What, James Van Der Beek smug?!

"He comes off a little smug, doesn't he?" Chelsea Lately staffer Chris Fanjola asks his entirely unsympathetic boss, Chelsea Handler, when she's asked to settle which one of them gets to wear the plaid button-down shirt that both Van Der Beek and Fanjola showed up wearing on the same day.

"Don't you have one of your comedy vests you can slap on?" an exasperated Handler asks her longtime guy behind the scenes, who has a deliciously squirmy moment in this exclusive clip from After Lately.

"I would have if he was cooler—but did you know he's not cool?" Fanjola shot back.

When Handler asks Van Der Beek why he should get to wear the hipster shirt, the actor replies, "I'm a guest on this show and this is the shirt I want to wear. Oh, and I'm James Van Der Beek."

Game over, one might say, but then the former Dawson's Creek star gets personal.

"I kind of feel sorry for Chris a little bit," Van Der Beek says. "He's trying to enter this pissing contest and he's just not going to win it. When you replay this scene in your mind when you wake up at 4 in the morning, you're going to realize that there are many instances when you could have taken a different road."

And, burn. (But don't miss the final nail in the pissing-contest coffin, hammered in by—who else—James Van Der Beek.)

GALLERY: Just Another Day in After Lately Hell

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