Asking James Van Der Beek to “take it off” is a phrase you would expect to come out of the mouth of someone who is eager to see his muscular core. Bet you didn’t know that Emmy winner Tony Hale once gave that helpful suggestion to the famous Dawson’s Creek hottie. According to Tony, James had a ton of coats on, and he might not have completely understood the message. Find this funny? So did Conan O’Brien! Tony sat down with the talk show host and comedian and filled him on in his past acting resume—one that includes appearances on The Sopranos playing a nurse.

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Before he was Gary Walsh, Tony was Lauren Graham‘s famous patient in Because I Said So, and IMDB even lists this guy as appearing on Sex and the City.

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Sarah Jessica Parker and Diane Keaton? Yep, this guy is around with the best of the best.

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