21 for 21: Olivia Rodrigo’s most memorable moments (so far)

As the Grammy-winning star turns 21, we're counting down her strongest performances and sharpest tracks

Music Features Olivia Rodrigo
21 for 21: Olivia Rodrigo’s most memorable moments (so far)
Olivia Rodrigo performs at the 2022 Grammy Awards; Olivia Rodrigo performs at the 2021 Brit Awards Image: Kevin Mazur/Getty Images for The Recording Academy; JMEnternational/JMEnternational for BRIT Awards/Getty Images

Over the course of three short years, Olivia Rodrigo emerged as one of the defining pop stars of the 2020s. Shortly after the melancholy “Drivers License” became a viral sensation in 2021, Rodrigo’s debut album Sour became the rarest of things: an album rooted in classic pop-rock traditions that felt startlingly fresh due to her sharply defined personality.

Sour became a commercial and critical hit, earning three Grammys in the process. Last year’s Guts may not have won any Grammys, but in every other respect it matched its predecessor. The single “Vampire” topped the chart and was a critics favorite: Robert Christgau, the Dean of American Rock Critics, placed it number one on his Best Of 2023 list.

Guts suggests that Rodrigo has a long career ahead of her but she already has plenty of memorable events in her rear view mirror. In celebration of her 21st birthday, here are 21 defining moments in Rodrigo’s supernova of a career.

previous arrow19. iHeartRadio Festival Las Vegas (2021) next arrow
Olivia Rodrigo at the iHeartRadio music festival 2021 full performance

The first concert Rodrigo performed for Sour happened at the iHeartRadio Music Festival in Las Vegas September 2021. It was a brief set—only five songs, opening with “Brutal” and closing with “Good 4 U”—that served as a bracing notice of the arrival of a savvy pop star.

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