• Raised on basketball, popstar Andy Grammer will make his dream come true on Friday night: suiting up on an NBA court.
By Jake Fischer
February 17, 2017

Popstar singer-songwriter Andy Grammer is working “furiously” in Los Angeles to finish his third album, currently untitled. The album’s single, Fresh Eyes, has already been a smash hit, but the lifelong basketball fan couldn’t pass up an opportunity to play in Friday night’s NBA Celebrity All-Star game. SI.com caught up with the Knicks fan before his playing debut on an NBA court.

Tucked within the Hudson Valley in Monroe, N.Y., Smith’s Clove Park encompasses 80 acres of green space and activities. Hiking trails wind throughout the property. It features a skate park, a gigantic hill perfect for sledding, and every playing surface for any sport a kid could dream of. The basketball court is where Andy Grammer spent his youth.

Yes, that Andy Grammer, the beaming, hair-perfectly-coiffed singer-songwriter who’s star keeps rising following his breakout “Keep Your Head Up” exploding in 2010. Before Grammer picked up a guitar, the park’s court became the second home for him and his friends. “We would wake up at 9 a.m. and go there, come home at like 10, and you’d realize you just played basketball for 12 hours,” Grammer said. “That was the way of life, man.”

2017 NBA All-Star Weekend: Complete Coverage

Young Grammer was hooked on the New York Knicks, fixated by Larry Johnson’s power, John Starks’ play making and Patrick Ewing’s greatness. He fashioned his game in the mold of a prototypical shooting guard, consistently connecting from distance while parlaying the threat of his shot into dribble-drive opportunities, slicing through defenses to dish off to teammates. “Basketball was every day of my life,” he said. “Wake up with a ball, sometimes I’d sleep with it because someone told me that was better for you.”

By middle school, Grammer struggled sleeping as his eighth grade team’s playbook flipped through his mind. He envisioned Xs and Os, back cuts and pick-and-rolls instead of counting sheep. He dreamed of the NBA. Division-I college basketball was at least plausible. “It’s funny how you have these periods of your life. From the end of sixth grade ‘til college, that was it,” Grammer said. After his sophomore season on junior varsity at Monroe-Woodbury High School, he and three of his Smith’s Clove buddies were promoted to varsity for the playoffs. And that’s unfortunately where Grammer’s hoop dreams began to melt into reality.

He never carved his space in the starting lineup. Before his senior year, three unheralded New York City prospects moved out to the suburbs in hopes of advancing their grassroots profiles and Grammer was limited to sixth man. Being so close to the starting unit, yet still so far, ate at his core. “That was pretty hard for me to handle, like, really hard for me to handle,” Grammer said. His childhood aspirations shattered, Grammer consulted with a therapist. “And then I slowly started to figure out that I sound better on guitar.”

2017 NBA All-Star Preview: Storylines To Watch

Once the “Keep Your Head Up” video, featuring The Office’s Rainn Wilson, went viral—it’s just shy of 15 million views on YouTube—he signed with S-Curve records to create his debut album, Andy Grammer. From there, he toured with Natasha Bedingfield and Colbie Caillat. In 2014, released his second album, Magazines or Novels, including "Honey, I'm Good," which soared to No. 9 on the Billboard Hot 100, and became certified triple-platinum by the RIAA.

Grammer’s rise personally culminated at last year’s NBA Finals, where he sang the national anthem before Game 5 at Oracle Arena. “That was such a crucial game, that was when the Cavs started getting their wind back.” And as Cleveland began rewriting history, Grammer was pestering NBA representatives for an invite to All-Star Friday night. Now, he’ll dress for the West Team in this year’s NBA Celebrity All-Star game, running alongside Mavericks owner Mark Cuban, Baron Davis and Master P.

The three teammates who vaulted to varsity as sophomores alongside Grammer will join him in New Orleans. The crew’s everlasting group-text has been buzzing with scouting reports on his teammates and opponents. “I feel like I’m gonna be coming in around the middle to low-middle of talent,” Grammer predicted. “I gotta believe that Anthony Mackie’s a baller. The little kid from Stranger Things [Caleb McLaughlin] is on the other team and they have really high hopes for him.”

Behind the Body: Nick Cannon talks fitness ahead of NBA Celebrity Game

Grammer has been keeping his game fresh. One of his band manager’s many responsibilities is researching open gyms at each location on tour. Grammer has run several college gyms and local courts the mornings after big shows. “If you can own the court for like an hour, and people can’t beat you, that’s the shit,” Grammer said. “We’ve done that a couple times and people don’t really expect it from me.”

But playing on an NBA court, in a national televised game alongside NBA legends like Davis and Jason Williams will be the ultimate test. “So much of my self-worth is wrapped up in how this goes,” Grammer said. And if he gets crossed over and has a poor shooting performance, there’s always that third album to fall back on. It’s set to release later this year.