\u2018Ballad of a Homeschooled Girl\u2019<\/h2>\n\n\t\t\t![\"LOS](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/GettyImages-1439463036crop.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Jeff Kravitz\/FilmMagic\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tA sensitive account of the social anxiety that can get left over from the isolation of her home-schooling days\u2014not to mention a clever salute to Bob Dylan, one of her songwriting idols, who inspired her with \u201cBallad of a Thin Man.\u201d The glitch is the unfortunate chorus \u201csocial suicide,\u201d a klutzy line that doesn\u2019t work as a hook or a joke at all, and gets in the way of the song living up to the title\u2019s promise. As for Olivia singing \u201cevery guy I like is gay\u201d? Best-case scenario.<\/p>\n
\n\tBest line:<\/strong> \u201cI\u2019m on the outside of the greatest inside joke.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u20181 Step Forward, 3 Steps Back\u2019<\/h2>\n\n\t\t\t![\"LAS](\"https:\/\/www.rollingstone.com\/wp-content\/themes\/vip\/pmc-rollingstone-2022\/assets\/public\/lazyload-fallback.gif\")
![\"LAS](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/GettyImages-1341181013.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Kevin Mazur\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tOlivia interpolates the 2017 Taylor Swift classic \u201cNew Year\u2019s Day,\u201d from Reputation<\/em>. A haunting and powerful chronicle of a bad romance. She realizes it\u2019s time for her to step off this emotional roller coaster, while she\u2019s got the chance. But it\u2019s difficult, because \u201cthe roller coaster\u2019s all I\u2019ve ever had.\u201d The day after she wrote this song, the dude dumped her. Good riddance.<\/p>\n\n\tBest line: \u201cLike, am I pretty? Am I fun, boy? I hate that I give you power over that kinda stuff.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n
- \n
\n\u2018Friday I\u2019m In Love\u2019 (with Robert Smith)<\/h2>\n\n\t\t\t![\"GLASTONBURY,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-robert-smith.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Kevin Mazur\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tO-Rod was the hit of last summer\u2019s Glastonbury Festival, but she really sealed the deal when she brought out a local hero. \u201cHe\u2019s probably the best songwriter to come out of England!\u201d she announced, as The Cure\u2019s Robert Smith ambled onstage. The whole world was stunned by the sight of the goth elder grinning from ear to ear\u2014not something you see every day\u2014as he sang a couple of Cure classics with her, including the 1992 hit \u201cFriday I\u2019m In Love.\u201d They preserved their duet on a stand-alone vinyl single as well as her essential Live at Glastonbury <\/em>album. In the liner notes, Liv called her set \u201cthe most exhilarating 90 minutes of my life.\u201d\u00a0<\/p>\n\n\tBest line:<\/strong> \u201cAlways take a big bite\/It\u2019s such a gorgeous sight\/To see you eat in the middle of the night.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Expectations\u2019<\/h2>\n\n\t\t\t![\"CHICAGO,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-expectations.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Natasha Moustache\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tNear the end of You Seem Pretty Sad for a Girl So in Love<\/em>, she tries to move on, cruising the bars of Silverlake looking for her next Mr. Bad Idea Right? She vows, \u201cPast mistakes are just new information.\u201d (Speaking of mistakes: pop stars complaining about people with \u201cfake jobs\u201d\u2026 in 2026? In a chorus?<\/em> A sign of how fast she was rushing to crank out those final songs.) The Eighties production has a camp touch with the robot-boy vocal choir, in the style of Madonna\u2019s \u201cMaterial Girl\u201d or Lene Lovich\u2019s \u201cNew Toy.\u201d\u00a0<\/p>\n\n\tBest line:<\/strong> \u201cSo I hit the new year like a single girl at a Vegas bar\/Rocking my minidress with a vodka cran and an open heart.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018River\u2019<\/h2>\n\n\t\t\t![\"on](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-river.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Griffin Lotz for Rolling Stone\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tAn early sign of Olivia\u2019s flair for cover versions, from one of the funniest-titled Christmas albums ever: High School Musical: The Musical: The Holiday Special: The Soundtrack<\/em>. Liv gives a taste of things to come by singing Joni Mitchell\u2019s Blue<\/em> classic about a bummed-out December, feeling weak in the knees. It\u2019s got a whole new resonance now after You Seem Pretty Sad<\/em>, since \u201cRiver\u201d sounds like the template for her new break-up songs. (Yes, I said in the intro that HSM<\/em> songs don\u2019t count, but I guess this is cheating, and I\u2019m still a traitor.)<\/p>\n\n\tBest line:<\/strong> \u201cI\u2019m selfish and I\u2019m sad.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018The Book of Love\u2019<\/h2>\n\n\t\t\t![\"CHICAGO,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-book-of-love.