All of the Times Drake Has Been Charitable With Fans on His Big as the What? Tour

Before taking the stage for night one of the second leg in Tampa, Drake hooked a stripper up with $10,000 to make sure her first day on the job got off on the right foot. Footage showed the rapper blessing the woman via FaceTime in the backroom of what looks to be an adult entertainment establishment.

“This her first night and he gave her $10,000,” a person said while on FaceTime with Drizzy. “She talking about she fine now. [Drake] gave her $10,000 for her first night here.”

A perseverant fan attended Drake’s Nashville show on Feb. 7 to celebrate finishing chemotherapy and the “Nice for What” rapper took notice of the brave woman’s sign.

“Listen, forget Drake, forget anybody else in this building right now. That’s a true soldier right there,” the rapper said, which drew an ovation from the audience. “I hope my manager doesn’t kill me ’cause I’ve never really done this much, but, listen, I want you to cash this in at the end of the night. We’re gonna give you $100,000. I love you and I wish you the best.”

According to a report from The Tennessean, the fan was identified as Lauren Schwallie and she has been fighting breast cancer since 2022. “One thing led to another and I was at the front of the stage and Drake blew me a kiss and told me that he loved me! That’s all I was focused on … And then just like the money on top of it is just insane,” she told the publication.

Uncle Sam was calling and Drake came to the rescue to bail an OVO fan out of a precarious financial situation.

Drizzy cleared a student’s loan debt with a $20,000 check after reading their sign at the second of back-to-back shows in Nashville Feb. 8.

“I don’t know if I fully agree with you because I feel like student loans gotta get paid,” Drake told the girl from the Bridgestone Arena stage. “But lucky for you, I hope $20,000 will cover it. Cash that in. Pay those student loans off for you.”

Medical bills can be a daunting burden for people without quality health insurance, so a fan shot their shot at seeing if Drake would come through and cover the costs of an upcoming surgery. The half-court heave somehow worked out for them, with the OVO rapper agreeing to bring Canada’s universal healthcare ideology to America.

“You got a sign that says, ‘Please help me with my surgery.’ I don’t know what kinda surgery you need, sir. I really don’t but I’ma let you know from me to you St. Louis love, we gon’ take care whatever the surgery is,” Drake promised. “We gonna help you out because we want you to be at the next show with us. You gotta show us love.”

The fan’s face appeared on the Enterprise Center jumbotron as he emotionally reacted to Drake’s declaration. It’s unclear how much the surgery actually is.

Just about everyone has fond memories of their first car. Maybe it was something that wasn’t the nicest, but it had a certain aura about it that you just refused to let go. One young woman drove 10 hours in her “beater” car — a risky proposition for a drive that distance — to see Drake at his Columbus, Ohio, show.

She also brought multiple signs to communicate with the Toronto rap star. One revealed how Drake’s music helped her get through a time when she was suicidal, and another tugged on his heartstrings: “I drove 10 hours by myself in my beater & still made it.”

After finding out she lived with her family, Drake gifted her $15,000, and another $15,000 to help out her loved ones at home.

“I don’t know what you need in life, but here, take this,” he said. “I’mma give you $15,000 to do what you want to do and I’m gonna give you another $15,000 to your family to make your life sweeter.”

Missing out on a favorite artist’s concert in your hometown can be more heartbreaking than a breakup or seeing your favorite NFL team lose in the playoffs. But Drake did his part to make sure that first situation never arises for one Cleveland superfan.

During a Rocket Mortgage Fieldhouse concert, Drizzy saw the fan’s sign — which listed all the artist’s shows they had been to — on the general admission floor, and promised them free tickets to any show they want in the future for the rest of their life.

“So first and foremost, we’re gonna give you free tickets to any show that you ever want,” Drake pledged.

Seconds after giving away $10,000 to a fan on one side of Kansas City’s T-Mobile Center, Drake walked across the stage and peeped at another looking for a saving grace. This particular fan lost their mother and was hoping the 6 God could pay off his late parent’s mortgage.

The fan sent a letter to Drake on stage showing the outstanding six-figure balance, which made Drizzy pause for a second in shock.

“You said, ‘[Pay] off my mom’s house, rest in peace.’ Your mom passed away? Alright. And you owe …,” Drake said. “Oh, this is the outstanding balance right here. This is a lot of money right here.”

“But you know what, Imma pay off your mama’s house for you,” Drake continued, sending the crowd into a frenzy. “That’s gonna come from me. Rest in peace to your mama.”

“Rich Baby Daddy” will be taking on a whole new meaning for one couple after Drake played the role and wired them $20,000 to alleviate some of the financial stress that comes with having a child.

The soon-to-be parents at the March 3 Kansas City show crafted a sign featuring sonogram photos while channeling the 6 God’s signature gambling tagline: “Expecting our 1st baby in August ANITA MAX WYNN.”

Drake congratulated the couple before fattening their pockets with 20 racks. “Ay, congratulations,” the rapper, who is dad to son Adonis, said. “You about to be a dad? Well, I don’t know what you need for your baby. You probably need like a nice crib, stroller, you know probably take your girl on vacation. I’m gonna give you $20,000.”