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The Most Jay Cutler Thing That Jay Cutler Did on ‘Very Cavallari’: Week 3

Have you ever wondered what Jay would look like if he dressed up like Patrick Bateman from ‘American Psycho’?

Jay Cutler 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.


Here’s Jay Cutler Working With Heavy Machinery

All screenshots via E!

Just thought y’all should see this.

Was Jay Cutler Working Two Jobs?

Early on in the episode, Kristin is complaining about her employees (a weekly tradition), which leads her and Jay to reminisce about the early days of Uncommon James, when the two of them did everything. Scratch that—when Jay Cutler did everything. “I was the best employee you ever had—that’s a fact,” Jay Cutler tells Kristin. “I did it all: I was your IT guy, I was your consultant, your shipper, designer.

“I did the design for Little Jam—” Jay continues, before Kristin cuts him off and says, “We’re not using it.”

But here’s the larger question: Uncommon James was founded in 2017, and if I’m reading Wikipedia correctly, Jay Cutler was the starting quarterback for the Miami Dolphins in 2017. So, Dolphins fans, if you ever watched a game in 2017 and asked yourself, “Did this dude even study the game plan?” the answer is: No, he did not. He was shipping jewelry and helping his wife connect to the WiFi instead.

How Jay Cutler Answers a Call From His Wife

This guy has caller ID, right? And yet he bluntly says “Jay’s phone” when his wife calls him?

The Jay Cutler Quote of the Week

Jay saying, “I thought it’d be a fun little project but ... it’s not”

That feeling when you sign a one-year deal with the Dolphins.

Jay vs. the Jay She Told You Not to Worry About

Side-by-side images of Jay wearing overalls outdoors, and Jay in a shirt and Jay in a blazer indoors

Which brings us to ...

The Jay Cutler Moment of the Week

Usually this blog is a bunch of little Jay moments on the way toward the best Jay moment, but this week there’s really only one Jay moment that we must cover: For some reason, Kristin Cavallari sicced Jay Cutler on her employees.

I’ve long had reservations about Kristin’s skills as a manager. Last episode, it turned out Uncommon James was sending out 10 empty packages a week; it took Kristin months to fire her social media manager, despite the fact that she once changed the account passwords and didn’t tell anyone, and also went missing one time for multiple weeks; in this episode, Kristin rehired a store manager who had, as far as I can tell, been fired for assaulting a coworker (she ripped a phone out of someone’s hand, the story goes) and when a handful of employees got noticeably upset about this, Kristin was like, “I can’t have a bunch of babies working for me.” But this Jay thing may be her wildest move as a manager yet. Seriously, imagine you’re at work and your boss’s spouse—who is expressly NOT AN EMPLOYEE—strolls in and starts to evaluate you.

But OK, now that I’ve futilely expressed my rational concerns with a reality show, allow me to say that THIS WAS THE BEST DEVELOPMENT ON VERY CAVALLARI SO FAR.

Kristin’s exact instructions to Jay Cutler are “Go and be the Jay I know you are … the biggest asshole on the planet.” And Jay Cutler dresses the part perfectly:

Jay Cutler wearing a blazer

What is this haircut? How did he get it to be so aptly douchey? And did he shave for this look? I thought Jay Cutler was on a strict No Shave November policy all 12 months of the year. “Why did he dress up?” Reagan wonders in a confessional. “That’s not very Jay Cutler–like.” I AGREE.

Kristin also had told her friend that Jay “has everybody’s job descriptions, and he’s gonna go in and sit down with everybody individually.” So just so we’re clear, Jay is the two consultants in Office Space.

Two consultants in office space, both white men. One of them is John C. McGinley 20th Century Fox

It’s a Very Cavallari tradition to do quick cuts to Uncommon James employees reacting in horror anytime Jay Cutler walks into the office (here’s an example from a previous episode), and this week gave us a cornucopia of horrified faces:

A white woman in front of a computer monitor frowning
A girl with her hand on her chin, looking up
A woman looking up from her laptop, seemingly in horror
A woman turning around from her laptop screen, frowning

“Jay makes me feel like I’m gonna pee my pants,” one girl confesses. This girl then starts crying—Jay Cutler’s MERE PRESENCE brings a woman to tears. And then Jay Cutler laughs at her:

GIF of Jay Cutler pushing his hair behind his ear and saying, “Is she crying?”

Jesus, that hair.

A closeup of Jay’s hair

Jay Cutler spends his time at the office generally tearing everyone to shreds and telling them that what they’re doing is worthless. (Trying to put a positive spin on this later in the episode, one employee’s boyfriend says, “It’s not every day you have a Hall of Famer in the office,” which, Ehhhhhhhhhhh, I don’t know about that, dude.) When the head of shipping explains the labeling process, Jay Cutler responds, “So you just hit print?” He also lurks heavily:

Uncommon James employees gathered around in the office, with Jay peering over their shoulders

And jots a bunch of stuff on a notepad:

GIF of Jay looking up from his notes at the office

“He’s such a little bitch,” Reagan says after Jay Cutler leaves.

But the best part of this exercise may have been when Jay Cutler presented his findings to Kristin. That’s right—Jay Cutler made an org chart:

Jay Cutler and Kristin sitting next to Jay’s bulletin board org chart, with index cards

Just to zoom in on this a little more, notice that one of the cards just says “2 other girls”:

Close-up of Jay pointing to the index card reading “2 other girls” on his org chart

Jay Cutler is also a really big fan of the social team:

Jay Cutler sitting next to his org chart with a red arrow pointing toward “Social Team (Ballers)”

“You don’t wanna keep this?” Jay asks Kristin after their meeting; she walks back into the house without answering.

This was the best episode of the series so far. It’s always encouraging when the producers of Very Cavallari realize the absurd talent they have on their hands.