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Barry Brecheisen\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tA charity song for the 2026 War Child benefit compilation Help (2)<\/em>. Olivia sings the modern-day wedding standard from the Magnetic Fields\u2019 master tunesmith Stephen Merritt, made famous by Peter Gabriel. She called it \u201cone of my fav songs ever.\u201d<\/p>\n\n\tBest line:<\/strong> \u201cThe book of love is long and boring\/No one can lift the damn thing.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Say It Ain\u2019t So\u2019 (with Weezer)<\/h2>\n\n\t\t\t![\"CHICAGO,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-say-it-aint-so.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Erika Goldring\/WireImage\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tWhen Olivia headlined Lollapalooza in Chicago, she brought out a surprise guest: her childhood heroes Weezer, the very first band she saw in concert as a little girl. (She was born in between \u201cDope Nose\u201d and \u201cBeverly Hills.\u201d) They played two Blue Album <\/em>bangers that she released as a vinyl 7-inch, turning \u201cSay It Ain\u2019t So\u201d into a cross-generational pop-punk full-circle moment.<\/p>\n\n\tBest line: <\/strong>\u201cLike father, stepfather, this son is drowning in the flood.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Buddy Holly\u2019 (with Weezer)<\/h2>\n\n\t\t\t![\"CHICAGO,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-say-buddy-holly.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Joshua Applegate\/WireImage\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tBut the next song was even better, as she sang, \u201cI look just like Buddy Holly and you\u2019re Mary Tyler Moore!\u201d (One of her power moves, when it comes to cover versions: she never changes the pronouns or gender roles. Always the way to do it.) Olivia singing \u201cyou need a guardian\u201d to Rivers Cuomo\u2014was she wrong? A reminder that she makes such a brilliant pop star because she\u2019s a brilliant pop fan, first and foremost.\u00a0<\/p>\n
\n\tBest line:<\/strong> \u201cWhat\u2019s with these homies dissing my girl?\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018All I Want\u2019<\/h2>\n\n\t\t\t![\"CHICAGO,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-all-i-want.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Josh Brasted\/FilmMagic\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tTechnically a High School Musical <\/em>song, but it makes the cut since (1) she wrote it by herself and (2) she still occasionally does it live, which makes it canon. What could be a realer 16-year-old lyric than \u201cI miss the days when I was young and naive\u201d?<\/p>\n\n\tBest line:<\/strong> \u201cAll I have is myself at the end of the day\/And all I want is for that to be okay.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Stick Season\u2019<\/h2>\n\n\t\t\t![\"NEW](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-stick-season.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Kevin Mazur\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tA limited-edition single for Record Store Day \u2014 Olivia and Noah Kahan interpret each other\u2019s tunes, recorded in the BBC Radio 1 Live Lounge. She sings \u201cStick Season,\u201d while Noah sings \u201cLacy\u201d on the flip side \u2014 beautifully proving they\u2019re mutual fans who\u2019ve listened close to each other\u2019s voices. They also sang this together onstage<\/a> at her Madison Square Garden show; she\u2019s called it one of her favorite concert moments.<\/p>\n\n\tBest line: <\/strong>\u201cNow I\u2019m terrified of weather \u2018cause I see you when it rains.\u201d<\/p>\n\n\t\\<\/p>\n<\/div>\n<\/article>\n<\/li>\n
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\n\u2018Cigarette Smoke\u2019<\/h2>\n\n\t\t\t![\"on](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-cigarette-smoke.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Griffin Lotz for Rolling Stone\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tThe morose finale of You Seem Pretty Sad<\/em> \u2014 she resists the temptation to give a tidy ending to the story, or to wrap it up with a bow, instead choosing to let it all hang out with a stream of chaotic, messy, vague, hit-or-miss images, dashed out in haste while the break-up pain is still fresh. (Including an out-of-nowhere \u201cher\u201d that probably wouldn\u2019t have survived a second draft.) The beautifully muted arrangement covers up the glitches, making it work as a mood piece.\u00a0<\/p>\n\n\tBest line: <\/strong>\u201cIt\u2019s a real quiet house with the shower left on\/Five beers in the fridge and the second car\u2019s gone.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Burning Down the House\u2019 (with David Byrne)<\/h2>\n\n\t\t\t![\"Olivia](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2025\/08\/legend-collabs-olivia-david-byrne.