The Reinvention of Jay Cutler: How the Enigmatic NFL Quarterback Transformed Into One of Reality TV’s Most Beloved Characters


Since retiring from football, more or less for good, Jay Cutler has found himself with some time on his hands. 

As Very Cavallari fans well know, he’s filled many of those hours convincing wife Kristin Cavallari to move to their new 10-acre farm in the Nashville suburb of Franklin, Tenn., complaining about the employees that make up her Uncommon James jewelry and lifestyle brand and, yes, monitoring the deer cam for sightings of his least favorite buck Dale. But he also found a moment to flip through a 2017 issue of GQ. In there, as Kristin relayed to a pal on an episode of her reality show last season, he came across an article that helped him brush up on his bedroom skills. 

“The sex is the best it’s ever been,” she giddily revealed after her pal inquired about their five-year marriage. Asked for more details on the particular piece (ahem, those that are curious can find it here), she replied simply, “I don’t know, but it’s been a game changer.” 

Sure, Jay went 74 for 153 in his NFL career, but these days? These days all he does is win. Very Cavallari, as the name suggests, was meant to serve as Kristin’s star vehicle, trumpeting her return to reality TV more than eight years after she walked away from The Hills and Laguna Beach. And while KCav is refreshing and authentic in this most honest look at her real life—and every bit as fun as when she was living it up as an L.A. 20something—there’s no denying Jay is the true breakout star of the series, returning to E! for season two tonight at 10 p.m. (Even Kristin freely admits it telling E! News, “He’s comin’ for me!”)

Twitter users, some of the same people who crucified the Vanderbilt alum, 35, for every errant pass he slung as a quarterback first for Denver, then Chicago and finally Miami, are simply living for his dry wit and unflappable personality. 

And, to be honest, he’s not trying all that hard. Which is pretty much the point. 

He need only share his desire, for instance, to get the hook up on a Nigerian dwarf goat purveyor, describe his vasectomy to pals or give his thoughts on what it takes to raise chickens (“Feed ’em, water ’em…it can’t be that hard. It’s got to be easier than raising kids,”) and fans flood social media begging for more Jay, dubbing him as one viewer said “arguably the best reality TV star of all time.” (Sports and pop culture website The Ringer even had a regular “The Most Jay Cutler Thing that Jay Cutler Did on Very Cavallari” column to celebrate the first season. Nominations include the time he caught a kitchen towel on fire and his failed attempts to catch a chicken.) 

As for Kristin, 32, she remains unbothered by her husband’s scene-stealing. “He’s had this image, playing football and everything and now it’s nice for people to see the real side of Jay,” she told E! News.

This was precisely the type of payoff the True Roots cookbook author was hoping for after watching sports devotees trash her man for the better part of a decade. “It’s all been very positive,” she told Mario Lopez on his radio show On With Mario Lopez last July. “It’s even stuff where, you know, these sports fans in particular are watching and going, ‘I really wanted to hate him, but he’s really funny.’ And, obviously, I mean, I’ve known Jay, we’ve been together for eight years, I’ve known that he’s always been very funny. But I love now that other people are getting to see that side of him.”

And to think they almost missed out. 

Filming their three kids Camden, 6, Jaxon, 4, and Saylor, 3, was always a non-starter. “We want them to make the decision when they’re old enough to have their lives plastered everywhere,” Kristin explained to Paper. And since the family settled down into their forever spot in Nashville, they’ve been able to give their brood the most normal of existences. “Like, my kids go to public school, and they take the bus home, and, like, they’re outside playing with the animals,” she recently shared with E! News ahead of the second season premiere. “Like, that’s all just really awesome for us.”

But in an effort to show a touch of her personal life, she worked to bring the athlete on board. 

“Jay is honestly probably the most private person you’ll ever meet, so that was a bit of a challenge,” she admitted to Lopez. “And I think, too, for him obviously he’s heard some of my stories about Laguna Beach and The Hills, so he had a lot of reservations.” 

Plus, signing on to a reality show went against the retired footballer’s newfound raison d’être. As he explained to his bride, “I’m not looking to do a lot of work right now. I’m looking to do the exact opposite of that.” 

Still, the reality star can be awfully convincing. Or, as she put it to E! News, “Well, happy wife, happy life, let’s be honest. He didn’t really have a choice. You’re doing this reality show, Jay.” 

So, as he relayed to Chicago’s ESPN radio station WMVP-AM 1000, he committed to the lightest schedule possible. “I told Kristin that I just kind of want to be…five minutes here, five minutes there. But don’t expect a lot from me. At all.” Agreed Kristin, “He would be like, ’10 minutes, we’re done, we got it.’ Take his microphone off.”

Little by little though, he began creeping into more episodes, he told WMVP-AM 1000: “Apparently it’s blown up a little bit more than we anticipated.” 

And thank god for that. Because viewers could have been deprived of countless Jay witticisms. Take this tableau from the show’s premiere when Kristin asked her newly retired husband what’s “on tap” for him that day:

“I’ve got a big 2:30 appointment—getting the boys from school,” Jay noted. “Want to be first in line, beat all the other moms there.”

Unimpressed, Kristin replied, “But, like, honestly, what do you do all day?”

