James Van Der Beek

School days started for James Van Der Beek ’95 as they would for any average Cheshire Academy student. He’d wake up, eat breakfast and head to class. But right before lunch, the crunch began for Van Der Beek and continued long into the evening.

In the early afternoon, he drove to New Haven to catch a train to Manhattan. Van Der Beek got some of his school work done during the nearly two-hour ride before he boarded a subway to a rehearsal studio. Several hours later, he was back on Metro North heading home. While others were snoozing, the teen-aged Van Der Beek studied his lines on a train full of commuters in business suits.

He got home around 10 p.m. and did his writing assignments, which he couldn’t do on the train because the ride was too bumpy. Van Der Beek then slept for a few hours, woke up, and did it all over again the next day.

“I had a passion,” Van Der Beek said. “It’s something that I knew I wanted to do, that I needed to do. I still marvel that, for 1 ½ years, 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.”

He finally received his break during his junior year at the Academy. Van Der Beek landed a role as Fergus in the New York City premiere of Edward Albee’s play, “Finding the Sun” performed by the Signature Theater Company. His performance drew a rave review from the New York Times.

“Not all the cast members can handle the dialogue, which is as much composed as written,” the review read. “But Mary Beth Peil, Monique Fowler and Brendan Corbalis can, and James Van Der Beek is refreshingly unselfconscious as a teenager yet to suffer the inevitable tarnish.”

He remembers seeing his theater teacher, Shelley Taylor-Boyd, reading the review after lunch one day.

“That was a great reward for anyone who supported me,” Van Der Beek said. “It was great justification for all their support and patience.”

That performance in the 160seat Peter Norton Space theater served as the launching pad for what has been a successful acting career for Van Der Beek.

He’s best known for his lead role in the iconic teen television drama “Dawson’s Creek,” which aired for six seasons, and his award-winning performance in the movie “Varsity Blues.” He’s also enjoyed a long list of other versatile roles during his career.

Van Der Beek is now starring as a superstar DJ in the VICELAND television comedy “What Would Diplo Do?” He’s also the voice of Boris Hauntley, in this season’s Disney Junior’s cartoon, “Vampirina.” (Van Der Beek’s daughter brags about it, he said, and makes him do the voice in front of her friends). He also plays an anesthesiologist in the film “Downsizing,” which hit theaters last December. Van Der Beek also appeared in an episode of “Modern Family” and will play a financial kingpin in a new FX show, “Pose.”

Van Der Beek, who lives in Los Angeles with his wife and four children, says he’s at a point in his career now where he can afford to take only the projects he really loves. He says he wants to get back to doing some theater. He’s also enjoying show running and producing.

He’s come a long way since starring as Danny Zuko in the Academy production of “Grease” in the Gideon Welles Dining Commons. Boyd remembers seeing Van Der Beek for the first time in the Cheshire Youth Theater productions of “Wizard of Oz” and “Grease.”

“He was spot on for everything,” she recalled, noting that he wasn’t even in high school yet.

“The way he moved his body, the way he interpreted his role,” Boyd said, “I went right up to his mother after the show and told her that he was going to be a big star."

Brian Canell ’95, a classmate of Van Der Beek’s, was a cast member in the Academy production of “Grease.” He was impressed with how Van Der Beek balanced school work and his budding acting career. While a student, he was filming “Angus,” his feature film debut, and performed eight shows a week at the Goodspeed Opera House in East Haddam, Connecticut during his senior year. “Somehow he managed to handle all that,” Canell said. “He never seemed to let that bother him. His attitude was, 'this is what I’m doing, this is what I have to do, to make this work.’ I was amazed by how effortless it seemed for him. He just had that sort of enthusiasm and ambition that you knew he was going to take off.”

Cheshire Academy was very supportive through the process, Van Der Beek said. His teachers were flexible and worked with him. Van Der Beek, a Town Scholar, did his part and kept his grades up. He graduated No. 2 in his class. When he was in New York, teachers allowed him to fax in his homework and term papers. “Please send to Mr. Gardiner” one assignment read, as a bunch of curled up paper passed through Bowden Hall’s fax machine.

“Cheshire Academy really came through in supporting me,” Van Der Beek said. “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.”