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Griffin Lotz for Rolling Stone\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tAll through her awesome summer-2025 tour<\/a>, Olivia kept inviting her heroes up onstage, but she outdid herself at New York\u2019s Governors Ball. Qu\u2019est-ce sue c\u2019est?<\/em> David Byrne, who joined her for a jubilant duet on the Talking Heads\u2019 1983 space-funk classic \u201cBurning Down the House.\u201d She released it as a vinyl single, along with Byrne\u2019s Fear of Music<\/em>-style version of \u201cDrivers License.\u201d (So\u2026the rest of the Sour<\/em> covers project? Is that still even happening? David would probably cover the whole album if she asked.) OliviByrne were definitely making flippy-floppy, trading their best moves in a long, touching, and hilarious dance-off. Note: Byrne wasn\u2019t the only New York CBGB punk legend she honored at Gov Ball. Her encore ensemble was a tribute to Blondie\u2019s Debbie Harry, who wore the same outfit for her famous 1976 Punk<\/em> magazine photo session.<\/p>\n\n\tBest line: <\/strong>\u201cStrange, but not a stranger.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Hope Ur Ok\u2019<\/h2>\n\n\t\t\t![\"LONDON,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/GettyImages-1317499302crop.jpg?w=300\")
\n\t\t\t\t\tImage Credit: JMEnternational for BRIT Awards\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tOlivia taps into the same empathetic spirit of Fiona Apple\u2019s \u201cShameika\u201d on Fetch The Bolt Cutters<\/em>, or Taylor Swift\u2019s \u201cSeven\u201d on Folklore<\/em> \u2014 living with the complex memory of a childhood friend. She sings about queer kids getting rejected by their families, and tells them long-distance, \u201cI hope you know how proud I am that you were created\/With the courage to unlearn all of their hatred.\u201d Believe it or not, not so long ago (like, oh, let\u2019s say the entire freaking 20th century<\/em>), hearing words like this from a teen pop star would have been totally unthinkable.\u00a0<\/p>\n\n\tBest line: <\/strong>\u201cAddress the letters to the holes in my butterfly wings.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Traitor\u2019<\/h2>\n\n\t\t\t![\"'Traitor'](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/traitor-copy.jpg?w=300\")
\t\t\t\t\t<\/figure>\n\t<\/p>\n
\n\n\t\u201cIt took you two weeks to go and date her\/Guess you didn\u2019t cheat, but you\u2019re still a traitor.\u201d Your honor, the prosecution rests.\u00a0<\/p>\n
\n\tBest line: <\/strong>\u201cWhile she\u2019s sleeping in the bed we made\/Don\u2019t you dare forget about the way you betrayed me.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Just Like Heaven\u2019 (with Robert Smith)<\/h2>\n\n\t\t\t![\"Olivia](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/04\/olivia-rodrigo-robert-smith.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Samir Hussein\/WireImage\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tDo you get deja vu? The best of her live-cover singles, with Robert Smith joining her for one of the Eighties\u2019 saddest songs \u2014 while she wore a T-shirt saying, \u201cYou Know All The Words to \u2018Just Like Heaven.\u2019\u201d (It would take nearly a year for the world to figure out that reference.) She\u2019s a lifelong Cure superfan \u2014 who can forget the footage of teen Liv in the car belting \u201cBoys Don\u2019t Cry\u201d? After they sang this duet, she posted a photo of them backstage downing shots \u2014 that\u2019s so American of her. Robert Smith, we\u2019ll meet again \u2014 higher up on this list.<\/p>\n
\n\tBest line:<\/strong> \u201cSpinning on that dizzy edge\/Kissed her face and kissed her head.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018My Way\u2019<\/h2>\n\n\t\t\t![\"LOS](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-say-my-way.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Amy Sussman\/WireImage\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\t\u201cHere\u2019s the part where the girl gets pissed,\u201d indeed. Olivia goes off on a hilarious rant against a suspected rival, the only time on Pretty Sad <\/em>she shows her OliviAggro fangs, and it\u2019s the closest she comes to a pop-punk snarler, despite the excellent synth-pop buzz. \u201cMy Way\u201d is deliciously petty, self-mocking, irresponsible, and misogynistic, in the \u201cMisery Business\u201d\/\u201cBetter Than Revenge\u201d tradition. But given how much Olivia worships Blondie, her role model sounds like it must be Debbie Harry\u2019s sneer in \u201cRip Her To Shreds.\u201d <\/a>Fun fact: the most famous cover version of Frank Sinatra\u2019s \u201cMy Way\u201d is the punk makeover <\/a>from the Sex Pistols\u2019 Sid Vicious. In the biopic Pistol<\/em>, it\u2019s sung by the actor playing Sid: Louis Partridge. <\/p>\n\n\tBest line: <\/strong>\u201cMaybe I\u2019m a petty bitch, but you made me resort to this! That\u2019s it! I win!\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Jealousy Jealousy\u2019<\/h2>\n\n\t\t\t![\"LOS](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/GettyImages-1357181988crop.