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Justin Timberlake made pop culture history for a few reasons, and fans can’t forget about his time on Punk’d. When Ashton Kutcher turned into a master prankster on the MTV series, he also helped the show become a guilty pleasure for those who loved to watch celebrities squirm.

Some flipped out, some worried, some were frightened, and some, like Timberlake, nearly shed tears. The singer recently opened up about the reason he was so emotional in the season 1 episode, which is both funny and touching.

Justin Timberlake
Justin Timberlake attends the 2018 iHeartRadio Music Festival | JB Lacroix/WireImage/Getty Images

What happened to Justin Timberlake on ‘Punk’d’

It was 2003 when Punk’d debuted its first season with Justin Timberlake as a naïve participant in a run-in with the IRS. Kutcher — whose team included Dax Shepard and Al Shearer — sat in his hideout as phony agents began seizing Timberlake’s property.

Boxes and a flatbed truck were awaiting the singer when he arrived home from a golf outing with a friend. Shepard, who was dressed in navy blue “agent” jacket, explained to Timberlake that he owed the IRS $904,000 and his house was under seizure.

Shepard advised the singer that everything would need to be settled in court. A distraught looking Timberlake grew more upset when his friend approached and said they were taking his dogs too.

He learned assets in Florida and Tennessee were also taken, and at one point, Shepard tried to take Timberlake’s phone. He kept frowning and rubbing his head as he waited for his mother to arrive. When Shepard and crew broke a guitar, Kutcher swooped in to keep Timberlake from going off.

Justin Timberlake Ashton Kutcher
Justin Timberlake poses with actor Ashton Kutcher during ‘ten’ fashion show presented by General Motors, 2003 | Vince Bucci/Getty Images

Timberlake said he was stoned during ordeal

Timberlake appeared on Shepard’s Armchair Expert podcast and the pair touched on that famous Punk’d episode. As they reminisced, Shepard said his first impression of Timberlake was based on that prank.

His takeaway? Timberlake was a good dude because he really cared about his dogs more than his house and material things.

However, Timberlake chimed in with an explanation and credits that day for his marijuana hiatus. After his Punk’d experience, he swore off cannabis for a while. He said he was stoned when he arrived home from playing golf with his buddies and found the “IRS” there.

“I remember I sat down on the porch on the front steps, and I looked at Trace and I was like, ‘I’m so high man. Is this real?’” said Timberlake. He then explained the dogs were his mother’s and meant the world to her. He thought they were being confiscated and it would devastate his mom.

Timberlake said his mother’s role in the prank convinced him losing the dogs would be terrible. “When the dogs got involved, that’s when all bets were off,” he said, adding that he had an unsettling thought. “What if my mom never sees her dogs again? Will she ever forgive me?” Timberlake shared. The effect of the weed escalated his feelings.

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Shepard received strict instructions from MTV for Timberlake

For his part, Shepard remembered the prank fondly and thanked Timberlake. He said it helped take his career to another level. On the flip side, Shepard was under pressure not to jeopardize MTV’s relationship with Timberlake by allowing the Punk’d scheme to go left.

“I was in your garage for an hour and a half being told everything I could and couldn’t say,” Shepard told Timberlake. He shared that he wanted to keep the prank on course but had to be careful not to lose his gig. Both he and Timberlake laughed about it and acknowledged it’s still the most popular episode in the series.