Reggie got kicked out before he sang a single note. A transit worker at the first stop told him singing was against the rules, prompting Reggie to call it ‘the town from Footloose, where they can’t dance.’ What followed was a day-long wander through New York City with a guitar and one simple ask: will you sing a song with me? Nobody could have predicted where it ended.
The worship leader balancing a guitar and a workout
At the South Street Seaport, Reggie spotted a man named Raheem mid-boxing practice and made his pitch anyway. Raheem pushed back immediately. ‘You said sing a song, not rap a song,’ he told Reggie, drawing a hard line between Drake and Busta Rhymes on one hand and actual melody on the other. It turned out Raheem is a worship leader at his church, and when Reggie offered up ‘Never Would Have Made It,’ Raheem did not hesitate. The two of them sang the full run of the song in the open air, Raheem still holding his boxing equipment. When Reggie asked how he felt afterward, Raheem delivered the most honest post-performance review possible: ‘I feel tired.’ Then, after a beat: ‘I’m very happy that I sang.’
A Pillsbury house, a turned-inside-out shirt, and an unexpected duet
Later that same afternoon, a security perimeter appeared near the Seaport. A film crew had built a full Pillsbury house activation on-site, and the man at the center of it was Jimmy Fallon. Reggie was turned away at the perimeter, then turned away again. His producer Lauren hatched a workaround: send Reggie into the Pillsbury experience as an ordinary participant, guitar in hand. They made him turn his shirt inside out to hide any branding before he joined the line.
Once inside the dome, Reggie played a quick jingle he had written on the spot. Fallon heard it, walked over, and told him to keep going. Reggie obliged with an improvised tribute: ‘Hey, Jimmy, you’re the best host in the world, there’s no one better than you, you’re the number-one host.’ Fallon’s response, after a moment of apparent delight: ‘You play that all the time?’ Reggie answered, completely straight-faced: ‘Every single day.’
Fallon then asked if he could play the guitar himself. Reggie handed it over. Fallon strummed some chords and the two traded lines on an improvised song, ‘We’re gonna rock and roll with Jimmy Fallon,’ right there inside the activation dome in front of a small crowd. When a handler came to move Fallon along, he handed the guitar back and told Reggie: ‘I didn’t know you play rock and roll. I’m gonna come back.’
Raheem’s boxing gloves, still in hand
Raheem never put his equipment down during the song. He stood at the Seaport with his gear in both hands and sang a full gospel chorus with a stranger, then walked back to his workout.
Reggie left the Pillsbury dome the same way he had arrived: on foot, guitar in hand, shirt still inside out, somewhere in lower Manhattan.