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Matt Winkelmeyer\/Getty Images for Variety\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tOlivia sings about the kind of compare-and-despair self-loathing that <\/strong>results from excessive phone addiction. She sings about it with all her typical sympathy and wit, especially when she\u2019s scrolling through \u201ccool vintage clothes and vacation photos.\u201d Plus one of her first killer bridges. The studio version is stiff, but \u201cJealousy, Jealousy\u201d really took off as one of her live hell-raisers, with a punked-out Clash-style attack, as she chants, \u201cCo-comparison is killing me slowly.\u201d<\/p>\n\n\tBest line: <\/strong>\u201cA pretty face, a pretty boyfriend too\/I wanna be you so bad and I don\u2019t even know you.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Less\u2019<\/h2>\n\n\t\t\t![\"ROSKILDE,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-less.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Didier Messens\/Redferns\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tA torchy change-of-pace piano weeper in cocktail mode, mourning the burnout of a relationship, including a failed getaway to Big Sur. Who among us HASN\u2019T broken down in a crying fit on the curb at LAX?\u00a0<\/p>\n
\n\tBest line: <\/strong>\u201cMaybe I\u2019m a stubborn overthinker, but I\u2019ve been thinking over this a lot.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Making the Bed\u2019<\/h2>\n\n\t\t\t![\"BEVERLY](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/GettyImages-1473119439.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Cindy Ord\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tA moving confession about growing up, maybe even getting famous, from the POV of a hyper-responsible only child and Disney starlet. She got what she wanted, but she doesn\u2019t like who she\u2019s turning into, always pretending she\u2019s older than she is. \u201cGetting drunk at a club with my fair-weather friends,\u201d she sighs. \u201cPush away all the people who know me the best\/But it\u2019s me who\u2019s been making the bed.\u201d\u00a0<\/p>\n
\n\tBest line:<\/strong> \u201cI tell someone I love them, just as a distraction\/And they tell me that they love me like I\u2019m some tourist attraction.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Never Do\u2019<\/h2>\n\n\t\t\t![\"CHICAGO,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-never-do.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Erika Goldring\/WireImage\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tA skeletal demo of a song written after her third album was turned in, released as vinyl-collector bait on the flip side of \u201cThe Cure,\u201d but a very different story about a generic cad. The guy in \u201cThe Cure\u201d tries hard to suck out her toxins, but this guy isn\u2019t trying at all, leaving her to wonder, \u201cNaked in your bed\/Baby, where have you been?\u201d\u00a0<\/p>\n
\n\tBest line:<\/strong> \u201cWe both do our best\/It\u2019s a shame that my best is much more.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018The Grudge\u2019<\/h2>\n\n\t\t\t![\"LOS](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/GettyImages-1532113988.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Emma McIntyre\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tShe talks tough to an ex \u2014 but only after their break-up, as she rehashes their old arguments in front of her bedroom mirror. \u201cI was just driving to the studio,\u201d Olivia once said. \u201cAnd I was listening to the Smiths and there\u2019s this lyric [in \u2018I Know It\u2019s Over\u2019] where he says, \u2018It takes courage to be kind.\u2019 I was really upset at the time and I was like, \u2018What if I don\u2019t what to have courage and what if I don\u2019t want to be kind?\u2019\u201d She wrote the lyrics at the next stoplight: \u201cIt takes strength to forgive, but I don\u2019t feel strong.\u201d<\/p>\n
\n\tBest line: <\/strong>\u201cHurt people hurt people\/We both drew blood, but man, those cuts were never equal.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Can\u2019t Catch Me Now\u2019<\/h2>\n\n\t\t\t![\"Olivia](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-cant-catch-me-now.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Christopher Polk\/Billboard\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tHer great soundtrack theme for The Hunger Games: The Ballad of Songbirds & Snakes<\/em>. It fits the pastoral acoustic folk-horror mode of the franchise \u2014 definitely cut from the same cloth as Taylor Swift\u2019s \u201cSafe and Sound\u201d with the Civil Wars. She sings from the perspective of the heroine Lucy Gray, but she puts her own stamp on it. It\u2019s yet another Olivia song about an older man who planned on picking her up and tossing her away, only to find that she still haunts him long after she escapes.<\/p>\n\n\tBest line: \u201cI bet you figured I\u2019d pass like winter\/Be something easy to forget.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n
