Role Model Serenades Al Roker as ‘Sally’ on TODAY Show 2025

A Morning of Music and Laughter

There’s something uniquely magical about the TODAY Show’s Citi Concert Series—a blend of live music, celebrity charm, and spontaneous moments that captivate audiences worldwide. On August 29, 2025, that magic reached new heights when Role Model, the rising indie-pop sensation, turned the iconic Rockefeller Plaza into his personal stage and serenaded none other than Al Roker as his “Sally”. This unforgettable moment was not just a highlight of the summer concert series but a testament to the power of music to create joy and connection.

For those unfamiliar with Role Model (real name Tucker Pillsbury), this performance was a perfect introduction to his charismatic artistry and his ability to transform a simple song into an interactive experience. But what made this moment so special? Let’s dive into the story behind the music, the tradition of “Sally,” and why Al Roker’s participation made headlines.

Who Is Role Model? The Singer Behind the Sensation

Before we unravel the magic of the “Sally” moment, it’s essential to understand the artist behind it. Role Model is a 28-year-old singer from Maine whose rise to fame has been nothing short of meteoric. With his laid-back vibe, introspective lyrics, and knack for blending pop with indie sensibilities, he has quickly carved out a unique space in the music industry.

His album, “Kansas Anymore,” released in February 2025, received critical acclaim and solidified his status as a force to be reckoned with. The deluxe version of the album further expanded his reach, and his “No Place Like Tour” sold out venues across the country earlier in the year. But beyond the music, Role Model is known for his humility and dedication to his craft. In an interview with TODAY.com, he shared:

“I try not to think about [fame] too much. I stick to my little daily routine. But it is very cool that people are coming to shows and enjoying the album, and that’s all you can ask for”.

This down-to-earth attitude shines through in his performances, making him relatable to fans and newcomers alike.

The Tradition of “Sally, When the Wine Runs Out”

At the heart of Role Model’s TODAY Show performance was his hit song, “Sally, When the Wine Runs Out.” This track has become a staple at his concerts, not just for its catchy melody but for the tradition that accompanies it. During live performances, Role Model invites a fan (or sometimes a celebrity) on stage and dubs them “Sally” to dance along with him.

The song itself is a nostalgic yet upbeat reflection on fleeting moments and the warmth of human connection. By bringing a “Sally” on stage, Role Model transforms the song into a shared experience, blurring the lines between performer and audience. Past “Sallys” have included Kate Hudson, Natalie Portman, Reneé Rapp, and social media star Jake Shane. This tradition has become a beloved part of his brand, symbolizing inclusivity and spontaneity.

Al Roker as “Sally”: The Moment That Stole the Show

When Role Model took the stage on August 29, 2025, as part of the Citi Concert Series, the atmosphere was electric. The series, which celebrated its 30th anniversary in 2025, has featured icons like Kelly Clarkson, Blake Shelton, and the Jonas Brothers. But Role Model’s performance stood out for its sheer unpredictability.

As he launched into “Sally, When the Wine Runs Out,” he asked the crowd, “Where’s my Sally tonight?” To everyone’s delight, Al Roker emerged, sporting a cowboy hat and holding a wine glass, ready to play the part. The TODAY weatherman, known for his infectious energy, danced and sang along with Role Model, embodying the spirit of “Sally” with every step.

The moment was both hilarious and heartwarming—a perfect example of how the TODAY Show blends music with moments of genuine human connection. As the Role Model later exclaimed, “Sally, everybody!” The crowd erupted in cheers, cementing this as one of the most memorable moments in the concert series’ history.

The Significance of the Citi Concert Series

Role Model’s performance was part of a larger celebration—the 30th anniversary of the TODAY Summer Concert Series. Sponsored by Citi for the tenth consecutive year, the series has become a staple of American pop culture, bringing fans closer to their favorite artists in an intimate setting.

The 2025 lineup included heavyweights like Ciara, FINNEAS, and Zac Brown Band, but Role Model’s inclusion signaled the show’s commitment to showcasing rising talent. For artists like him, the platform offers unparalleled exposure and an opportunity to connect with a diverse audience.

🎤 Table: Highlights of the 2025 Citi Concert Series

Why This Moment Resonated

Al Roker’s turn as “Sally” resonated with audiences for several reasons:
1. Authenticity: In an era of highly curated performances, this moment felt refreshingly genuine. Al Roker, a beloved public figure, showed his fun-loving side without pretense.

2. The Power of Tradition: Role Model’s “Sally” tradition is a brilliant example of how artists can create rituals that deepen fan engagement. By including Al Roker, he expanded this tradition to a broader audience.

3. Cross-Generational Appeal: The collaboration between a young indie artist and a veteran TV personality bridged generational gaps, appealing to both Role Model’s fans and longtime TODAY Show viewers.

The Rising Star of Role Model

Role Model’s appearance on the TODAY Show is just one chapter in his rapidly evolving career. In addition to his music, he has ventured into acting, with an upcoming role in Lena Dunham’s comedy feature “Good Sex”. This diversification highlights his versatility and suggests that his influence will extend beyond music.

His ability to balance humility with ambition makes him a true role model singer in every sense of the phrase. As he continues to grow his audience, moments like the “Sally” tradition will undoubtedly remain a cornerstone of his artistic identity.

Conclusion: The Magic of Live Music

Role Model’s serenade to Al Roker as “Sally” was more than just a viral moment—it was a celebration of music’s ability to bring people together. Whether you’re a longtime fan of Role Model or just discovering his music, this performance encapsulates everything that makes live music special: spontaneity, joy, and shared experiences.

As the TODAY Show’s concert series continues to evolve, we can only hope for more moments like this—where music and humanity intersect in the most delightful ways.

Did you catch the Role Model’s performance on the TODAY Show? Share your thoughts in the comments below, and don’t forget to check out his album “Kansas Anymore” for more unforgettable tunes! For updates on future Citi Concert Series events, visit TODAY.com/concerts

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