Role Model—born Tucker Pillsbury—made a memorable musical guest debut on Saturday Night Live on October 11, 2025, delivering a pair of performances drawn from the deluxe edition of his sophomore record, Kansas Anymore.

Introduced by host and former SNL cast member Amy Poehler, the 28-year-old opened with his breakthrough single “Sally, When the Wine Runs Out,” a track that recently climbed to No. 1 on Billboard’s Adult Alternative Airplay chart.

The number unfolded against a moody, rustic set—hay bales, a wooden ladder and dim lighting—while Role Model wore a brown shirt paired with glittery blue jeans. Historically, the song’s live renditions have included surprise stand-ins for the role of “Sally,” with notable guests and fans previously joining him onstage.

Midway through the performance he called, “Where’s my Sally tonight?” prompting a surprise appearance by Charli XCX. Dressed in a black skirt, dark sunglasses and a “Max’s Kansas City” T-shirt, Charli sashayed in, shared a playful dance with Role Model, slipped her shades onto him, blew a kiss and exited as abruptly as she’d arrived.

Viewers quickly took note of Charli’s T-shirt, sparking online speculation that it might be a pointed reference amid ongoing chatter about her relationship with Taylor Swift. Those conversations intensified after Swift released “Actually Romantic” from her latest album, The Life of a Showgirl, which some listeners read as an answer to Charli’s “Everything Is Romantic” from Brat.

For his second slot, Role Model stripped things back with a tender acoustic rendition of “Some Protector,” performing solo with a guitar and delivering an intimate, emotive turn.

Watch both SNL performances below.

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