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\n\u2018Pretty Isn\u2019t Pretty\u2019<\/h2>\n\n\t\t\t![\"TODAY](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/GettyImages-1653671780.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Kara Birnbaum\/NBC\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tA powerfully candid tale of negative body image and torturously low self-esteem. It\u2019s almost a foretaste of \u201cThe Cure,\u201d dissecting the destructive thoughts that can prey on an insecure young mind, as she laments, \u201cI bought all the clothes that they told me to buy\/I chased some ideal my whole fucking life.\u201d The heavily flanged guitar is very 1985, a clever sign of producer Dan Nigro\u2019s ever-fruitful Eighties inspiration.<\/p>\n
\n\tBest line: <\/strong>\u201cIt\u2019s in my phone, it\u2019s in my head, it\u2019s in the boys I bring to bed.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Scared of My Guitar\u2019<\/h2>\n\n\t\t\t![\"BARCELONA,](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2026\/06\/olivia-rodrigo-scared-of-my-guitar.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Xavi Torrent\/Getty Images\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tShe can lie to everybody else about her feelings \u2014 even the boy in her arms, who she doesn\u2019t really love. But this girl can\u2019t fool her guitar, because it knows all her secrets and gives her the truth. (\u201cYou can tell your guitar things that you can\u2019t tell people,\u201d as Paul McCartney once told Rolling Stone<\/em>. \u201cAnd it will answer you with things people can\u2019t tell you.\u201d) It\u2019s a muted acoustic ballad with some Ladies of the Canyon<\/em> swoops in her vocal.\u00a0<\/p>\n\n\tBest line: <\/strong>\u201cI\u2019m so scared of my guitar\/Because it cuts right to the heart\/It knows me too well, so I got no excuse\/I can\u2019t lie to it the same way that I lie to you.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n- \n
\n\u2018Teenage Dream\u2019<\/h2>\n\n\t\t\t![\"Olivia](\"https:\/\/www.rollingstone.com\/wp-content\/uploads\/2023\/09\/olivia_rodrigo_PDX_31.jpg?w=300\")
\n\t\t\t\t\tImage Credit: Samuel Gehrke for Rolling Stone\t\t\t\t<\/figcaption><\/figure>\n\t<\/p>\n
\n\n\tThe massive finale of Guts, <\/em>a piano confession building to the climactic lighters-up chorus. Olivia blows out the candles as she turns 20, singing, \u201cI\u2019m sorry that I couldn\u2019t always be your teenage dream.\u201d (Three years after she sang \u201cI\u2019m so sick of 17\/Where\u2019s my fucking teenage dream?\u201d) <\/strong>But she\u2019s got tough questions for the future, asking, \u201cWhen am I gonna stop being wise beyond my years? And just start being wise? When am I gonna stop being a pretty young thing to guys?\u201d\u00a0<\/p>\n
\t<\/p>\n
\n\tA sensitive account of the social anxiety that can get left over from the isolation of her home-schooling days\u2014not to mention a clever salute to Bob Dylan, one of her songwriting idols, who inspired her with \u201cBallad of a Thin Man.\u201d The glitch is the unfortunate chorus \u201csocial suicide,\u201d a klutzy line that doesn\u2019t work as a hook or a joke at all, and gets in the way of the song living up to the title\u2019s promise. As for Olivia singing \u201cevery guy I like is gay\u201d? Best-case scenario.<\/p>\n
\n\tBest line:<\/strong> \u201cI\u2019m on the outside of the greatest inside joke.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tOlivia interpolates the 2017 Taylor Swift classic \u201cNew Year\u2019s Day,\u201d from Reputation<\/em>. A haunting and powerful chronicle of a bad romance. She realizes it\u2019s time for her to step off this emotional roller coaster, while she\u2019s got the chance. But it\u2019s difficult, because \u201cthe roller coaster\u2019s all I\u2019ve ever had.\u201d The day after she wrote this song, the dude dumped her. Good riddance.<\/p>\n \n\tBest line: \u201cLike, am I pretty? Am I fun, boy? I hate that I give you power over that kinda stuff.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tO-Rod was the hit of last summer\u2019s Glastonbury Festival, but she really sealed the deal when she brought out a local hero. \u201cHe\u2019s probably the best songwriter to come out of England!\u201d she announced, as The Cure\u2019s Robert Smith ambled onstage. The whole world was stunned by the sight of the goth elder grinning from ear to ear\u2014not something you see every day\u2014as he sang a couple of Cure classics with her, including the 1992 hit \u201cFriday I\u2019m In Love.\u201d They preserved their duet on a stand-alone vinyl single as well as her essential Live at Glastonbury <\/em>album. In the liner notes, Liv called her set \u201cthe most exhilarating 90 minutes of my life.\u201d\u00a0<\/p>\n \n\tBest line:<\/strong> \u201cAlways take a big bite\/It\u2019s such a gorgeous sight\/To see you eat in the middle of the night.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tNear the end of You Seem Pretty Sad for a Girl So in Love<\/em>, she tries to move on, cruising the bars of Silverlake looking for her next Mr. Bad Idea Right? She vows, \u201cPast mistakes are just new information.