Kanye West gave a homeless man $100 (£76) and a pair of Yeezy sneakers in his hometown of Chicago on Friday (05Oct18).
During a video taken of the encounter, which was obtained by the MailOnline, the Life of Pablo star was seen taking the details of the homeless man's mother so he could send him a pair of sneakers from his Yeezy collection, which can retail for $200 (£150) to $350 (£266).
Kanye was in Chicago for a trip to the dentist, and approached the man, who was wearing a yellow sweater, after being flagged down.
After walking over to him, the father-of-three handed over his phone so the homeless man could put in his details.
The 41-year-old rapper then instructed one of his security team to give the man some cash.
His generous encounter comes just one week after he invited another homeless man into his recording studio in New York.
The hip-hop star was in the city to perform on Saturday Night Live, and just hours before taking to the stage, he invited Nino Blu into the Electric Lady Studios after seeing him sleeping outside.
Nino told The New York Post that Kanye invited him inside the recording studios for a 40-minute chat over a “strawberry and kiwi smoothie” and some “very exotic tasting soup".
Kanye has been spending more time in the Windy City after he revealed last month (Sep18) he was planning on moving back to his hometown.
"I gotta let y'all know that I'm moving back to Chicago and I'm never leaving again," he said while at an event in Chicago with Chance the Rapper.
According to TMZ, the rapper plans on relocating his business offices to the city, but the West/Kardashian family home will remain in Los Angeles.