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Home Culture

James Van Der Beek was always in on the joke

by Yonkers Observer Report
February 12, 2026
in Culture
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What made the WB’s “Dawson’s Creek” work so well was that it was a teen drama that took teenagers seriously, while also having fun at the fact that not a single one of its four lead characters talked like teenagers (or even most humans), what with their SAT-caliber vocabularies and deep understanding of arts and culture.

“Dawson’s” ended in 2003, capping off a six-season run that helped usher in a wave of smarter, sleeker teen programs like the CW’s “Gossip Girl” and a mainstreaming of chat rooms and fan fiction (the granddaddy of snarky recap sites, Television Without Pity, was established in 1998 specifically to dissect “Dawson’s” scripts).

But, as time went on, no one seemed to get the dichotomy of “Dawson’s” better than the show’s lead actor, James Van Der Beek.

The other three stars of that show fought hard against that trope and typecasting. Joshua Jackson is known as much for provocative streaming and cable dramas, like Peacock’s “Dr. Death” and Showtime’s “The Affair,” as he is for reveling in the camp of ABC’s comically absurd medical drama “Doctor Odyssey.” Katie Holmes’ acting was overshadowed by the media scrutiny of her personal life and her marriage to Tom Cruise, even as she held her own on stage and as a director and actor in indie projects (she seemed to be having a lot of fun in the last season of Peacock’s “Poker Face”). Five-time Oscar nominee Michelle Williams is such a respected talent that Steven Spielberg asked her to play a version of his mom for his film “The Fabelmans.”

Van Der Beek, who died Wednesday after a colorectal cancer diagnosis, seemed to embrace the ethos of joining in everyone’s fun when there’s no sense of trying to beat it.

The image most people likely conjured as soon as they heard of Van Der Beek’s death was of him, as Dawson, crying on a dock. In context, the image is from a 2000 episode of the series and shows a teenager’s agony over losing the love of his life to his best friend. Out of context, it looks ridiculous. Because, aside from when you’re the teen in question, it almost always looks ridiculous when a kid is just an overemotional, theatrical mess of a broken heart.

Van Der Beek, to his credit, embraced this. In 2011, he released a Funny or Die video explaining the viral GIF’s backstory and how he allegedly planned to monetize it.

“You know, the more I saw [the image] in website comments sections mocking the sadness of others, the more I realized what the internet was really demanding: more intense, emotional close-ups of my face,” he deadpanned.

In fact, much of his post-“Dawson’s” career was really about telling you that he’s in on the joke.

Van Der Beek spent two seasons on the ABC comedy “Don’t Trust the B— in Apartment 23,” playing an exaggerated version of himself and the best friend/accomplice of a roommate from hell portrayed by Krysten Ritter.

“I thought the sense of humor that I’ve had in terms of making fun of fame and myself and all that, which would have seemed ungrateful when I was at the peak of it, now was something that people could kind of also share in,” Van Der Beek told journalists about “Don’t Trust the B—” at the summer 2017 Television Critics Association press tour, where he was promoting an even more meta project: Viceland’s “What Would Diplo Do?” (He played a dim-witted version of the dance music DJ and producer.)

@vanderjames

I was nervous about singing in public. As a kid, I’d let outside voices prevent me from having full confidence in my singing abilities, and some of that insecurity had stuck after all these years… Thank you to my wife and my kids for encouraging me to push through to the other side of fear and do #themaskedsinger Thank you to the producers for inviting me, to the insanely talented costume designers for such a bad-ass character, to Britt for convincing me this song would work, to the musical director for welcoming my arrangement notes and thoughts with zero condescension, to the choreographers for such cool dances I couldn’t see at the time 😂, to Ivan for coaching me to readiness with such care and skill, and to Amy for weaving her magic and helping me tap into what it’s like to sing like ME. And may this be an invitation to everyone to follow their bliss ❤️ #singing #disturbia #themaskedsinger Wednesday nights on Fox

♬ original sound – James Van Der Beek

Life imitated art when, in 2019, Van Der Beek fulfilled the prophecy foretold by a “Don’t Trust the B—” storyline and became a contestant on “Dancing With the Stars.” He also appeared in the celebrity-focused Fox competition series “The Masked Singer” and “The Real Full Monty,” the latter of which he did to raise money for cancer charities. And he gave the millennials who graduated to watching kids’ TV with their children a sense of side-eye when he voiced the dad in Disney Channel’s “Vampirina” (fittingly, “Gilmore Girls’” Lauren Graham voiced the mom).

Van Der Beek did take on serious TV roles; he was a series regular on the CBS procedural “CSI: Cyber” and appeared in the first season of FX’s much-lauded “Pose.” But he never let you forget that he knew what you wanted from him. In one of his last TV roles, Van Der Beek guest starred on Prime Video’s college dramedy “Overcompensating.” In a sort of passing-the-torch moment to that series’ creator and star Benito Skinner, Van Der Beek played Charlie, a middle-aged former frat boy who senses his glory days are behind him.

“Enjoy the day,” Charlie tells Adam DiMarco’s college senior, Peter, before leaving the room to soak up whatever debauchery he can get his hands on before reporting to work on Monday morning.

Childhood goes away. The memories of the people who were integral to it do not.

What made the WB’s “Dawson’s Creek” work so well was that it was a teen drama that took teenagers seriously, while also having fun at the fact that not a single one of its four lead characters talked like teenagers (or even most humans), what with their SAT-caliber vocabularies and deep understanding of arts and culture.

“Dawson’s” ended in 2003, capping off a six-season run that helped usher in a wave of smarter, sleeker teen programs like the CW’s “Gossip Girl” and a mainstreaming of chat rooms and fan fiction (the granddaddy of snarky recap sites, Television Without Pity, was established in 1998 specifically to dissect “Dawson’s” scripts).

But, as time went on, no one seemed to get the dichotomy of “Dawson’s” better than the show’s lead actor, James Van Der Beek.

The other three stars of that show fought hard against that trope and typecasting. Joshua Jackson is known as much for provocative streaming and cable dramas, like Peacock’s “Dr. Death” and Showtime’s “The Affair,” as he is for reveling in the camp of ABC’s comically absurd medical drama “Doctor Odyssey.” Katie Holmes’ acting was overshadowed by the media scrutiny of her personal life and her marriage to Tom Cruise, even as she held her own on stage and as a director and actor in indie projects (she seemed to be having a lot of fun in the last season of Peacock’s “Poker Face”). Five-time Oscar nominee Michelle Williams is such a respected talent that Steven Spielberg asked her to play a version of his mom for his film “The Fabelmans.”

Van Der Beek, who died Wednesday after a colorectal cancer diagnosis, seemed to embrace the ethos of joining in everyone’s fun when there’s no sense of trying to beat it.

The image most people likely conjured as soon as they heard of Van Der Beek’s death was of him, as Dawson, crying on a dock. In context, the image is from a 2000 episode of the series and shows a teenager’s agony over losing the love of his life to his best friend. Out of context, it looks ridiculous. Because, aside from when you’re the teen in question, it almost always looks ridiculous when a kid is just an overemotional, theatrical mess of a broken heart.

Van Der Beek, to his credit, embraced this. In 2011, he released a Funny or Die video explaining the viral GIF’s backstory and how he allegedly planned to monetize it.

“You know, the more I saw [the image] in website comments sections mocking the sadness of others, the more I realized what the internet was really demanding: more intense, emotional close-ups of my face,” he deadpanned.

In fact, much of his post-“Dawson’s” career was really about telling you that he’s in on the joke.

Van Der Beek spent two seasons on the ABC comedy “Don’t Trust the B— in Apartment 23,” playing an exaggerated version of himself and the best friend/accomplice of a roommate from hell portrayed by Krysten Ritter.

“I thought the sense of humor that I’ve had in terms of making fun of fame and myself and all that, which would have seemed ungrateful when I was at the peak of it, now was something that people could kind of also share in,” Van Der Beek told journalists about “Don’t Trust the B—” at the summer 2017 Television Critics Association press tour, where he was promoting an even more meta project: Viceland’s “What Would Diplo Do?” (He played a dim-witted version of the dance music DJ and producer.)

@vanderjames

I was nervous about singing in public. As a kid, I’d let outside voices prevent me from having full confidence in my singing abilities, and some of that insecurity had stuck after all these years… Thank you to my wife and my kids for encouraging me to push through to the other side of fear and do #themaskedsinger Thank you to the producers for inviting me, to the insanely talented costume designers for such a bad-ass character, to Britt for convincing me this song would work, to the musical director for welcoming my arrangement notes and thoughts with zero condescension, to the choreographers for such cool dances I couldn’t see at the time 😂, to Ivan for coaching me to readiness with such care and skill, and to Amy for weaving her magic and helping me tap into what it’s like to sing like ME. And may this be an invitation to everyone to follow their bliss ❤️ #singing #disturbia #themaskedsinger Wednesday nights on Fox

♬ original sound – James Van Der Beek

Life imitated art when, in 2019, Van Der Beek fulfilled the prophecy foretold by a “Don’t Trust the B—” storyline and became a contestant on “Dancing With the Stars.” He also appeared in the celebrity-focused Fox competition series “The Masked Singer” and “The Real Full Monty,” the latter of which he did to raise money for cancer charities. And he gave the millennials who graduated to watching kids’ TV with their children a sense of side-eye when he voiced the dad in Disney Channel’s “Vampirina” (fittingly, “Gilmore Girls’” Lauren Graham voiced the mom).

Van Der Beek did take on serious TV roles; he was a series regular on the CBS procedural “CSI: Cyber” and appeared in the first season of FX’s much-lauded “Pose.” But he never let you forget that he knew what you wanted from him. In one of his last TV roles, Van Der Beek guest starred on Prime Video’s college dramedy “Overcompensating.” In a sort of passing-the-torch moment to that series’ creator and star Benito Skinner, Van Der Beek played Charlie, a middle-aged former frat boy who senses his glory days are behind him.

“Enjoy the day,” Charlie tells Adam DiMarco’s college senior, Peter, before leaving the room to soak up whatever debauchery he can get his hands on before reporting to work on Monday morning.

Childhood goes away. The memories of the people who were integral to it do not.

What made the WB’s “Dawson’s Creek” work so well was that it was a teen drama that took teenagers seriously, while also having fun at the fact that not a single one of its four lead characters talked like teenagers (or even most humans), what with their SAT-caliber vocabularies and deep understanding of arts and culture.

“Dawson’s” ended in 2003, capping off a six-season run that helped usher in a wave of smarter, sleeker teen programs like the CW’s “Gossip Girl” and a mainstreaming of chat rooms and fan fiction (the granddaddy of snarky recap sites, Television Without Pity, was established in 1998 specifically to dissect “Dawson’s” scripts).

But, as time went on, no one seemed to get the dichotomy of “Dawson’s” better than the show’s lead actor, James Van Der Beek.

The other three stars of that show fought hard against that trope and typecasting. Joshua Jackson is known as much for provocative streaming and cable dramas, like Peacock’s “Dr. Death” and Showtime’s “The Affair,” as he is for reveling in the camp of ABC’s comically absurd medical drama “Doctor Odyssey.” Katie Holmes’ acting was overshadowed by the media scrutiny of her personal life and her marriage to Tom Cruise, even as she held her own on stage and as a director and actor in indie projects (she seemed to be having a lot of fun in the last season of Peacock’s “Poker Face”). Five-time Oscar nominee Michelle Williams is such a respected talent that Steven Spielberg asked her to play a version of his mom for his film “The Fabelmans.”

Van Der Beek, who died Wednesday after a colorectal cancer diagnosis, seemed to embrace the ethos of joining in everyone’s fun when there’s no sense of trying to beat it.

The image most people likely conjured as soon as they heard of Van Der Beek’s death was of him, as Dawson, crying on a dock. In context, the image is from a 2000 episode of the series and shows a teenager’s agony over losing the love of his life to his best friend. Out of context, it looks ridiculous. Because, aside from when you’re the teen in question, it almost always looks ridiculous when a kid is just an overemotional, theatrical mess of a broken heart.

Van Der Beek, to his credit, embraced this. In 2011, he released a Funny or Die video explaining the viral GIF’s backstory and how he allegedly planned to monetize it.

“You know, the more I saw [the image] in website comments sections mocking the sadness of others, the more I realized what the internet was really demanding: more intense, emotional close-ups of my face,” he deadpanned.

In fact, much of his post-“Dawson’s” career was really about telling you that he’s in on the joke.

Van Der Beek spent two seasons on the ABC comedy “Don’t Trust the B— in Apartment 23,” playing an exaggerated version of himself and the best friend/accomplice of a roommate from hell portrayed by Krysten Ritter.

“I thought the sense of humor that I’ve had in terms of making fun of fame and myself and all that, which would have seemed ungrateful when I was at the peak of it, now was something that people could kind of also share in,” Van Der Beek told journalists about “Don’t Trust the B—” at the summer 2017 Television Critics Association press tour, where he was promoting an even more meta project: Viceland’s “What Would Diplo Do?” (He played a dim-witted version of the dance music DJ and producer.)

@vanderjames

I was nervous about singing in public. As a kid, I’d let outside voices prevent me from having full confidence in my singing abilities, and some of that insecurity had stuck after all these years… Thank you to my wife and my kids for encouraging me to push through to the other side of fear and do #themaskedsinger Thank you to the producers for inviting me, to the insanely talented costume designers for such a bad-ass character, to Britt for convincing me this song would work, to the musical director for welcoming my arrangement notes and thoughts with zero condescension, to the choreographers for such cool dances I couldn’t see at the time 😂, to Ivan for coaching me to readiness with such care and skill, and to Amy for weaving her magic and helping me tap into what it’s like to sing like ME. And may this be an invitation to everyone to follow their bliss ❤️ #singing #disturbia #themaskedsinger Wednesday nights on Fox

♬ original sound – James Van Der Beek

Life imitated art when, in 2019, Van Der Beek fulfilled the prophecy foretold by a “Don’t Trust the B—” storyline and became a contestant on “Dancing With the Stars.” He also appeared in the celebrity-focused Fox competition series “The Masked Singer” and “The Real Full Monty,” the latter of which he did to raise money for cancer charities. And he gave the millennials who graduated to watching kids’ TV with their children a sense of side-eye when he voiced the dad in Disney Channel’s “Vampirina” (fittingly, “Gilmore Girls’” Lauren Graham voiced the mom).

Van Der Beek did take on serious TV roles; he was a series regular on the CBS procedural “CSI: Cyber” and appeared in the first season of FX’s much-lauded “Pose.” But he never let you forget that he knew what you wanted from him. In one of his last TV roles, Van Der Beek guest starred on Prime Video’s college dramedy “Overcompensating.” In a sort of passing-the-torch moment to that series’ creator and star Benito Skinner, Van Der Beek played Charlie, a middle-aged former frat boy who senses his glory days are behind him.

“Enjoy the day,” Charlie tells Adam DiMarco’s college senior, Peter, before leaving the room to soak up whatever debauchery he can get his hands on before reporting to work on Monday morning.

Childhood goes away. The memories of the people who were integral to it do not.

What made the WB’s “Dawson’s Creek” work so well was that it was a teen drama that took teenagers seriously, while also having fun at the fact that not a single one of its four lead characters talked like teenagers (or even most humans), what with their SAT-caliber vocabularies and deep understanding of arts and culture.

“Dawson’s” ended in 2003, capping off a six-season run that helped usher in a wave of smarter, sleeker teen programs like the CW’s “Gossip Girl” and a mainstreaming of chat rooms and fan fiction (the granddaddy of snarky recap sites, Television Without Pity, was established in 1998 specifically to dissect “Dawson’s” scripts).

But, as time went on, no one seemed to get the dichotomy of “Dawson’s” better than the show’s lead actor, James Van Der Beek.

The other three stars of that show fought hard against that trope and typecasting. Joshua Jackson is known as much for provocative streaming and cable dramas, like Peacock’s “Dr. Death” and Showtime’s “The Affair,” as he is for reveling in the camp of ABC’s comically absurd medical drama “Doctor Odyssey.” Katie Holmes’ acting was overshadowed by the media scrutiny of her personal life and her marriage to Tom Cruise, even as she held her own on stage and as a director and actor in indie projects (she seemed to be having a lot of fun in the last season of Peacock’s “Poker Face”). Five-time Oscar nominee Michelle Williams is such a respected talent that Steven Spielberg asked her to play a version of his mom for his film “The Fabelmans.”

Van Der Beek, who died Wednesday after a colorectal cancer diagnosis, seemed to embrace the ethos of joining in everyone’s fun when there’s no sense of trying to beat it.

The image most people likely conjured as soon as they heard of Van Der Beek’s death was of him, as Dawson, crying on a dock. In context, the image is from a 2000 episode of the series and shows a teenager’s agony over losing the love of his life to his best friend. Out of context, it looks ridiculous. Because, aside from when you’re the teen in question, it almost always looks ridiculous when a kid is just an overemotional, theatrical mess of a broken heart.

Van Der Beek, to his credit, embraced this. In 2011, he released a Funny or Die video explaining the viral GIF’s backstory and how he allegedly planned to monetize it.

“You know, the more I saw [the image] in website comments sections mocking the sadness of others, the more I realized what the internet was really demanding: more intense, emotional close-ups of my face,” he deadpanned.

In fact, much of his post-“Dawson’s” career was really about telling you that he’s in on the joke.

Van Der Beek spent two seasons on the ABC comedy “Don’t Trust the B— in Apartment 23,” playing an exaggerated version of himself and the best friend/accomplice of a roommate from hell portrayed by Krysten Ritter.

“I thought the sense of humor that I’ve had in terms of making fun of fame and myself and all that, which would have seemed ungrateful when I was at the peak of it, now was something that people could kind of also share in,” Van Der Beek told journalists about “Don’t Trust the B—” at the summer 2017 Television Critics Association press tour, where he was promoting an even more meta project: Viceland’s “What Would Diplo Do?” (He played a dim-witted version of the dance music DJ and producer.)

@vanderjames

I was nervous about singing in public. As a kid, I’d let outside voices prevent me from having full confidence in my singing abilities, and some of that insecurity had stuck after all these years… Thank you to my wife and my kids for encouraging me to push through to the other side of fear and do #themaskedsinger Thank you to the producers for inviting me, to the insanely talented costume designers for such a bad-ass character, to Britt for convincing me this song would work, to the musical director for welcoming my arrangement notes and thoughts with zero condescension, to the choreographers for such cool dances I couldn’t see at the time 😂, to Ivan for coaching me to readiness with such care and skill, and to Amy for weaving her magic and helping me tap into what it’s like to sing like ME. And may this be an invitation to everyone to follow their bliss ❤️ #singing #disturbia #themaskedsinger Wednesday nights on Fox

♬ original sound – James Van Der Beek

Life imitated art when, in 2019, Van Der Beek fulfilled the prophecy foretold by a “Don’t Trust the B—” storyline and became a contestant on “Dancing With the Stars.” He also appeared in the celebrity-focused Fox competition series “The Masked Singer” and “The Real Full Monty,” the latter of which he did to raise money for cancer charities. And he gave the millennials who graduated to watching kids’ TV with their children a sense of side-eye when he voiced the dad in Disney Channel’s “Vampirina” (fittingly, “Gilmore Girls’” Lauren Graham voiced the mom).

Van Der Beek did take on serious TV roles; he was a series regular on the CBS procedural “CSI: Cyber” and appeared in the first season of FX’s much-lauded “Pose.” But he never let you forget that he knew what you wanted from him. In one of his last TV roles, Van Der Beek guest starred on Prime Video’s college dramedy “Overcompensating.” In a sort of passing-the-torch moment to that series’ creator and star Benito Skinner, Van Der Beek played Charlie, a middle-aged former frat boy who senses his glory days are behind him.

“Enjoy the day,” Charlie tells Adam DiMarco’s college senior, Peter, before leaving the room to soak up whatever debauchery he can get his hands on before reporting to work on Monday morning.

Childhood goes away. The memories of the people who were integral to it do not.

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