The singer-songwriters shared the stage at Nashville's Bluebird Cafe.
This is a duet sure to make any music lover happy. On Friday, Olivia Rodrigo was joined by Sheryl Crow during her acoustic set at the historic Nashville venue, the Bluebird Café. The pair gave fans a surprise performance of an intimate, stripped-down arrangement of "If It Makes You Happy," one of Crow's biggest hits.
The 20-year-old singer shared a brief snippet of the duet on her Instagram page, alongside a sweet photo of her and Crow posing together in salon chairs while holding up Vogue Magazines. In the video, the duo softly croons the song's iconic chorus as they sit side-by-side on the venue's small stage, and Crow plays the guitar.
"Pinch me!" Rodrigo captioned her post. "Sang one of my favorite songs of all time with the greatest of all time @sherylcrow !!!! what an honor!!!!"
Crow equally enjoyed the surprise performance. Resharing Rodrigo's post on her own Instagram account, she wrote, "Funnest day ever with the amazingly brilliant @oliviarodrigo! What a talent!! And the loveliest young woman!"
The 61-year-old also shared the post to her Instagram Story, where she praised Rodrigo's vocal skills, writing, "She is just really good, y'all!"
Fans posted other videos of Rodrigo's visit to the Bluebird Café to X (formerly known as Twitter), showing the High School Musical: The Musical: The Series alum performing several tracks from her sophomore album, Guts. She performed "Lacy," "Vampire," and "Making the Bed."
Crow and Rodrigo first crossed paths at Billboard's 2022 Women in Music event, where the "Soak Up the Sun" singer presented Rodrigo with the "Woman of the Year" honor.
"Oh my gosh, it's incredible," Rodrigo gushed to ET on the night of the special event. "I mean, writing songs is just my favorite thing in the whole world, and so to be recognized in this way, is absolutely surreal, and I'm just so grateful to everyone who has supported me this year."
"[I'm] excited for what's to come," she added.
When asked what she would tell a younger version of herself, Rodrigo told ET, she'd tell her to "keep working hard."
"Everything's gonna work out and it always does," she shared.
Rodrigo dropped her sophomore album, Guts, earlier this month. The album's debut was preceded by three single releases, including the June release of "Vampire," the first song off the album. The single made waves after fans speculated the track is about her ex, Zack Bia. The DJ reacted to the speculation in an interview with GQ, admitting that he doesn't think the song is actually about him.
"I don't think it's really about me," Bia told the magazine. "I think the Internet just ran with it."
Bia conceded that he might be one part of a fictional composite character, stating, "Look, I’m in the industry so I know how a song gets made," he said, firmly denying that their relationship was worth a breakup song. "We hung out, we're both busy, and we ended up not furthering our relationship. There was never any drama, you know?"
Furthermore, Bia expressed his admiration for "Vampire," describing it as a hit. "The song's so big and so awesome," he tells GQ. "Look, a heartbreak song for the summertime, it’s an undefeated formula."
Rodrigo's music has often sparked interest in her love life. Much of her debut album was rumored to be about her failed romance with High School Musical: The Musical: The Series co-star, Joshua Bassett. In 2021, she was said to be dating 26-year-old producer Adam Faze, but the two split in early 2022. She was later linked to Bia. They called it quits in August 2022.
In an interview for Vogue's August issue, Rodrigo reflected on growing up in the spotlight and grappling with the public's interest in her relationships.
"It's an interesting thing to think about," she said. "I understand it. I could sit here and be like, 'I don't get why people do that,' but I do it so often."
She described the full-length Guts album as being "about figuring stuff out, about failures and successes and making mistakes," declining to elaborate further on said mistakes.
"You'll have to listen to the rest of the album," she said with a laugh.