\u201d (Speaking of mistakes: pop stars complaining about people with \u201cfake jobs\u201d\u2026 in 2026? In a chorus?<\/em> A sign of how fast she was rushing to crank out those final songs.) The Eighties production has a camp touch with the robot-boy vocal choir, in the style of Madonna\u2019s \u201cMaterial Girl\u201d or Lene Lovich\u2019s \u201cNew Toy.\u201d\u00a0<\/p>\n \n\tBest line:<\/strong> \u201cSo I hit the new year like a single girl at a Vegas bar\/Rocking my minidress with a vodka cran and an open heart.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tAn early sign of Olivia\u2019s flair for cover versions, from one of the funniest-titled Christmas albums ever: High School Musical: The Musical: The Holiday Special: The Soundtrack<\/em>. Liv gives a taste of things to come by singing Joni Mitchell\u2019s Blue<\/em> classic about a bummed-out December, feeling weak in the knees. It\u2019s got a whole new resonance now after You Seem Pretty Sad<\/em>, since \u201cRiver\u201d sounds like the template for her new break-up songs. (Yes, I said in the intro that HSM<\/em> songs don\u2019t count, but I guess this is cheating, and I\u2019m still a traitor.)<\/p>\n \n\tBest line:<\/strong> \u201cI\u2019m selfish and I\u2019m sad.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tA charity song for the 2026 War Child benefit compilation Help (2)<\/em>. Olivia sings the modern-day wedding standard from the Magnetic Fields\u2019 master tunesmith Stephen Merritt, made famous by Peter Gabriel. She called it \u201cone of my fav songs ever.\u201d<\/p>\n \n\tBest line:<\/strong> \u201cThe book of love is long and boring\/No one can lift the damn thing.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tWhen Olivia headlined Lollapalooza in Chicago, she brought out a surprise guest: her childhood heroes Weezer, the very first band she saw in concert as a little girl. (She was born in between \u201cDope Nose\u201d and \u201cBeverly Hills.\u201d) They played two Blue Album <\/em>bangers that she released as a vinyl 7-inch, turning \u201cSay It Ain\u2019t So\u201d into a cross-generational pop-punk full-circle moment.<\/p>\n \n\tBest line: <\/strong>\u201cLike father, stepfather, this son is drowning in the flood.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tBut the next song was even better, as she sang, \u201cI look just like Buddy Holly and you\u2019re Mary Tyler Moore!\u201d (One of her power moves, when it comes to cover versions: she never changes the pronouns or gender roles. Always the way to do it.) Olivia singing \u201cyou need a guardian\u201d to Rivers Cuomo\u2014was she wrong? A reminder that she makes such a brilliant pop star because she\u2019s a brilliant pop fan, first and foremost.\u00a0<\/p>\n \n\tBest line:<\/strong> \u201cWhat\u2019s with these homies dissing my girl?\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tTechnically a High School Musical <\/em>song, but it makes the cut since (1) she wrote it by herself and (2) she still occasionally does it live, which makes it canon. What could be a realer 16-year-old lyric than \u201cI miss the days when I was young and naive\u201d?<\/p>\n \n\tBest line:<\/strong> \u201cAll I have is myself at the end of the day\/And all I want is for that to be okay.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tA limited-edition single for Record Store Day \u2014 Olivia and Noah Kahan interpret each other\u2019s tunes, recorded in the BBC Radio 1 Live Lounge. She sings \u201cStick Season,\u201d while Noah sings \u201cLacy\u201d on the flip side \u2014 beautifully proving they\u2019re mutual fans who\u2019ve listened close to each other\u2019s voices. They also sang this together onstage<\/a> at her Madison Square Garden show; she\u2019s called it one of her favorite concert moments.<\/p>\n \n\tBest line: <\/strong>\u201cNow I\u2019m terrified of weather \u2018cause I see you when it rains.\u201d<\/p>\n \n\t\\<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tThe morose finale of You Seem Pretty Sad<\/em> \u2014 she resists the temptation to give a tidy ending to the story, or to wrap it up with a bow, instead choosing to let it all hang out with a stream of chaotic, messy, vague, hit-or-miss images, dashed out in haste while the break-up pain is still fresh. (Including an out-of-nowhere \u201cher\u201d that probably wouldn\u2019t have survived a second draft.) The beautifully muted arrangement covers up the glitches, making it work as a mood piece.\u00a0<\/p>\n \n\tBest line: <\/strong>\u201cIt\u2019s a real quiet house with the shower left on\/Five beers in the fridge and the second car\u2019s gone.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tAll through her awesome summer-2025 tour<\/a>, Olivia kept inviting her heroes up onstage, but she outdid herself at New York\u2019s Governors Ball. Qu\u2019est-ce sue c\u2019est?<\/em> David Byrne, who joined her for a jubilant duet on the Talking Heads\u2019 1983 space-funk classic \u201cBurning Down the House.\u201d She released it as a vinyl single, along with Byrne\u2019s Fear of Music<\/em>-style version of \u201cDrivers License.