His response: “I like to keep myself pretty free so if something does pop up, I can bounce right into it.”

Or there was the time a sympathy-seeking Kristin calling Jay from her employees’ Florida retreat to complain about her hangover. 

“I can’t do it like I used to. I feel awful,” she started. “I hate alcohol. I literally was drinking like I was 21 again.”

“Well man,” Jay replied. “That’s kind of how it goes.” 

Eager to talk to someone perhaps a little more empathetic, Kristin asked about the children. 

“One’s at school,” he said. “One’s sleeping. I don’t know where the other one is at.”

When Kristen asked if he could locate the missing child and have them on the call, he replied drily, “Uh. I don’t know if it’s really good for them to see you like this.”

The success is in his irreverent delivery. But also the simplicity. 

Jay, unlike countless reality stars that have come before, isn’t trying to get attention. He’s not picking fights to earn screen time or creating a narrative to remain relevant. He’s simply going about his day. In a post-football world, that could mean test-driving Luke Bryan’s llama to see if the animal could fit in with the 30 odd chickens and goats they have at their spread or chiming in when Kristin’s pal Kelly Henderson shares her dating woes. Or, it could mean not really doing anything at all. As he said on air, “It’s kind of fun sometimes.” If viewers are into it, that’s cool. If they’re not, he’s fine with that too. 

“That’s Jay,” Kristin told E! News of the comfortable, teasing banter viewers are relating to. “He does not play anything up.”

For Jay, it’s the same blasé attitude that tended to get him in trouble on the gridiron. The one that gives fuel to an urban legend about the quarterback being approached by a Vandy alum as he stood at a urinal. The guy told him he was certain they knew some of the same people and was eager to compare notes, but, as the tale goes, Jay wasn’t into it, simply leaning back and bellowing, “Dooooooonnnnnntttt caaaaarrre!” 

But those close to him swear he’s not indifferent when it comes to his career, just misunderstood. Obviously he cared about winning, about earning his multi-million-dollar paycheck. But he wasn’t going to bother himself with worrying about what haters thought of him as he went about the business of doing his damn job. 

“I’ll say this: There was never a time when we were on the field that Jay didn’t take his job 100 percent seriously,” former Vanderbilt wide receiver George Smith III insisted to Bleacher Report last year. “Never.” 

Echoed onetime Chicago Bears defensive end Corey Wootton, “He’s like, ‘Hey, I’m getting paid to do what I love. I couldn’t care less what you people are thinking.’ If more people thought that, we wouldn’t see as many Twitter back-and-forths between players and fans. You have to respect that.” 

With those in his inner circle, “He is one of the most loyal friends you’ll ever have,” Bears tight end Zach Miller told Bleacher Report. “Once you get to know the real Jay, he’d give you the shirt off his back….I love the dude. It’s not even his jokes—it’s his demeanor. He can say something straight-faced and everyone knows he’s taking a dig at you. You’ve got to be around him to really appreciate the real Jay Cutler.”

That guy, someone fans got their first true glimpse of on Very Cavallari is, indeed, quite hilarious. He’s also tough as they come and secure enough not to care in the slightest about how others perceive him.  

When Kristin took to social media celebrating the show’s season two renewal, Jay maintained his street cred. “Hard pass,” he replied as his wife asked him to share his excitement. 

But behind the scenes, yeah, he’s thought about his second act. It started shortly after the premiere when friends started calling to congratulate him on a successful debut and mentioned his tendency to outshine his more gregarious bride. “We were cracking some jokes,” he admitted. “We were just going to call it Barely Cavallari.” 

And since he’s got some time on his hands —aside from fixing up their new eight-bedroom spread and spending Halloween with the kids for the first time, Cavallari tweets that his post-football career is “still TBD”—he’s floated a few ideas for their sophomore season.  

Kristin is still undoubtedly running the show as she juggles the 70 employees associated with her Uncommon James brand, her new baby Little James (“It’s the only thing I’m doing that my kids care about, so that’s exciting,” she tells E! News of the children’s clothing line) and her family.

And she maintains her authenticity throughout. Take the season two teaser confession that she and husband of nearly six years “are in a serious funk,” as they adjusted to their changing roles in the relationship. 

“Marriage on the rocks, you guys!” she joked to E! News’ Giuliana Rancic and Jason Kennedy. “No, you know what, honestly, I mean, it was important for me to be honest about what we’re going through. Marriage is hard. I mean, anyone who’s married knows that its ups and downs. And, you know, once Jay retired from football, my career really took off. So we’ve done a complete 180. We’ve completely shifted roles. And so it’s just navigating this new normal for us.”

That includes Cutler’s new status as reality superstar. “It’s funny because now all of a sudden that he’s getting a very positive reaction, he’s all in,” Kristin detailed to Lopez. “He’s like, ‘All right, so for season two…” and I’m like, ‘Oh really? Get out of here!’ Funny how the tides have turned.” 

Indeed, the times have changed. These days Cutler mainly plays to a crowd of four at home, rather than a stadium of screaming fans. (Plus the roughly 700,000 that have tuned into Very Cavallari’s inaugural season.) But he’s definitely bringing his A-game.

Very Cavallari returns Sunday, Mar. 3 at 10 p.m., only on E!





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