense—according to the judges, the burden of proof regarding whether Mr. Cutler was forced to consume alcohol falls onto Mr. Cutler, and he has not proved such a claim beyond a reasonable doubt.

The Most Jay Cutler Moment of the Week

Early in the episode, Kristin’s mom comes to town—she’s going to babysit the kids while Kristin and Jay go to Cabo—and she and Jay have a moment that’s actually very sweet. Most of it centers around small talk regarding Kristin’s mom’s luggage strategy, because as anyone with a significant other knows, making conversation with your partner’s parents is excruciatingly difficult.

But there’s also a nice moment when Kristin’s mom asks Jay Cutler how he’s doing post-retirement, and with Kristin so busy running a business; it seems like she genuinely cares. The interaction also leads to a classic Jay Cutlerism:

“Jay Cutler literally doing nothing with his life” is a theme that Very Cavallari dives into frequently—and let me just say: It never disappoints.

Come back next week for the second-to-last episode of the season, a.k.a. “CABOOOOOO, Part 2.” It’s dope that Very Cavallari is following the Game of Thrones strategy of saving the most dramatic stuff for the season’s penultimate episode.