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

As part of Carly Simon’s induction into the Rock & Roll Hall of Fame in 2022, Olivia Rodrigo sang the songwriter’s biggest hit, “You’re So Vain.” Rodrigo’s laconic phrasing brought out the cynical edge in the song and undercut the polish of the house band’s overheated arrangement.

Unveiled the week that Guts was released, this live from rehearsal version of “All-American Bitch” emphasized the snarl of the album’s opening track. Pogoing with the beat and culminating in a powerful shriek, Rodrigo throws herself into the song’s defiant attitude.

The gimmick for Olivia Rodrigo’s 2021 appearance on NPR’s Tiny Desk Concert—then dubbed Tiny Desk (Home) Concerts due to COVID-19 pandemic restrictions—was to have the singer of “Drivers License” play at a DMV. It was clever and picturesque, plus it lent itself to stripped down performances that showcased the emotional thrust of four choice songs from Sour, including “Traitor” and “Good 4 U.”

Premiered on YouTube in June 2021, right in the thick of COVID-19, Sour Prom was designed as a short film to tide over fans until Olivia Rodrigo was able to hit the road. Too florid to be considered a concert film, Sour Prom nevertheless featured live performances, the raw edge of Rodrigo’s voice nicely contrasting with the high school dance setting.

Olivia Rodrigo’s first major appearance on an American awards show arrived at the . Entering on a glitter ball, Rodrigo prowled the stage as she snarled “Good 4 U,” and she remained the focus of energy even when surrounded by dancers and hyperactive stage show … until Rodrigo deliberately took herself out of view by smashing the camera lens at the end of the song.

On a night she won three statuettes—including Best New Artist and Best Pop Vocal Album for Sour—Olivia Rodrigo stole the show at the 64th Annual Grammys with a dramatic rendition of “Drivers License,” the song that snagged her a Grammy for Best Pop Solo Performance. Rodrigo’s intensity transcended the literal staging of placing her in front of the car; her emotions cut through any suggestion of corniness.

Olivia Rodrigo may have gone home empty handed at the 66th Annual Grammys, but she delivered one of the most memorable performances of the evening with a heightened rendition of her melodramatic masterpiece “Vampire.” Performing in front of a backdrop featuring flowers that slowly started bleeding—she wound up mimicking the bloodletting by scratching her cheek—Rodrigo brought her goth undertones to the forefront in a bewitching fashion.

A key stop on the promo campaign for her sophomore set Guts, Olivia Rodrigo held a surprise concert on the night of October 9, 2023 at the Theatre at the Ace Hotel in downtown Los Angeles. Over the course of an hour, Rodrigo ran through many of the album’s pivotal songs, often with the assistance of her collaborator Dan Nigro. This wasn’t a full-blown production—no drums, no lights, no electric guitars—but the intimate setting highlights her songcraft and allows Rodrigo’s charm to shine through.

Pushing “Vampire” on almost every show, Olivia Rodrigo took a different tactic when she returned to Jimmy Kimmel Live!, opting to play the nervy ’90s salute “Ballad of a Homeschooled Girl” instead. In many ways, this song indicated what Guts had to offer better than the lead single: it mashed up styles and rhythms, brought together by Rodrigo’s clever wordplay and charisma.

Sour mania spread to Washington D.C. in July 2021. Looking to rally the public around COVID-19 safety measures, the White House administration invited Olivia Rodrigo to meet with President Joe Biden, Vice President Kamala Harris, and Chief Medical Advisor Dr. Anthony Fauci, all in hopes of shoring up vaccination rates among the youth. It was a photo-op reminiscent of the time Richard Nixon invited Elvis Presley to the White House to discuss the singer’s desire to be made a “Federal Agent-at-Large” on the war against drugs.

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.

The slow-burning “Drivers License” didn’t quite prepare listeners for what Olivia Rodrigo’s debut album Sour delivered. Anchored in the adolescent angst “Drivers License” so expertly articulated, Sour also showed a sense of stylistic daring and melodic invention. Rodrigo nodded to some of her idols—the pounding opener “Brutal” flipped a thumping riff reminiscent of Elvis Costello’s “Pump it Up,” much to the delight of the old punk rocker—but the striking thing about Sour is that the hooks and emotions all seemed fresh due to her perspective. Smart, sensitive and nervy, playing with the past but not indebted to it, Olivia Rodrigo comes across as a fully-formed 21st century icon on this bracing debut.