Ray Singleton’s Message of Life, Love & Hope

When our publishers were blessed to hear singer, songwriter, and entrepreneur Ray Singleton speak at the ‘I Choose Joy’ Cancer Survivors Brunch in Winston-Salem, there was no question they wanted to share Ray’s inspired message with our readers!

Born and raised in Charleston, SC, Ray graduated from Winthrop University, and later received his M.Ed in counseling from there as well. Loving the area, he decided to make Charlotte his home, and soon met his wife, Roslyn. If the names are familiar, a video of him serenading his beautiful wife before her second brain tumor surgery went viral in 2020, resulting in a heartwarming appearance for the two on the Ellen DeGeneres show in both 2020 and 2022. Roslyn had been first diagnosed with a brain tumor in 2013, but had been clear for six years, until a second tumor emerged.

No stranger to live entertainment, Ray also appeared on America’s Got Talent in 2021 — again serenading his wife and her incredible strength through difficult times. He says his songs for her were initially intended simply to make her smile.


When Ray lost his lovely Roslyn in November of 2022, he vowed to continue her legacy by devoting his own life to spreading a message of positivity around the world. She still inspires him every day. “I feel her all around me! She’s everywhere,” he says. “Roz was my biggest supporter in anything I did. She would come to my shows, listen to me practice the same song all day every day, and tell me how good I sounded.”

His love for her keeps Ray inspired to continue singing, performing, and reaching out to others through the magic of music. “I feel connected to her when I’m singing. I believe she can still hear me singing to her, all the way up in heaven!”

Though he’s been singing his entire life, Ray says he’s a “newbie” in the public speaking arena, and is still discovering how he wants his speeches to flow. “I gained notoriety by singing, so I understand that’s a powerful tool when looking to bring out the emotions in an audience. I want people to really feel after they hear me speak or sing!” he explains.

Listen to his message, even briefly, and you’ll see Ray is a firm believer that ‘things don’t happen to you, they happen for you,’ and that positivity is a daily choice. (Some of us, he points out, have to make that choice several times throughout the day!)

“I’ve found that I simply feel better when I choose optimism,” says Ray. “When I choose to see the silver lining in a situation, I can still find positivity because of my attitude of gratitude. I’m grateful for my life, my family, the time I got to spend with my beautiful wife before God took her back to heaven, and the wonderful experiences I’ve had so far in this short life. I feel more productive when I’m positive, and I feel like I attract more positivity by being positive!”

His message may also remind us that yes, life is tough! It can be unfair, unfavorable, and unforgiving. “But positivity is a personal choice, and I choose it as often as I can!” he adds.


About his music: Ray and his core bandmates have been together since their college days. “We’ve played small open mic events on and around the campus, we’ve played music festivals in Rock Hill and Charlotte, and been regulars at countless pubs and bars around the city as ‘in-house’ entertainment.” 

Their repertoire includes music videos, weddings, birthday parties, any type of gathering that needs awesome music! “Our name is ‘Pull Up & Play’ because that’s what we do! And every single time, IT’S A PARTY!”says Ray.

That’s what Roz would want.

As an entrepreneur, Ray also represents Helping Hand Funds Recovery, LLC, an asset recovery firm that he started a year ago. “We assist individuals and businesses in filing claims that are open with their county after the foreclosure of their property. I not only run this business, I teach others how they can get involved as well. He also plans to hold Master Classes on the topic in the future. (Visit www.helpinghandfunds.com)

Often asked for his best life advice, Ray is all about honesty. “The facts are this: We are all going to die. What we do with that information now is what’s important! Are you more grateful for your family, your loved ones, your friends, and all the opportunities afforded you? Life is absolutely not promised! If you have the chance to wake up, you have the opportunity and responsibility to ENJOY every single second. Choose to live!”

To reach Ray, email info@theraysingleton.com, or visit his website theraysingleton.com (where you can also book him for your next event!) You can also follow him on Instagram @willie_qool.


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