It was Ashton Kutcher’s first prank and it might just have been his best. During the series premiere of MTV’s Punk’d in 2002, right around the time Justin Timberlake was striking out on his own with a solo album, the pop star was confronted by “IRS agents” who were repossessing his home, cars, priceless possessions and even his dogs because he supposedly owed $900,000 in back taxes. The singer panicked, called his mom and cried it out on the stairs until Kutcher revealed it was all one big joke. But Timberlake must have gotten over his embarrassment because he returned to the show three episodes later to help punk Kelly Osbourne. He also spoofed Kutcher in a 2003 episode of Saturday Night Live.