I Saw Role Model’s ‘Sally’ Destroy at Lollapalooza, and Now I Get Him

I Saw Role Model’s ‘Sally’ Destroy at Lollapalooza, and Now I Get Him


This is an edition of the newsletter Pulling Weeds With Chris Black, in which the columnist weighs in on hot topics in culture. Sign up here to get it in your inbox every Thursday.


A few months ago, my friend Shaad D’Souza, an excellent music writer from Australia who lives in London, sent me a link to a song by an artist who goes by Role Model. Upon first glance, the whole thing screamed “TikTok sensation”—maybe it was the haircut, the clothes, or his past relationship with the content creator and coffee impresario Emma Chamberlin. Role Model’s government name is Tucker Harrington Pillsbury, which is so extreme and insane I couldn’t help but put it on. I listened to 30 seconds of his hit “Sally, When the Wine Runs Out” and went on with my day.

After that initial exploration, I started being followed by Role Model videos on Instagram. Every night, he brings out a different “Sally” to dance with him on stage. The list is long and wide-ranging. Reneé Rapp, Bowen Yang, Natalie Portman, Kate Hudson, and Troye Sivan have all graced the stage, with varying levels of success. He brought his mother out once. At Lollapalooza, I went with The Dare to witness his “Sally” moment, and I was blown away by the size of Role Model’s crowd. People were losing their fucking minds for this guy. I decided I would give the album another listen.

I’ve never noticed this before, but today’s pop superstars don’t have male equivalents. Sabrina Carpenter, Chappell Roan, Gracie Abrams, and Olivia Rodrigo all belong to a club of powerful women who have massive pop hits and can sell tickets. What does the male version of this look like? The era of hip-hop superstars is over for now. And although country has gained real pop market share in the last decade, Morgan Wallen or Zach Bryan still don’t quite fit that bill. Unfortunately (if you ask me) the male versions might be people like Sombr and the enemy of Pulling Weeds, Benson Boone—artists who feel like industry plants constructed in a lab in Culver City according to data-driven marketing insights.

Role Model is firmly in this category, too. But overall, his second album Kansas Anymore feels like big-swing pop music made by guys who can play real instruments, even if some of his less successful songs lean into dreaded “stomp clap” territory. Upon further listening, “Sally, When The Wine Runs Out” has bits of Simon & Garfunkel, The 1975, Fleetwood Mac, Carly Simon, and The Format. The melody and chord progression instantly feel both nostalgic and familiar, the perfect blend for success.

Pillsbury is a white guy from Maine who started as a rapper, then smartly pivoted. He’s named Mac Miller as a key influence, but whenever he comes close to rapping, it reminds me not of Miller, but of Stephen Jenkins from Third Eye Blind, another former rapper who mercifully picked up a guitar and produced one of the most classic late-’90s alternative radio albums of all time. Pillsbury also reminds me of forgotten major label bands like Augustana, but his look (and ex-girlfriend) helps him appeal to the same people who are spending their mortgage payment on Taylor Swift tickets.





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Kevin Harson

I am an editor for Entrepreneur South Africa, focusing on business and entrepreneurship. I love uncovering emerging trends and crafting stories that inspire and inform readers about innovative ventures and industry insights.

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