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

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.

2. Guts (2023)

A perfect sequel to a thrilling debut, Guts proved Olivia Rodrigo not only was no flash in the pan but that her gifts are maturing at a rapid rate. Working from the same basic template as Sour—the atmospheric soul-searching is countered by coiled punk rock—Rodrigo digs deeper, filling Guts with barbed quips and bleeding-heart emotions, all sharpened by her melodic writing. The complexity of emotion, the sturdiness of the songs and, especially, the playfulness of the rockers, like the album opener “All-American Bitch,” suggests that Rodridgo has the brains and crafts that will serve her well in the long haul.