\u201d (So\u2026the rest of the Sour<\/em> covers project? Is that still even happening? David would probably cover the whole album if she asked.) OliviByrne were definitely making flippy-floppy, trading their best moves in a long, touching, and hilarious dance-off. Note: Byrne wasn\u2019t the only New York CBGB punk legend she honored at Gov Ball. Her encore ensemble was a tribute to Blondie\u2019s Debbie Harry, who wore the same outfit for her famous 1976 Punk<\/em> magazine photo session.<\/p>\n \n\tBest line: <\/strong>\u201cStrange, but not a stranger.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tOlivia taps into the same empathetic spirit of Fiona Apple\u2019s \u201cShameika\u201d on Fetch The Bolt Cutters<\/em>, or Taylor Swift\u2019s \u201cSeven\u201d on Folklore<\/em> \u2014 living with the complex memory of a childhood friend. She sings about queer kids getting rejected by their families, and tells them long-distance, \u201cI hope you know how proud I am that you were created\/With the courage to unlearn all of their hatred.\u201d Believe it or not, not so long ago (like, oh, let\u2019s say the entire freaking 20th century<\/em>), hearing words like this from a teen pop star would have been totally unthinkable.\u00a0<\/p>\n \n\tBest line: <\/strong>\u201cAddress the letters to the holes in my butterfly wings.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\t\u201cIt took you two weeks to go and date her\/Guess you didn\u2019t cheat, but you\u2019re still a traitor.\u201d Your honor, the prosecution rests.\u00a0<\/p>\n \n\tBest line: <\/strong>\u201cWhile she\u2019s sleeping in the bed we made\/Don\u2019t you dare forget about the way you betrayed me.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tDo you get deja vu? The best of her live-cover singles, with Robert Smith joining her for one of the Eighties\u2019 saddest songs \u2014 while she wore a T-shirt saying, \u201cYou Know All The Words to \u2018Just Like Heaven.\u2019\u201d (It would take nearly a year for the world to figure out that reference.) She\u2019s a lifelong Cure superfan \u2014 who can forget the footage of teen Liv in the car belting \u201cBoys Don\u2019t Cry\u201d? After they sang this duet, she posted a photo of them backstage downing shots \u2014 that\u2019s so American of her. Robert Smith, we\u2019ll meet again \u2014 higher up on this list.<\/p>\n \n\tBest line:<\/strong> \u201cSpinning on that dizzy edge\/Kissed her face and kissed her head.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\t\u201cHere\u2019s the part where the girl gets pissed,\u201d indeed. Olivia goes off on a hilarious rant against a suspected rival, the only time on Pretty Sad <\/em>she shows her OliviAggro fangs, and it\u2019s the closest she comes to a pop-punk snarler, despite the excellent synth-pop buzz. \u201cMy Way\u201d is deliciously petty, self-mocking, irresponsible, and misogynistic, in the \u201cMisery Business\u201d\/\u201cBetter Than Revenge\u201d tradition. But given how much Olivia worships Blondie, her role model sounds like it must be Debbie Harry\u2019s sneer in \u201cRip Her To Shreds.\u201d <\/a>Fun fact: the most famous cover version of Frank Sinatra\u2019s \u201cMy Way\u201d is the punk makeover <\/a>from the Sex Pistols\u2019 Sid Vicious. In the biopic Pistol<\/em>, it\u2019s sung by the actor playing Sid: Louis Partridge. <\/p>\n \n\tBest line: <\/strong>\u201cMaybe I\u2019m a petty bitch, but you made me resort to this! That\u2019s it! I win!\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tOlivia sings about the kind of compare-and-despair self-loathing that <\/strong>results from excessive phone addiction. She sings about it with all her typical sympathy and wit, especially when she\u2019s scrolling through \u201ccool vintage clothes and vacation photos.\u201d Plus one of her first killer bridges. The studio version is stiff, but \u201cJealousy, Jealousy\u201d really took off as one of her live hell-raisers, with a punked-out Clash-style attack, as she chants, \u201cCo-comparison is killing me slowly.\u201d<\/p>\n \n\tBest line: <\/strong>\u201cA pretty face, a pretty boyfriend too\/I wanna be you so bad and I don\u2019t even know you.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tA torchy change-of-pace piano weeper in cocktail mode, mourning the burnout of a relationship, including a failed getaway to Big Sur. Who among us HASN\u2019T broken down in a crying fit on the curb at LAX?\u00a0<\/p>\n \n\tBest line: <\/strong>\u201cMaybe I\u2019m a stubborn overthinker, but I\u2019ve been thinking over this a lot.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tA moving confession about growing up, maybe even getting famous, from the POV of a hyper-responsible only child and Disney starlet. She got what she wanted, but she doesn\u2019t like who she\u2019s turning into, always pretending she\u2019s older than she is. \u201cGetting drunk at a club with my fair-weather friends,\u201d she sighs. \u201cPush away all the people who know me the best\/But it\u2019s me who\u2019s been making the bed.