[Watch] Willie Nelson Treats Crowd To Surprise Jessica Simpson Duet On “I Will Be Your Fool”

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Willie Nelson had an unlikely duet partner share the stage with him during a recent performance at the Orange Country Fair on Aug. 9. Mid-set, the country legend called out a friend to join him and that pal was former pop singer Jessica Simpson.

“My good buddy Jessica Simpson and I are gonna sing a song together,” Willie told the California crowd. Jessica then walked out on stage donning a sequined black dress and knee-high stiletto cowboy boots. The two singers embraced in a hug before launching into “I Will Be Your Fool.” While Jessica kicked off the song on vocals, Willie stood beside her and accompanied on guitar. They’d later trade verses and harmonize on the chorus together as the crowd screamed in approval.

As the song came to a close, Jessica belted the last line before giving the country singer a hug, exclaiming, “I love you, Willie!” Jessica shared her excitement for the appearance on Instagram, noting that it was the first time her family witnessed her perform.

“It’s not every night that a legend invites you to join him on his stage. And my husband and kids got to see me perform for the first time! I love you @willienelsonofficial,” she captions an image of their performance.

In another photo, she shared what happens with her kids before the show. “Backstage shenanigans,” she captions a shot of her husband trying to take a family selfie.

Backstage shenanigans

A post shared by Jessica Simpson (@jessicasimpson) on

Although an unlikely pairing, this isn’t the first time Jessica and Willie have shared the spotlight. In 2005, they co-starred in the film adaption of Dukes of Hazzard. In the film, Jessica famously played Daisy Duke while Willie portrayed Uncle Jesse Duke.

Jessica also released a country album in 2008 titled Do You Know. The project followed the Texas native’s 1999 pop project Sweet Dreams. She’d go on to release a holiday album, Happy Christmas, in 2010.

Annie Reuter
Annie Reuter is a freelance journalist based in Nashville. When she's not covering the latest music news or interviewing countless country artists, she can be found at a writers round listening to the best up-and-coming songwriting talent Music City has to offer.

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