Where’s My Sally Tonight?

BY Maggie Foster ★ October 24th 2025

Design by: Olivia Rosen

“Where’s my Sally tonight?” is a common question asked by Tucker Pillsbury, better known as Role Model, a rising superstar, at his concerts. It is not just a catchy concert phrase, but has become a signature part of his performances that leads to the unveiling of a special guest or highlighted fan. Who’s Sally? What's Sally? Why does he stop in the middle of a song to call up Sally?

In 2025, Pillsbury released the studio album Kansas Anymore (The Longest Goodbye), which features a song titled “Sally When the Wine Runs Out.” It is an upbeat song about love and the love leaving after the wine runs out. Lyrically, the song captures the fleeting nature of romance; how passion can fade just as quickly as it blooms.

While on his tour, No Place Like Tour, Pillsbury surprised the audience in Dallas on Feb. 27, 2025, with Jake Shane as the first Sally. That night, Pillsbury shocked fans by bringing out the social media star and podcaster, and the choice to bring out Shane fueled the viral trend. Ever since, concert goers would try to predict who the next “Sally” was going to be. 

The concept of Sally grew beyond the song itself. On his No Place Like Tour, Pillsbury turned the idea into an interactive, almost theatrical moment during each show. In the middle of his set, he pauses and calls out, “Where’s my Sally tonight?” The crowd erupts, waiting to see who will take on the role for that city. Sometimes it’s a celebrity guest, sometimes a surprise friend, and other times, a fan chosen from the audience. It’s a unique blend of spontaneity and showmanship, a moment that captures the heart of Role Model’s creative style: personal, charming, and effortlessly cool.

Since then, Pillsbury has kept the tradition alive, inviting an eclectic mix of celebrities to step into the role. The list of past Sallies reads like a who’s who of pop culture: Kate Hudson, Natalie Portman, Bowen Yang, Renee Rapp, and, most recently, Hilary Duff, who joined him onstage to the surprise of fans at the Austin City Limits Festival. Each appearance brings its own energy and uniqueness to the show.

The “Sally” phenomenon even made its way to Syracuse University last year, when Role Model brought the tradition to campus during his Juice Jam performance, giving students their own unforgettable moment to join in on the viral trend.

At its core, the Sally phenomenon reflects something more about Role Model’s artistry. His music often explores human connection, vulnerability, and the tension between love and loneliness. By making Sally a recurring, living part of his concerts, Pillsbury invites fans to participate in that emotional narrative. 

Whether she’s a symbol, a muse, or simply a bit put on by Pillsbury, Sally has become a vital part of Role Model’s world. Sally has become a reminder of how people love live music, and it is magical.

Edited by: Ava Robbins