Wayne Brady Recalls His Financial Journey And Now Paying It Forward—”All I Needed Was $56 And Didn’t Have It”

BEVERLY HILLS, CALIFORNIA – MARCH 14: Wayne Brady attends the 35th GLAAD Media Awards – Los Angeles at The Beverly Hilton on March 14, 2024 in Beverly Hills, California. (Photo by Matt Winkelmeyer/Getty Images for GLAAD)

For as long as many of us can remember, Wayne Brady has been a friendly face on our screens. The singer, actor and comedian’s career spans decades, and he’s enjoyed crossover success in television and broadway.

But it wasn’t always that way for him. Early on, he struggled to secure steady employment in entertainment, and it was the kindness of his network that helped provide the resources he needed to float him while he was on the climb. Now, he’s partnered banking app Chime to lead conversations portrayed in video series with everyday people about how they perceive financial generosity even while living paycheck to paycheck. While they shared their stories, he dug deep about his own money moments that changed his life forever.

“I’ve been there,” Brady tells ESSENCE, explaining that he understands the plight of deep financial constraints while also having ambitious goals. “I know the feeling of how a specific amount of money could change your life. And I don’t know if people that now enjoy remember the other side of it. But I do.”

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He goes on to tell ESSENCE, “I remember the day when 56 dollars would change my life. That’s the amount that I needed to pay a parking ticket to avoid getting my car booted. That would have stopped my car. And I needed my car to get to my job to pay the ticket. I remember that day and I remember a lot of days like that.”

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These early experiences led him to say “yes” to a partnership with Chime when asked to host its “Pay Progress Forward,” a unique video experiment that explores the relationship between financial well-being and the spirit of generosity.

The initiative stemmed from data from the app that found 83% of Americans believe they’d be even more generous if they were more financially secure.

Brady says he can personally attest to this. His late grandmother Valerie, a strong maternal figure in his life, was the pillar of generosity despite coming from normal means. A hard-working Caribbean woman that once cleaned rooms at Walt Disney World, was the lifeblood of her family; Brady says charitable ideals were instilled in him from watching her his entire life.

Early in his career, Brady said he was offered a life-changing opportunity as a club singer, but he needed to come equipped with his own tuxedo. He didn’t have one, and also had no means to get it.

“I was dead broke at that particular point and I’ve been working but the jobs were small jobs and I got an offer that potentially could put a lot of money in my pocket. But I didn’t have any money,” Brady tells ESSENCE. “My car had been repossessed, I was three months behind on rent mama and we were gonna have to move out of our apartment in North Hollywood. I told my grandmother I needed to go do the job so I can put everything back on track. I need $200. And it was silent for a second and she said ‘Okay when?’ The money was sent almost immediately. I later found out that that was her last $200.”

He went on to get the job and work to pay her back for the huge sacrifice up until the point of her transition. To this day, Brady shares he didn’t know where his life would be without the immense sacrifice his grandmother made.

“That woman had nothing in the bank, but she banked on me.”

While he acknowledges how monumental the act of kindness was, he also warned against big-hearted people financially overextending themselves financially in the name of love.

“There are so many ways to show generosity besides giving money you don’t have,” he tells ESSENCE. “You need to put your mask on first. You need to make sure that you are in a place to be generous with people. Buying a meal or buying clothing for someone is something you can help a person with instead of offering cold hard cash. I believe that generosity can come in all of those forms. So, take care of yourself to make sure that you are a bedrock. So that you can help those that need to rely on you.

The full “Pay Progress Forward” video experiment can be seen here.

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