Class of 1995, Cheshire Town Scholar, 1977-2026
It is with profound sadness that Cheshire Academy mourns the passing of James Van Der Beek ’95, who died on February 11, 2026, following a courageous battle with colorectal cancer. He was 48 years old.
James embodied everything the Cheshire Town Scholar award represents: scholarship, citizenship, ambition, and leadership. Selected in 1991 as the recipient of this prestigious honor—which has provided one incoming ninth grader from Cheshire with a full four-year scholarship annually since 1937—James proved worthy of that distinction many times over during his years at the Academy and throughout his remarkable career.
As a student, James demonstrated the extraordinary determination that would define his life. His days at Cheshire Academy began like any other student’s—breakfast, then classes. But by early afternoon, James was boarding a train to Manhattan for rehearsals, returning home around 10 p.m. to complete his homework, only to wake and do it all again.
“I had a passion,” James reflected in a 2018 interview with 1794 Magazine. “It’s something that I knew I wanted to do, that I needed to do. I still marvel that, for a year and a half, I would make trips to New York and have nothing to show for it. I told myself, the industry just didn’t get me yet.”
The industry soon would. During his junior year, James landed a role in the New York City premiere of Edward Albee’s Finding the Sun, earning a rave review from The New York Times that praised him as “refreshingly unselfconscious.” Meanwhile, he maintained his academic excellence, graduating second in his class while simultaneously performing in professional theater and filming his feature debut.
James never forgot the role Cheshire Academy played in his success. The Academy’s flexibility—allowing him to fax in homework and term papers, working with him when rehearsals demanded his time—made his dual path possible.
“Cheshire Academy really came through in supporting me,” James said in 2018. “It meant missing class time and they worked with me. Had I gone to Cheshire High School, and it’s a very good school, I don’t think it would have been possible. They respected what I was trying to do and gave me support and encouragement. I’m very thankful.”
That gratitude led James back to campus repeatedly throughout his career. In 2017, he visited with students in the classroom, workshopped with the theater program, and spoke to the entire student body at Gideon Welles Dining Commons.
In 2020, during the unprecedented circumstances of the COVID-19 pandemic, he graciously delivered a virtual address to the Class of 2020, offering wisdom, warmth, and encouragement to graduates navigating an uncertain world.
Watch James Van Der Beek’s address to the Class of 2020:
Career
James’s breakthrough came with the role of Dawson Leery in Dawson’s Creek (1998–2003), which made him a household name and helped define a generation of television storytelling. He followed this with his memorable turn as quarterback Jonathan “Mox” Moxon in Varsity Blues (1999). Rather than rest on the laurels of his early success, James continually challenged himself with diverse roles, earning particular acclaim playing a satirical version of himself in Don’t Trust the B— in Apartment 23.
A Posthumous Honor
Prior to his passing, James had been nominated and selected to be inducted into Cheshire Academy’s D. Robert Gardiner Arts & Letters Alumni Hall of Fame—a recognition of his extraordinary contributions to the arts and his enduring connection to our community, an honor which he had accepted.
We will honor and remember James during our Reunion 2026 Weekend on June 12-14, where he will be posthumously inducted into the Hall of Fame. This celebration will serve not only as a tribute to his remarkable career but as a testament to the values he embodied as a student, artist, and human being.
A Legacy of Light
The Cheshire Academy community extends its deepest condolences to the Van Der Beek family. We are forever grateful for the ways James represented our school, returned to support our students, and reminded us all that passion, perseverance, and gratitude can carry us further than we ever imagined.
From the stage at Cheshire Academy where he starred in Grease, to the sets of Hollywood’s most beloved productions, James Van Der Beek carried with him the spirit of Cheshire Academy: the belief that with support, dedication, and courage, young people can achieve extraordinary things.
Rest in peace, James. You will be deeply missed.
Read Van Der Beek’s story in the 2018 issue of 1794 Magazine:
