It's hard to portray a character after playing such an iconic heartthrob like Dawson Leery, but James Van Der Beek was lucky enough to stumble upon the perfect role to escape that Dawson's Creek's shadow: himself. While Don't Trust the B**** In Apartment 23 only lasted a season and a half on ABC, those who were fortunate enough to catch the underrated sitcom during it's run got to witness an artist at work.

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James Van Der Beek as James Van Der Beek was equal parts desperation and glam. Following in the footsteps of other actors who have played fictionalized versions of themselves, like Bill Murray (Zombieland) and Neil Patrick Harris (Harold and Kumar Go To White Castle), "Beek" was able to morph his persona from lovable 90's icon into something much zanier and hilariously more shallow.

Worst: June & James' Sex Tape

When a sex tape of James & June gets accidentally leaked, James becomes desperate to manage the situation the best he can. In his search for a resolution, he hits some of his most hollow notes with regards to his own vanity and reputation. He questions his looks, his future with Dancing With The Starsand even his own sexual performance. The cherry on top of this cringe scenario is when Beek exclaims half-heartedly "I think I'm a Sexy Beast." Certainly a low moment for James' confidence and possibly an even lower moment for his character.

Best: James' Energy Drink Commercial

In the final minute of the extremely quotable Don't Trust The B**** In Apartment 23 pilot, a poorly made commercial for a Vietnamese energy drink featuring JVDB comes on. Rocking a flannel and an American flag bandana, James prances around in front of a green screen, showing places like Mt. Rushmore, the Hollywood Hills, and even the moon. The commercial itself is trying so hard to seem American, but in the end, the attempts to capture that Americana energy don't pan out. What they get instead is a bizarre, outlandishly cheap, and endlessly nonsensical piece of advertising. The shoot is so bonkers that by the end of the commercial, James starts questioning the commercial and his own appearance in it. Luckily those moments of confusion are left in and it only makes the moment that much funnier.

Worst: James Is A Giant Peach

In an alternate universe episode, James becomes weak and overall content with his place in the world. After continuing to secretly date a girl he loves, James begins to gain weight at a rapid pace. He quickly tries to shift the attention off of him and his sudden and drastic body change but to no avail. Eventually, he realizes his own destruction but not before lighthearted but bland jokes are thrown around about his size. "Oh my, James is a Giant Peach" is probably one of the worst jokes the show has ever given to its audience. Plus the optics of watching James hit his lowest of lows and it's basically all about his weight, is a little problematic.

Best: Le Beek Chic C'est Beek

Attempting to say "Le Beek Chic C'est Beek" alone was enough to get June and Chloe laughing. When James makes his own fashion line named clumsily after himself, his "Beek Jeans" are quickly moved to the "Chill Out Corner" after they are realized to be overstocked and generally unpopular. Watching James rationalize his own passion project while the world continues to ignore his reasonings is a combination of greatness. The "Beek Jeans" come back in a few other episodes and moments, each time reminding us of the sheer ridiculousness of the jeans that "were not designed for motion."

Worst: Dawson's Creek Reunion

In an attempt to prescribe James with some sort of confidence, Chloe takes it upon herself to write fake letters from the cast of Dawson's Creek begging James to partake in a reunion, knowing full well that he'll experience great joy in replying "No." While cameos are made by other past sitcom stars like Frankie Muniz (Malcolm In The Middle) and Mark Paul Gosselaar (Saved By The Bell), it's not enough to save this lazy development of James' character.

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Overall, we don't learn much about James in a situation which could have led to a lot of interesting developments. It's a perfect setup with a pretty underwhelming payoff, most of the best moments in the episode belong to everyone else, not Beek.

Best: Professor Van Der Beek

When James gets a teaching job for an acting class at NYU, like other celebrities, he's incredibly excited to bestow the knowledge he has been graced with. The reaction from the students, however, mostly consists of requests to hear about Dawson's Creek. James pleads and pleads, but the students are relentless. This moment is what helped the idea for JVDB to play himself, pay off. It came in the second episode and it ensured the early viewers that this weird and meta idea for casting, was not just a good one, but one with massive comedic potential.

Worst: Pop-Up Theater

In probably the most pretentious Beek moment in the show ever, James tweets out that he'll be performing at Mark's coffee shop and arrives in front of Mark who is sweating bullets trying to take care of these new, random customers. His attempt to reassure Mark ends with him telling Mark to get him a water and then continues to perform Shakespeare. He gets really into it too, but in the end, storms out after realizing the customers still only see him as Dawson. The kicker in the scene is the moment where Beek is tastelessly looking off into the distance and says "I walk a lonely road."

Best: "Get My Tween On"

James gets the part opposite Mad Men child star Kiernan Shipka in a Freaky Friday, body-switching type movie. When the actress arrives, James immediately begins trying to mirror her movements and "Get his tween on." He tries to relate to her by mentioning he got slimed at the Kid's Choice Awards in 04', to which Shipka replies "That's so long ago."

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By the end, James and Kiernan are both seated in the same feminine, cross-legged pose. Something about seeing Sally Draper deny JVDB the chance to say things like "totes cray-cray" makes us appreciate this early season 1 episode just a little bit more.

Worst: Dressing Room

James is understandably annoyed by Dean Cain, especially after bringing back the Beeker nickname, though that doesn't make up for the fact that James and his wildly self-absorbed nature are just as annoying here. The lengths to which James goes to maximize the aura of his slightly smaller dressing room are really hard to see. The whole thing is funny, but gosh it's pathetic.

Best: Sexiest Man Alive

When Chloe accuses June of just agreeing with whoever People magazine calls "The Sexiest Man Alive" because of herd mentality, she takes over the magazine publisher and forces James onto the cover. This successfully tricks June and she begins to become increasingly more and more attracted to James. Once James finds out, he gets in on the fun and wakes up June in an amazingly shallow and seductive manner. He pretends to spill a smoothie on his shirt, so that he can take it off, then spills more smoothie on his bare chest and proclaims "I'm a messy boy." James teased June a lot, but this was probably the funniest.

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