Olivia Rodrigo Performs ‘If It Makes You Happy’ With Sheryl Crow, Debuts ‘Lacy’ & ‘Making the Bed’ Live

Six years before Olivia Rodrigo was born, Sheryl Crow‘s “If It Makes You Happy” was charting in the top 10 of the Billboard Hot 100. Decades later, the hit singer-songwriters got together at Nashville’s Bluebird Cafe for a duet of Crow’s ’90s hit.

“pinch me! sang one of my favorite songs of all time with the greatest of all time @sherylcrow !!!! what an honor!!!!” Rodrigo wrote on Instagram, where she shared a photo with Crow and a video of their “If It Makes You Happy” performance, on Friday night (Sept. 29).

“Funnest day ever with the amazingly brilliant @oliviarodrigo! What a talent!! And the loveliest young woman!” Crow said, sharing Rodrigo’s post on her Instagram page.

A video shows the pair harmonizing on the chorus: “If it makes you happy/ It can’t be that bad/ If it makes you happy/ Then why the hell are you so sad?”

Rodrigo, guitar in hand, also performed the Guts ballad “Lacy” live for the first time during her appearance at the Bluebird Cafe, as well as the album’s lead single “Vampire” on piano. She also debuted “Making the Bed” (also from Guts) live on piano.

Crow and Rodrigo connected last year at Billboard‘s 2022 Women in Music event, where Rodrigo was presented Woman of the Year by Crow, who praised the example Rodrigo is setting for her generation of artists. “When I came up, women were struggling to be the architects of their own careers,” she said. “So when I see someone like our Woman of the Year Olivia Rodrigo having such incredible success at such an early age, I am blown away.”

“I am such a massive fan of you and your songwriting,” Rodrigo gushed at the time. She noted, “It’s not always easy being a young woman in the music industry, but I’ve found so much strength from the female songwriters who have come before me and paved the way and opened doors for so many young women like me.”

See clips from Rodrigo’s Bluebird Cafe set below.