On the first Monday in May, New York City typically finds itself divided between two cathedrals of culture: the Metropolitan Museum of Art, where the fashion elite gather for the Met Gala, and Madison Square Garden, the hollowed ground for New York sports. On May 4, 2026, this divide became a literal battleground for celebrity loyalty as the Met Gala coincided with Game 1 of the NBA Eastern Conference Semifinals between the New York Knicks and the Philadelphia 76ers.
For two of the Knicks’ most visible celebrity superfans, Timothée Chalamet and Ben Stiller, the night required a difficult choice. While both are regulars in the “Celebrity Row” at the Garden, they navigated the scheduling conflict in starkly different ways, sparking a viral debate about the true definition of a “die-hard” fan.
Timothée Chalamet: The Courtside Connoisseur
Timothée Chalamet, the Oscar-nominated actor and native New Yorker, made his priorities clear by snubbing the Met Gala in favor of the hardwood. Despite his status as a fashion icon—and the fact that his girlfriend, Kylie Jenner, was attending the Gala in a custom Schiaparelli gown—Chalamet was spotted courtside at Madison Square Garden.
Dressed down in a casual jacket and a Knicks cap, Chalamet looked entirely at home as he watched the Knicks dominate the 76ers. When asked about his decision to skip the “Oscars of Fashion,” Chalamet reportedly described the Knicks’ current playoff run as the “most fun period of my life.” For Chalamet, the allure of a deep playoff run for his hometown team outweighed the prestige of the red carpet. Social media was quick to crown him the ultimate fan, with many users noting that “Respect to Chalamet” was trending as he chose the intensity of a playoff atmosphere over the curated glamour of the Met.
Ben Stiller: The Fashion-Forward Fan
On the other side of town, Ben Stiller found himself in a more complicated position. A fixture at Knicks games for decades, Stiller opted to attend the Met Gala alongside his wife, Christine Taylor. However, Stiller made sure his heart—and his wardrobe—remained at the Garden.
In a clever nod to the team, Stiller wore a tailored navy suit paired with a vibrant orange tie, while Taylor donned a cobalt blue gown featuring floral sequin embroidery. Together, they represented the Knicks’ orange-and-blue color palette on the red carpet. Even while posing for the world’s photographers, Stiller couldn’t keep his mind off the score. At one point, he held up six fingers to photographers, signaling his series prediction: “Knicks in six.”
“My heart is at MSG,” Stiller told reporters on the carpet, admitting he planned to watch the game on his phone once he got inside the museum. Despite his sartorial tribute, Stiller faced some lighthearted “backlash” from the sports world. Barstool Sports founder Dave Portnoy joked that Stiller might have to “turn in his fan card,” while others lamented his absence during a pivotal Game 1.
A Tale of Two Cities
The night ended in a blowout victory for the Knicks, who defeated the 76ers 137-98. The lopsided score allowed Stiller to joke on social media later that night that he might “have to go to the Met ball every game” if it meant the Knicks would continue to win by nearly 40 points.
The contrast between Chalamet and Stiller highlights the unique cultural intersection of New York City in May. On one hand, you have the Met Gala, an event that raised a record $42 million for the Costume Institute in 2026. On the other, you have a Knicks team that has revitalized a city’s spirit, making a ticket to the Garden the hottest commodity in town.
While Chalamet may have won the “fan of the night” award from the sports blogs, Stiller’s long-term dedication to the franchise remains undisputed. As the series moves to Game 2 on Wednesday, both stars are expected to be back in their usual seats, traded the tuxedos and cameras for jerseys and cheers, as the Knicks continue their quest for a championship in what many fans believe is finally “their year.”
