Role Model brought his breakout hit to the biggest stage tonight as the rising artist headlines the 2026 NHL Winter Classic in Miami. The Maine-born singer performs “Sally, When the Wine Runs Out” during first intermission. Fresh dating rumors with Dakota Johnson are heating up the star’s year.
🔥 Quick Facts
- Role Model headlines entertainment at 2026 Winter Classic in Miami on January 2
- The Maine-born artist performs his smash hit “Sally, When the Wine Runs Out” during first intermission
- Florida Panthers vs. New York Rangers on loanDepot park with roof open at 8 p.m. ET
- Dating rumors with actress Dakota Johnson intensified after recent cozy dinner spotted by paparazzi December 29-31
Role Model Takes Stage Tonight at Historic NHL Winter Classic
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The NHL announced in December that rising singer-songwriter Role Model would headline entertainment for the 2026 Winter Classic at loanDepot park in Miami. The 28-year-old artist, whose real name is Tucker Pillsbury, will perform during the first intermission presented by Ticketmaster as the Florida Panthers host the New York Rangers.
The Winter Classic marks only the second outdoor game in Florida history. Multi-platinum artist Luis Fonsi will perform during the game’s opening. The atmosphere promises to be electric with mild Miami weather expected and the iconic roofless venue creating an intimate concert experience for hockey fans worldwide.
Sally, When the Wine Runs Out Becomes Chart-Topping Breakout Hit
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Role Model’s “Sally, When the Wine Runs Out” has become his biggest breakout moment. The track went viral from TikTok videos and was released as an official single on February 14, 2025. The song features Role Model inviting fans onto the stage for an interactive performance moment during the bridge.
The Maine-born artist earned his first-ever Number 1 on the Adult Alternative Airplay chart with “Sally.” He recently performed the track on Saturday Night Live in October, where it resonated with both critics and audiences. Fans have embraced the song’s earthy charm and nostalgic lyrics about love and loss.
| Category | Details |
| Song Title | Sally, When the Wine Runs Out |
| Release Date | February 14, 2025 |
| Album | Kansas Anymore (The Longest Goodbye) |
| Chart Peak | No. 1 Adult Alternative Airplay |
Role Model’s Rising Career From Maine Music Student to NHL Headliner
Tucker Pillsbury was born on May 15, 1997, in Cape Elizabeth, Maine. He initially pursued film studies at Point Park University in Pittsburgh before discovering his musical voice nearly a decade ago. The artist began as a rapper before evolving into the alternative-pop singer fans know today.
His parents, Rusty Pillsbury (real estate appraiser) and Susan Pillsbury (special education teacher), inspired his creative journey in Maine. He earned a recording contract with Interscope Records in 2018 after building an online following. Role Model released his debut album “Rx” and has since become one of music’s most compelling rising voices.
“Both Johnson and Pillsbury are single. The actress’s years-long romance with ex-fiancé Chris Martin ended this past June.”
— Elle Magazine, Celebrity News
Dakota Johnson and Role Model Spark Christmas Romance Whispers as New Year Begins
The entertainment world is buzzing after Dakota Johnson and Role Model were spotted together enjoying a cozy candlelit dinner during the holiday season. The 36-year-old actress and the 28-year-old musician were photographed by paparazzi, igniting speculation about their relationship status.
Both stars are single following significant relationship endings. Johnson split from Coldplay frontman Chris Martin in June 2025 after years of dating. The two were reportedly seen kissing, dancing, and holding onto each other during New Year’s Eve celebrations, according to sources close to the pair. While neither has confirmed the nature of their connection, the chemistry captured by photographers suggests something more than friendship.
Can Role Model’s Winter Classic Performance Launch Him Into Superstardom?
Tonight’s NHL Winter Classic performance represents a defining moment for Role Model’s career. The sold-out venue combined with national television coverage gives him access to millions of viewers beyond his existing fanbase. Performing “Sally, When the Wine Runs Out” at such a prestigious event could cement his status as a major cultural force.
As dating rumors swirl and his music charts continue climbing, Role Model appears poised for an incredible 2026 ahead. Whether performing for hockey crowds or catching attention from Hollywood’s A-list, the Maine native continues proving that authentic songwriting and genuine artistry resonate with audiences everywhere.
Sources
- NHL Official – Winter Classic 2026 entertainment announcements
- Billboard – Chart performance and music industry coverage
- Elle Magazine – Celebrity dating rumors and relationship news
Jessica Morrison is a seasoned entertainment writer with over a decade of experience covering television, film, and pop culture. After earning a degree in journalism from New York University, she worked as a freelance writer for various entertainment magazines before joining red94.net. Her expertise lies in analyzing television series, from groundbreaking dramas to light-hearted comedies, and she often provides in-depth reviews and industry insights. Outside of writing, Jessica is an avid film buff and enjoys discovering new indie movies at local festivals.