Olivia Rodrigo Performs ‘If It Makes You Happy’ Duet with Sheryl Crow in Nashville: ‘Pinch Me’

The performance with Sheryl Crow makes Olivia Rodrigo happy!

The singer-songwriter duo took the stage together at The Bluebird Café, an iconic Nashville venue, on Friday night to perform an intimate, stripped-down cover of one of Crow’s biggest hits, “If It Makes You Happy.”

Rodrigo, 20, documented the special evening in an Instagram post, sharing a silly photo of her and Crow, 61, posing together in lounge chairs while holding magazines.

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On the next slide, sour the singer shared a video of the stunning duet, accompanied only by Crow on acoustic guitar.

The duo won over the audience as they sat side by side on chairs on the small stage in the hall.

“Pinch me!” the pop-punk musician captioned the post. “I sang one of my favorite songs of all time with the greatest of all time @sherylcrow !!!! what an honor!!!!”

The “Real Gone” singer then shared a post on her Instagram Story, where she praised Rodrigo, writing: “She’s just so good, y’all!”

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The “All I Wanna Do” singer also shared Rodrigo’s post on her main feed, writing: “The funniest day ever with the unbelievably brilliant @oliviarodrig!”

“What a talent!!” she added. “And the most beautiful young woman!”

Other performance videos shared on X (formerly known as Twitter) show Rodrigo taking the Bluebird Café stage solo to sing several songs from his second album, including “Lacy,” “Vampire” and “Making the Bed.”

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The last time Crow and Rodrigo appeared on stage together, it was in front of a much larger crowd.

In March 2022, the legendary singer-songwriter presented the Disney Channel student with the Woman of the Year award at Billboard’s Women in Music event.

On the red carpet, Crow — who will be inducted into the Rock & Roll Hall of Fame in November — expressed her excitement about the moment to PEOPLE.

“I’m happy to celebrate her,” the singer said about Rodrigo. “I think he’s going to be around for a long time. He deserves to be where he’s celebrating this moment.”

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Crow also shared advice for the star, who was just 19 at the time.

“I just want to tell her, enjoy it. Just enjoy it. Because sometimes you’re so burdened [on] ‘What am I going to do next? What [do] Me next?’ And you forget to enjoy those little moments,” she told PEOPLE.

Sheryl Crow and Olivia Rodrigo at Billboard’s 2022 Women in Music Awards, where Crow presented Rodrigo with the Woman of the Year award. Kevin Mazur/WireImage (2)

Before the show, the star said she had yet to meet Rodrigo in person – but confirmed she was a fan.

“We sing her songs on the way to and from school,” Crow said of her sons Levi, 13, and Wyatt, 16.

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“Actually, we were playing pool the other night, [Levi] sang ‘Good 4 U,'” she said. “He’s pretty good. But you know what? He prefers NFL and NBA. Sorry, Olivia.”

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On the carpet before the show, Rodrigo told PEOPLE that—just like her duet with Crow in Nashville—accepting the award was a big “pinching moment.”

“I think it’s always really cool whenever I meet someone who’s been influenced by my songs,” she said at the time. “Sometimes girls will come up to me and say, ‘Oh my God, your song really helped me through a tough time.’ And there is nothing more special than that.”

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