That Time Jessica Simpson Split Her Pants Open (With No Underwear) While Performing In ‘99

Jessica Simpson performs on the American Idol finale in 2025.
(Image credit: Christopher Willard/Disney)

Jessica Simpson was the Y2K queen. Starting at 17 years old in 1997, she blew away the music industry with her performances and iconic reality TV show moments that still stay in our memories. However, Simpson’s got an unforgettable memory of her own that she's sharing now, and it involves her splitting her pants open with no underwear on in ‘99, and oh my!

The “Irresistible” singer mentioned in September the happy family relationship she has with her sister and her mom. It looks like her family totally came through for her, too, even at the start of her career. Back in 1999, Simpson told ET about accidentally going commando during one of her concerts, and I feel for her:

At Madison Square Garden, my pants ripped totally in half. I mean, like, popped open. I’m bawling. I did not wanna go back out, because I was so embarrassed, and my mom put her jeans on me. So she’s standing back there in just her underwear and a t-shirt.

Way to go, mom! The fact that she was willing to be in just her underwear and a t-shirt so her daughter could wear pants without a rip in them on stage is heroic, honestly.

While you may think splitting your pants is something you’d only see on screen in a SpongeBob SquarePants episode, many other celebs go through it too. Katy Perry’s pants once split while being a judge on American Idol, but she handled the moment with hilarity and fun.

Meanwhile, other on-stage mishaps are bound to happen, too. Jessica's sister, Ashlee Simpson, also had a memorable big TV mistake when the wrong music played during her SNL performance. It’s human to make mistakes. But, they’re moments that can make us laugh much later.

I can understand the sheer (pardon the pun) horror that Jessica Simpson must have felt that day. Diving deep into the music biz as a teen, she previously spoke about the pressure of being compared to pop stars like Britney Spears and Christina Aguilera. So, I can only imagine how mortifying it must have been to have a fashion don’t moment in front of an audience. As Simpson watched her ‘99 self speaking about that concert mishap, the now 45-year-old reflected on that unforgettable experience to ET, saying:

My pants were split from the back to the front, and I had no underwear on. I hit a big note, split my pants, and my mom came running backstage, just took her pants off for me. Luckily, she had underwear on.

Thank goodness her mom was there!

The Dukes of Hazzard actress continued to say during her interview that she hasn’t felt the need to give her younger self advice other than to stay true to herself. Simpson has certainly done that, especially later in her career. She and her family recently built a happy life for themselves in Nashville, and she returned to music by channeling her Southern roots with her EPs Nashville Canyon Part 1 & 2. In many ways, Simpson’s journey proves that trusting your own path can lead you to where you’re meant to be.

It may have been awkward for Jessica Simpson when she split her pants with no underwear back in ‘99. But if anything, you can argue that her pants-splitting moment made her all the more relatable to her adoring fans. Now, I wouldn't be surprised if Simpson would advise all other singers today to bring extra pants backstage just in case.

Carly Levy
Entertainment Writer

Just your average South Floridian cinephile who believes the pen is mightier than the sword.

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