\u201d\u00a0<\/p>\n \n\tBest line:<\/strong> \u201cI tell someone I love them, just as a distraction\/And they tell me that they love me like I\u2019m some tourist attraction.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tA skeletal demo of a song written after her third album was turned in, released as vinyl-collector bait on the flip side of \u201cThe Cure,\u201d but a very different story about a generic cad. The guy in \u201cThe Cure\u201d tries hard to suck out her toxins, but this guy isn\u2019t trying at all, leaving her to wonder, \u201cNaked in your bed\/Baby, where have you been?\u201d\u00a0<\/p>\n \n\tBest line:<\/strong> \u201cWe both do our best\/It\u2019s a shame that my best is much more.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tShe talks tough to an ex \u2014 but only after their break-up, as she rehashes their old arguments in front of her bedroom mirror. \u201cI was just driving to the studio,\u201d Olivia once said. \u201cAnd I was listening to the Smiths and there\u2019s this lyric [in \u2018I Know It\u2019s Over\u2019] where he says, \u2018It takes courage to be kind.\u2019 I was really upset at the time and I was like, \u2018What if I don\u2019t what to have courage and what if I don\u2019t want to be kind?\u2019\u201d She wrote the lyrics at the next stoplight: \u201cIt takes strength to forgive, but I don\u2019t feel strong.\u201d<\/p>\n \n\tBest line: <\/strong>\u201cHurt people hurt people\/We both drew blood, but man, those cuts were never equal.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tHer great soundtrack theme for The Hunger Games: The Ballad of Songbirds & Snakes<\/em>. It fits the pastoral acoustic folk-horror mode of the franchise \u2014 definitely cut from the same cloth as Taylor Swift\u2019s \u201cSafe and Sound\u201d with the Civil Wars. She sings from the perspective of the heroine Lucy Gray, but she puts her own stamp on it. It\u2019s yet another Olivia song about an older man who planned on picking her up and tossing her away, only to find that she still haunts him long after she escapes.<\/p>\n \n\tBest line: \u201cI bet you figured I\u2019d pass like winter\/Be something easy to forget.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tA powerfully candid tale of negative body image and torturously low self-esteem. It\u2019s almost a foretaste of \u201cThe Cure,\u201d dissecting the destructive thoughts that can prey on an insecure young mind, as she laments, \u201cI bought all the clothes that they told me to buy\/I chased some ideal my whole fucking life.\u201d The heavily flanged guitar is very 1985, a clever sign of producer Dan Nigro\u2019s ever-fruitful Eighties inspiration.<\/p>\n \n\tBest line: <\/strong>\u201cIt\u2019s in my phone, it\u2019s in my head, it\u2019s in the boys I bring to bed.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tShe can lie to everybody else about her feelings \u2014 even the boy in her arms, who she doesn\u2019t really love. But this girl can\u2019t fool her guitar, because it knows all her secrets and gives her the truth. (\u201cYou can tell your guitar things that you can\u2019t tell people,\u201d as Paul McCartney once told Rolling Stone<\/em>. \u201cAnd it will answer you with things people can\u2019t tell you.\u201d) It\u2019s a muted acoustic ballad with some Ladies of the Canyon<\/em> swoops in her vocal.\u00a0<\/p>\n \n\tBest line: <\/strong>\u201cI\u2019m so scared of my guitar\/Because it cuts right to the heart\/It knows me too well, so I got no excuse\/I can\u2019t lie to it the same way that I lie to you.\u201d<\/p>\n<\/div>\n<\/article>\n<\/li>\n \t<\/p>\n \n\tThe massive finale of Guts, <\/em>a piano confession building to the climactic lighters-up chorus. Olivia blows out the candles as she turns 20, singing, \u201cI\u2019m sorry that I couldn\u2019t always be your teenage dream.\u201d (Three years after she sang \u201cI\u2019m so sick of 17\/Where\u2019s my fucking teenage dream?\u201d) <\/strong>But she\u2019s got tough questions for the future, asking, \u201cWhen am I gonna stop being wise beyond my years? And just start being wise? When am I gonna stop being a pretty young thing to guys?\u201d\u00a0<\/p>\n\u20181 Step Forward, 3 Steps Back\u2019<\/h2>\n
\u2018Friday I\u2019m In Love\u2019 (with Robert Smith)<\/h2>\n
\u2018Expectations\u2019<\/h2>\n
\u2018River\u2019<\/h2>\n
\u2018The Book of Love\u2019<\/h2>\n
\u2018Say It Ain\u2019t So\u2019 (with Weezer)<\/h2>\n
\u2018Buddy Holly\u2019 (with Weezer)<\/h2>\n
\u2018All I Want\u2019<\/h2>\n
\u2018Stick Season\u2019<\/h2>\n
\u2018Cigarette Smoke\u2019<\/h2>\n
\u2018Burning Down the House\u2019 (with David Byrne)<\/h2>\n
\u2018Hope Ur Ok\u2019<\/h2>\n
\u2018Traitor\u2019<\/h2>\n
\t\t\t\t\t<\/figure>\n\u2018Just Like Heaven\u2019 (with Robert Smith)<\/h2>\n
\u2018My Way\u2019<\/h2>\n
\u2018Jealousy Jealousy\u2019<\/h2>\n
\u2018Less\u2019<\/h2>\n
\u2018Making the Bed\u2019<\/h2>\n
\u2018Never Do\u2019<\/h2>\n
\u2018The Grudge\u2019<\/h2>\n
\u2018Can\u2019t Catch Me Now\u2019<\/h2>\n
\u2018Pretty Isn\u2019t Pretty\u2019<\/h2>\n
\u2018Scared of My Guitar\u2019<\/h2>\n
\u2018Teenage Dream\u2019<\/h2>\n