It’s the morning after a St. Louis jury decided not to indict officer Darren Wilson for the killing of an unarmed black man named Michael Brown and it’s beginning to snow in River Rouge, Mich. Sean Michael Leonard Anderson, better known as Big Sean, is in town with his mom to distribute Thanksgiving turkeys and canned goods to more than 1,000 families in need.

The temperature hovers near freezing, but Sean’s dressed appropriately in a black hoodie beneath a green flannel shirt, a fur-lined parka, black Timbs, and a gray ushanka, the traditional Russian headwear that looks as warm as it does diverting. He makes his way inside River Rouge High School to prepare for the giveaway. Before he does that, though, he agrees to surprise the students attending a holiday assembly in the auditorium.

“No one knows I’m here?” Sean asks.

“No one,” says a school administrator. “It’s a complete surprise.”

On his way to the stage Sean stops and asks a friend if he should remove the hat. He’s unsure of how his hair looks and takes it off to show everyone. Low cut into a tight fade with a swooping part, it looks fine. His mom pleads with him to keep it off: “Sean, when kids are in school, they are told to take their hats off!”

He decides to keep it on. As expected, the students in attendance lose their shit when Sean hits the stage. When the feverish crowd calms down, he talks about the importance of giving back and following dreams before ending with:

“I got love for y’all. I care for y’all.”

After 90 minutes or so handing out groceries, shaking hands, and posing for photos, Sean says his goodbyes. He has more stops to make. While in the area for the holidays, he plans to participate in Detroit’s Thanksgiving Day parade and watch the Lions play the Chicago Bears at Ford Field. But first, he wants to swing by Hot 102.7 FM, the radio station where he used to spit on Friday nights as part of a segment where unsigned hype could duke it out for airtime. The station is housed in an unassuming one-story building in midtown Detroit, a few blocks from the Charles H. Wright Museum of African American History. As he walks in, Sean stops and explains the real reason why this place is so important to him. “This was where I rapped for Kanye,” he says. “Nah, it was right…here,” he corrects himself, taking a few steps farther into the building, trying to remember the exact spot where, in 2005, he convinced Kanye West to listen to a quick 16. ’Ye liked the verse enough to take the young MC’s demo. Two years later, Sean was signed to Kanye’s G.O.O.D. Music imprint. Sean says hello to the staff and does a quick on-air interview.

Next stop is Sean’s high school. Cass Technical is one of the premier high schools in the Detroit area. Diana Ross is an alumnus. Thanks to the help of his grandmother and mother, who stressed the importance of him seeing a different side of society, Sean attended good schools for most of his life. When he was younger he was sent to the Detroit Waldorf School, an institution he credits with sparking his interest in art.

“We had to deliver a morning poem every day and a goodbye poem at the end of the day,” Sean recalls while driving through his city. “It taught me to be open-minded and creative.”

The school also taught him how to deal with a mélange of people. His friends from school were exponentially wealthier than his friends from back home. Sean says being able to feel comfortable around people from various backgrounds has helped facilitate some of the success he’s achieved. “It was good to see both aspects,” he says. “I take pride in being able to hop on a song with Eminem and Kanye, or Jay Z, and then being able to hop on a Fall Out Boy song.”