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The Most Jay Cutler Thing That Jay Cutler Did on ‘Very Cavallari’: Week 4

Or: The King Returns to Chicago

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.

The Jay Cutler School of Post-Retirement

The king hath returned—Thursday night’s episode of Very Cavallari saw Jay Cutler and Kristin Cavallari travel to Chicago, where, weirdly, they were not welcomed back with a parade. My theory: This episode was filmed before the NFL season began, in a time when all of Chicago had yet to comprehend the Trubisky-induced hell they were living in, and thus, how lucky they had been to have ever had Jay Cutler.

While in the Windy City, the Cutlers get dinner with former football player Zach Miller and his wife, Kristen (presumably, Jay and Zach’s friendship was forged solely on their wives having almost the same name). Miller is also retired now—if you don’t remember, he’s the former Bears tight end whose career was cut short after he injured his leg so badly that there was genuine concern that it might need to be amputated—so of course the dinner conversation turns to how both guys are spending their golden years. And once again, Jay Cutler does not have much to add.

“I’ll figure that out soon,” Jay responds when asked how he’s filling his time, as if he hasn’t been retired for more than two years at this point. Lawn-mowing and driving the kids to school are mentioned as two things Jay Cutler has picked up since retiring, but uh, those are things that most regular people with jobs also do, so they don’t exactly count as rewarding post-retirement hobbies.

“It’s just a lot of time to fill,” Jay advises Zach, “and I think some people figure it out pretty quickly and some people don’t.” It’s unclear from the way Jay says this which category he thinks he falls into. Either way, I’m really not sure Zach Miller should be taking advice from a guy who (a) once said he was trying to do the opposite of staying busy and (b) is wearing this shirt:

Jay Cutler Was a NERD

While in Chicago, Jay Cutler and Kristin also make time to stop by her mom’s house in Barrington. Kristin, you see, lived there until her early teen years, when she was sent to Laguna Beach to live with her dad because she was “getting into too much trouble” in Illinois. (Incredible “what if” to consider here: If Kristin isn’t a teenage dirtbag, she never gets sent to Laguna, never appears on MTV’s Laguna Beach, and then The Hills, never gets famous, never meets the quarterback of the Chicago Bears, they never get married, and this show never happens. What I’m saying is thank you for smoking so much pot in middle school, Kristin—this blog wouldn’t exist otherwise.)

At Kristin’s mom’s house, the trio reminisces about her rebellious years, which included sex, drugs, and literal arrests. Eventually, the conversation turns to what Jay Cutler was doing in high school, and it becomes incredibly clear that he was NOT COOL. The only time he got in trouble, he says, is when he slightly missed curfew after graduating. What a lame. Even Kristin’s mom thinks so—she spends the next few minutes dunking on what a dork he was, while he makes this face:

I Now Know How Jay Cutler’s Bracelet Works

During the Very Cavallari Christmas special, we covered the fact that Jay Cutler designed a bracelet for Uncommon James, and that it was the most confounding piece of metal I’d ever laid eyes on. “I don’t really understand how the whole half-bracelet, half-bottle-opener thing works?” I wrote. “I’ve watched the above video several (107) times, and I still can’t tell whether this piece of jewelry is just a bracelet with a gigantic bottle opener hanging off of it?” But now I know: The bracelet isn’t also a bottle opener—they are separate entities and you NEED THE BOTTLE OPENER TO PUT THE BRACELET ON.

Is this a revolutionary approach to bracelets? No. Absolutely not. It’s the dumbest thing in the world.

Just a Good Jay Cutler GIF

I considered making this the entire blog post. I probably should’ve.

Jay Cutler Gets Buckets

Early on in the episode, Kristin’s friends ask Jay Cutler whether he worked out that day. “Basketball,” he replies, articulately.

“Are you good at basketball too?” one of the friends asks.

“I’m OK,” Jay responds sheepishly.

Fast-forward to the dinner with Zach Miller, where the details get filled in a little more—apparently Jay Cutler is playing ball with the other dads at his kids’ school. At the dinner, though, Jay Cutler is far more confident about his game.

“Are you getting buckets, though?” Zach asks, to which Jay self-assuredly responds:

So what is it, Jay? Are you just OK or are you getting these buckets? Are you the Jay Cutler of basketball or are you … good at basketball?

I tried to answer these questions to the best of my ability (by Googling “Jay Cutler basketball”) and I found this video of Jay Cutler dunking:

Therefore I am compelled to conclude that yes, Jay Cutler is getting buckets.

The Most Jay Cutler Thing That Happened This Week

The Zach Miller dinner was full of good nuggets—part of the chopped-up conversation was hard to follow, but it seemed to indicate that Jay Cutler and Zach Miller once got so hammered the night before a football game that they “didn’t feel normal until midway through the third quarter”—but the best one is a story Zach and his wife tell about someone asking Jay Cutler for an autograph: “She was like, ‘It’s my mom’s 50th birthday, she’s the hugest fan of you, Jay, can you please take a picture with her?’” Kristen Miller recounts. “And Jay goes … ‘No.’”

Seeing as one of the more infamous Jay Cutler stories is the time that he yelled “DOOOOOON’T CAAAAARE!” at a man in a public bathroom, of course this is the Most Jay Cutler Thing That Happened This Week. There is nothing more Jay Cutler than this.