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How to leave behind a pop legacy, with Sabrina Carpenter and Grace Jones 

A one-two punch at Outside Lands’ biggest stage left city reporter Eddie Kim daydreaming about the blueprint of pop timelessness

Excuse me for the late Sunday morning post — I’m still groggy after taking two hits of pure pop greatness straight to the face last night at Outside Lands.  

Leave it to two unlikely queens of pop, who delivered a one-two punch at the Lands End stage to close out Saturday’s slate. 

For Sabrina Carpenter, the blonde Polly Pocket of TikTok Pop, Outside Lands served as a triumphant coronation — her first time headlining a festival, right on the cusp of her first-ever world tour. And despite my gag about TikTok, Carpenter proved on Saturday why she’s not merely coasting on the viral success of tracks like “Espresso” and “Please Please Please,” even when a lesser artist could. 

That those tracks are two of the biggest, most replayed tunes in the world right now is a testament to a decade of grinding with little recognition. I would know — I’ve been listening to Carpenter for years, wondering when the Disney Channel star (of Girl Meets World fame) would shed the obvious corporate machinations defining her early sound. (I recall the hilariously dated use of a cutesy ukulele in her 2014 debut single, “Can’t Blame a Girl for Trying,” and the weak attempts at big-beat R&B in later years amid the rise of Kehlani and SZA.) 

All that tentative blandness fell away at the drop of her critically acclaimed 2022 record, Emails I Can’t Send. In its place was a gleaming love letter to retro-hued pop, imbued with touches of country, folk and 1970s rock. 

More than anything, the record centers Carpenter’s penchant for flirtatious wit and biting wordplay. Those traits leaped off the page and onto the stage on Saturday night, as Carpenter shimmied her way through an hour of hit after hit. She kicked off with the rollicking but melancholy “Fast Times,” where she bemoans her habit of rushing into infatuation: “No time for rewrites, we couldn't help it. Outlines on bed sides, yeah … give me a second to forget I ever really meant it.”

I was about 50 yards away from the front of the stage, surrounded by fellow superfans who sang every word (no screeching over Carpenter, thankfully, as witnessed at some other shows). We erupted over “Feather,” finding just enough physical space to mime the choreography in the pre-chorus: “I slammed the door. I hit ignore. I’m saying no, no, no, no more,” Carpenter sang, throwing up a kick and dialing an imaginary phone. 

And the energy kept growing, especially when Carpenter brought out country princess Kacey Musgraves in a surprise performance of Nancy Sinatra’s “These Boots Are Made for Walking.” But there were quieter moments to remember, too, like when a fan threw a friendship bracelet onto the catwalk where Carpenter stood.

“No, no — don’t throw things. I’ll kill you,” Carpenter said with a half-joking snarl.  

Then she peered at the object, and grabbed it with a smile after recognizing it.

“I’m glad you threw it,” she said with a grin. 

Her ease with the crowd reminded me of the set just before Carpenter’s on the main Land’s End stage, where 76-year-old icon Grace Jones delivered an utterly timeless show. I stared in awe as she emerged levitating over the stage, seemingly wearing a 40-foot-tall dress. As she sang the opening strains of Iggy Pop’s “Nightclubbing,” I realized it was almost 10 years to the month since I saw her last, at 2014’s FYF Festival in Los Angeles. 

She had blown me away then, too. I had no idea who Jones was, but there she stood, breasts out, covered in wild streaks of body paint, belting like a 22-year-old while her impeccable band ripped funk riffs in the background. 

Her chest wasn’t bare at Outside Lands, but somehow, time has not progressed for Jones in the last decade — she brought the same verve to renditions of “Pull Up to the Bumper” and “My Jamaican Guy” as she had way back then. At one point, she demanded to get off the stage and walk among the audience. Befitting a queen, a smiling security guard let her sit on his broad shoulders, guiding her along the cheering masses as if on parade. 

Taylor Swift may have popularized the idea of an “eras tour” with costume changes, but Jones has been doing that since the 1970s, when she transitioned from being a supermodel (for the likes of Kenzo and Yves Saint Laurent) to a rising pop darling who captured disco, funk and even punk-rock vibes in her tunes. 

As she sang, bantered and sipped red wine from a glass, Jones won over the entire audience, most of which seemed unfamiliar with her oeuvre. For her final songs, she donned a gleaming helmet more befitting a Marvel villain than a pop star, and then busted out her trademark hula-hoop for the hit “Slave to the Rhythm” — a hypnotizing funk romp that highlighted Jones’ booming alto voice, unchanged from her youth. 

I thought of Jones a lot during Carpenter’s set, especially as the latter concluded with an impeccable rendition of “Espresso,” inspiring the crowd to scream along to the chorus: “Say you can’t sleep, baby I know — that’s that me, espresso!” 

How do you leave a pop legacy? Through time, surely, but Jones isn’t magnetic today because she’s been putting out music in the last decade. She hasn’t — her last album arrived in 2008 — but what remains indelible is her ability to read an audience and hold them in the palm of her hand. It is the alchemy of charisma and talent, borne from unlikely origins in fashion. And Jones, in all her impeccable taste and chameleonic spirit, serves as a blueprint for every other ascendant pop star, too.  

Carpenter, as big as she may already be, is only now just realizing her full power. I saw it in her astonished gaze as she peered into the dark, vibrating mass of humans stretched across the Polo Field at Golden Gate Park. In every shake and wink on Saturday, Carpenter embodied the growing confidence of a performer shedding their child-star past — and hitting their prime.

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