One of the most memorable episodes involved Justin Timberlake being told his house was repossessed by the IRS for unpaid taxes.
Shepard reminisced about that episode on Marc Maron's WTF podcast last week. His retelling of the story is quite hilarious. The ABC star explained that the cast members were not allowed to fight if a celebrity became physical during a prank.
Shepard explained, "As Ashton and I became friends, he said, 'You know, you can't, if someone gets physical with you, you're just going to have to take it.' Which, weirdly enough … definitely the most famous bit on the show in all the years was the Punk'ing of Justin Timberlake. What made it so viral, I guess, was that he had cried at one point in it."
The "Mirrors" singer became visibly upset about the boxes being moved out of his home as the sketch went on and on about the debt owed to the government. Even the reveal of the joke did not quell Timberlake's anxiety.
Shepard continued, "And at the end of that bit, when Ashton comes out [and says], 'You're on Punk'd' blah blah blah,' and everyone is celebrating … the bit is over, the cameras are off, and [Timberlake] keeps saying, 'Yeah, man. I was about to f***ing punch you.' And I was like, 'Mmm hmm, all right.'
"'Dude, I was, for real, man, I was about to f***ing punch you out,'" [Timberlake continued]."
The star analyzed how he really felt about Timberlake threatening him.
"And I'm like, OK, that's number two. I'm thinking how many times can I hear this dude in his golf outfit — he was wearing a golf outfit — tell me he can punch me out before I'm just not going to be able to handle it.
"And god bless Ashton. He goes, 'When were you going to punch him? Before or after you were crying?'"
The infamous episode was part of the series premiere on March 17, 2003.
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