The real story behind the Jay Cutler beer-chugging video on Bridge Street in Vail
‘Are you done with those beers?’
Jack Bossong, 25, calls Jay Cutler “the coolest human of all time” in his latest episode of “The Lot of Laughs, High Fives, and Smiles Podcast,” which details the Chicago native’s recent beer-chugging interaction with the former NFL quarterback on Bridge Street in Vail last weekend.
“If you know a lot of Bears fans, there seems to be a debate where half the people hate him and half the people love him,” Bossong told the Vail Daily this week. “I’m 100% on the side of just loving him. And now that he likes to ski — he’s just top of the line of all-time quarterbacks for me.”
Bossong was in Vail for a ski trip with some friends over the weekend when they found themselves sitting at a table on Bridge Street next to Cutler. The ensuing video went viral on ESPN, Barstool, NBC and other major networks — many of which missed the mark on exactly what happened.
“Cutler challenges fan to chug beer for picture” the NBC Sports headline says. “Jay Cutler made a fan chug a pitcher of beer before taking picture,” BroBible reported. While the story of Cutler demanding Bossong chug the beer to take a picture spread across country — and even crossed the language barrier into some Spanish coverage — it was actually quite the opposite.
“Are you done with those beers?” Bossong said he asked Cutler and his friends as they left, collectively, about a pitcher of beer.
He had been waiting respectfully as others bought Cutler and his friends drinks throughout the afternoon — they had all just got off the mountain after a day on the slopes and were enjoying après in the village.
“Don’t say anything stupid,” Bossong remembers the game plan being, fully knowing he had to say something at some point to one of his sports idols.
“It almost felt like fate, the fact that we would end up at the table next to them, they wouldn’t finish their beers, I was so down to chug — it was like an adrenaline rush,” Bossong said, adding he’s not a big beer chugger himself and had to put a few down before talking to Cutler to get that liquid courage.
Bossong was in Vail with his friends Briley Kellison and Joey Falato.
“Don’t freak out right now, but Jay Cutler is sitting directly behind you right now,” Kellison told Bossong.
“I, all of a sudden, turned into like a teenage girl getting ready to go see a Jonas Brothers concert,” Bossong said.
Together, they kept each other calm and cool, waiting for the moment.
“In my head, I am going to be best friends with Jay Cutler,” Bossong remembers thinking.
“Are you done with those beers?” turned into the perfect introduction. Bossong said it’s hard to let unfinished beer go down the drain in a place like Vail, prompting the question.
With dead phones after a day on the slopes, Falato’s portable phone charger saved the day and made the viral video possible — without it, it would have just been a crazy story. And Kellison was quick to film the interaction.
“If we want to hang out with this guy, I think if we buy him a drink it might work good,” Bossong said. “We did the opposite — we asked for his leftover beer.”
Cutler — known for his deadpan, emotionless look — seemed to enjoy the interaction, and eventually took the photo with the friends.
“It kind of looks like he’s one of our boys in the picture,” Kellison said, adding that some media outlets completely messed up the story, saying he was the one who was chugging the beer because it was shared to his Instagram. “Like, if you don’t know who Jay Cutler is, he looks like a slightly older friend of ours, just smiling in the side of the picture. I mean, other than the fact that he’s strikingly handsome.”
But in the video, Cutler looks much different.
“I think that disappointment look in his face, I’m still in debate, I’m not sure if it was ‘I can’t believe this kid is doing this, basically drinking all of our old beers and spilling all over himself,’ or was he just disappointed in my chugging,” Bossong said.
“I think it was a little bit of both,” Kellison said. “It was the classic Jay smirk, though, and I’m happy that he kind of just allowed me to take a video of him.”
Friends, family, coworkers and even strangers reached out about the video. It was all positive, they said.
“The only negative was maybe me spilling, but I think that’s hilarious,” Bossong said. “And anyone who chugs a whole pitcher, they’re going to spill a little unless you’re a really good chugger.”
What’s worse, though, leaving a pitcher of beer behind or spilling a little of that leftover beer?
“I will say I’m a little disappointed in him and his friends for not finishing that pitcher,” Bossong said.
For the friends, it’s a memory and story that will for sure be told over and over again — possibly being more and more embellished as the years go on.
“It is kind of funny, how big of a Bears fan Jack is, he has a podcast, he writes blog posts about the Bears — if this could happen to any one of our friends, it would have been Jack,” Kellison said. “It was just so perfect.”
Check out the podcast for more about Chicago sports, including an episode dedicated to telling the story of Cutler in Vail.
“One of the craziest parts to see about it is just how some of the accounts, the bigger accounts like Barstool, ESPN, they’ll ask for your permission … but then all of the other accounts just kind of take them and run with stories,” Kellison said. “It’s just kind of wild to see how fast things can spread like that once one place posts it.”
So while it’s on brand for Cutler to demand a fan chug a beer to take a photo, it was actually the fan who asked “Are you done with those beers?” that led to the viral interaction.
“Because the Bears quarterback situation has been so bad for so long, he probably is the best quarterback in franchise history — and just his general demeanor,” Bossong said of his love for the quarterback. “A lot of people hate him because he looks like he doesn’t care, but he always just seems to be himself.”
Cutler was an NFL first-round draft pick in 2006 and played for the Broncos before being traded to the Bears before the 2009 season, where he played for eight seasons. He came out of retirement to play for the Dolphins in 2017.