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The Mickey Mouse Club was a variety show that featured some of Hollywood’s most famous names. Stars on the series in the 1990s included Britney Spears, Justin Timberlake, Ryan Gosling, and Christina Aguilera.

Yet one of the people who auditioned and didn’t make the cut was Jessica Simpson. The singer-songwriter was devastated after trying out for the TV show, knowing the moment she auditioned that she wouldn’t get the part. And to make matters worse, Timberlake caused her to start sobbing moments after her performance. Keep reading to find out why.

Jessica Simpson On Stage
Musician Jessica Simpson performs during the Dreamchaser Tour at the Golf Mill Mall, Niles, Illinois, September 7, 2001 | Paul Natkin/Getty Images

Jessica Simpson was so close to getting on ‘The Mickey Mouse Club’

Simpson was hopeful that she’d get the part on the Disney variety series, assuming it would be her claim to fame. Before her final audition, the potential cast members hung out at camp for two weeks to determine their chemistry as a group. As a result, she became extremely good friends with the cast.

Portrait of Jessica Simpson
Portrait of Jessica Simpson | Steve Azzara/Corbis via Getty Images

Simpson reveals in her book that her hopes were extremely high that she would make it.

“There were eleven of us, and the term ‘Top Eight’ became the Holy Grail,” she writes. “Throughout my time at camp, my parents kept hearing, ‘She’s going to make it. She’s our Top Eight.’ At one point, Matt Casella (the casting director) came up to me and my parents. ‘Jessica, it looks really positive,’ he said. It was one thing for my parents to think I had talent, but these professionals were now telling them their daughter had the potential to be a star.”

Justin Timberlake made Jessica Simpson cry after her failed audition

According to Simpson, she was incredibly nervous about her Mickey Mouse Club audition. She was set to sing for the casting crew after Christina Aguilera, and she felt like it would be an impossible act to follow.

“My nerves started settling in,” she writes. “I had to follow that. Just typing this now, I am like, ‘Here we go. Cue the crash.”

As Simpson tells it, she “just froze” on stage. “My choreography was completely off, and then I couldn’t remember any of the lines from my monologue. I stared at the camera and knew I’d blown it completely. The theater was silent.”

She then ran off stage, trying not to cry. Timberlake, who was about to go on, fed into her insecurities.

“‘Oooooooooh,’ Justin said, his eyes so wide, his mouth open like a slack-jawed cartoon. ‘What did you just do?'”

“That started the tears,” Simpson writes. “Oh, I cried. I cried big heaving sobs. My parents came to me, asking again and again, ‘What happened? What Happened?’ I choked. I crashed down to earth, landing right on top of them.”

Jessica Simpson remained friends with the ‘Mouseketeers’ later on in life

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Because she became so close with the other cast members, she was all the more crushed when she didn’t get the part. “I had grown so close to these people,” she writes, “and I thought we were all going to be on an adventure together.”

Fortunately, though, Simpson was able to find success as an artist on her own without the help of the variety series.