Watch All of Role Model’s Best ‘Sally’ Moments So Far — from His Mom to Bowen Yang to Reneé Rapp

Role Model’s Best ‘Sally’ Moments: A Look Back at Special Guests Joining the Singer in Epic Performances

Singer Role Model has been delighting fans with his unique tradition of bringing a special guest on stage to be his “Sally” during the performance of his song “Sally, When the Wine Runs Out.” While sometimes a lucky fan from the audience gets to take on the role, there have been instances where celebrities have shared the stage with Role Model. The 28-year-old artist, who is on PEOPLE’s list of 100 Reasons to Love America this year, has even had his mom, Susan Pillsbury, join him as “Sally” on one memorable occasion. In a recent interview with Rolling Stone, Role Model expressed his hope for a collaboration with Kacey Musgraves in the future, keeping fans eagerly anticipating more exciting moments to come.

At a recent performance at New York City’s Gov Ball Music Festival, Role Model was joined on stage by Conan Gray as his “Sally.” Gray didn’t hold back, giving the singer a big smooch before energetically engaging with the audience and mouthing along to the lyrics. The atmosphere was electric as Gray sported a “Wish I Were Sally” T-shirt and bounced around on stage.

In another unforgettable moment, actress and singer Reneé Rapp shared the spotlight with Role Model during a performance in April. Rapp exuded joy as she interacted with the crowd and the singer, bringing a vibrant energy to the stage. The chemistry between the two performers was palpable, creating a truly memorable performance.

When Role Model made his debut on The Tonight Show, he enlisted the help of SNL star Bowen Yang to join him as “Sally.” Yang brought his A-game, nailing the choreography and adding his own flair to the performance. The duo’s dynamic onstage presence was a highlight of the show, leaving the audience in awe.

During a tour stop in Boston, Role Model brought a familiar face on stage to be his “Sally” – his mom, Susan Pillsbury. Clad in a “New England born and raised” T-shirt, Pillsbury danced around with pride, showcasing the special bond between mother and son. The heartfelt moment resonated with fans and added an extra layer of emotion to the performance.

In a show at the House of Blues Dallas, influencer and podcaster Jake Shane made a surprise appearance as Role Model’s “Sally.” Shane’s infectious energy and the crowd’s enthusiastic response created a memorable interaction between the two entertainers. The genuine connection between Shane and Role Model shone through, leaving a lasting impression on everyone in attendance.

Actor and musician Dylan Minnette brought his star power to an L.A. show earlier this year, strutting around the stage in a tight white shirt. The unexpected collaboration added a fresh dynamic to the performance, showcasing Minnette’s versatility as an artist. The audience was captivated by the onstage chemistry between Role Model and Minnette, making it a standout moment of the show.

As Role Model continues to enchant audiences with his lively performances and special “Sally” moments, fans can look forward to more exciting collaborations and surprises in the future. Whether it’s a fan from the crowd or a celebrity guest, each performance brings a unique energy and connection that keeps fans coming back for more. With a growing list of notable guests joining him on stage, Role Model’s performances are sure to remain a highlight for music lovers everywhere.