The 'Dawson's Creek' actor planned to go partying in Las Vegas with boy band 'N Sync in the 90s, but the underage heartthrobs' attempt to share the TV star's driver's license to sneak into the venue failed dismally.
Speaking in a web chat with HuffPost Live, James recalled: "I was in Vegas one New Year's and somebody came by and said, 'N Sync wants to meet you!' And at the time, 'N Sync was the second to Backstreet Boys - it was before they had blown up.
"So, I said, 'OK.' And I met them and they were so sweet. They were so nice. They were such cool kids and I immediately liked them. I remember that night, we were all going to some club and they were all too young.
"And so I went in and somehow passed my I.D. back so that Justin could get in with my I.D. Justin used it to get in and then tried to pass it off to [Lance Bass] to get in. By the third time [the bouncers]saw a James Van Der Beek I.D., they were like, 'Ah, I don't think so, James.' "
The 37-year-old actor also discussed landing his iconic role as boy next door Dawson Leery in teen sitcom 'Dawson's Creek', admitting that 'Entourage' star Adrian Grenier originally also auditioned for the part and the rising stars shared an extremely awkward flight to Los Angeles on their way to meet with producers.
He said: "We were both testing for the same role and they sat us next to each other on the plane."
However, James insists things between actors are normally very friendly.
He added: "I haven't really seen much cattiness. There's enough work for everybody."