Learning to be adaptable is one of the primary keys to weathering whatever life presents us. The more adaptable we are, the more opportunity to succeed in life.
Dennis “Cash” Roberson learned that lesson early in his life and career. When he was about nine or ten years of age, his older brother, Tony, began playing drums in a group called Hot Chocolate, which had been formed by Lou Ragland, a Cleveland legend. Eight years older than Dennis, Tony began playing gigs with Hot Chocolate at venues like the Ohio State Fair, where they opened for Al Green. For Dennis, “That was a big thing for me at the state fair seeing my brother, who was eighteen at the time, on stage with Green. That’s what opened my eyes to life and show business.”
At that time, The Jackson Five appeared on The Ed Sullivan Show, a variety show featuring a wide range of performers. Dennis’s family was comprised of seven brothers and one sister. So, Tony “… grabbed five of us brothers and he began teaching us to sing. My twin brother, Danny, was Marlon, and I was Michael. That’s what really propelled us to analyze the Jackson Five and what they were doing. And that’s what really started our careers.”
Along with that, Dennis and kids from his neighborhood got together to form a group emulating the Temptations. By the time they got to junior high, they were playing instruments. They entered the school talent show, and people loved them. The following year, Dennis and Danny decided it would be best to be singers and started a group with four members, calling themselves Four of a Kind.
Then, when Dennis was in ninth grade, the group Erroll Gaye and the Imaginations performed at his school. Their manager, Winston Gragg, had heard about Four of a Kind from the talent shows they’d been doing. Dennis and his twin brother were asked to join Erroll’s group. With Dennis sounding like Michael Jackson, just like Erroll, it caused tension, and he quit the group.
Dennis discovered Jimmy Fleming, who was 13 years old that summer and visiting a girl across the street from his house. He told Danny, “Hey, that kid over there favors us.” They approached Jimmy, asking him to join their group. They taught him to sing and dance and recorded their first single titled “I Love You Still” in Los Angeles, CA. It was there that they changed their name to CA$H because there was an established gospel group with the name Imaginations.
With all the changes, people coming and going in the groups, adaptability became the fulcrum by which Dennis, his brother, and other members were able to not let things upset them or throw them off their game. “That’s how we got along in the business, were able to stay focused. We liked the business because it was just what people did — sing, dance, and keep going.” The group got to travel, meet people, and make people feel good through their music.
Throughout it all, Dennis’s parents were supportive, allowing the boys to do what they wanted musically. Even little brother Jeffrey got in on the act when he stepped in at the age of nine years old to play drums at a gig with Al Hudson and One Way in Akron when the group’s drummer showed up drunk. Jeffrey, who started out playing the drums in rehearsals, has stayed in the music business ever since.
CA$H, opened for the Temptations, Blue Magic, Harold Melvin & the Blue Notes, Al Hudson, Curtis Mayfield, the Dells, War, the Moments, Stevie Wonder, The Sylvers, and others. They also had gigs in cities from New York to Los Angeles and for Jesse Jackson’s P.U.S.H. Operation in Chi-town. A fortuitous appearance on Soul Train gained them national attention.
What also caught Dennis’s attention during this time was all the things that went on behind the scenes in the music business. “When I got to the age of 27-28, I started doing more things with people. My little brother was trying to mess around the same as me, working with different people and such. We tried recording things. I learned to produce television because I saw the behind-the-scenes machinations with Soul Train.”
Dennis checked out anything that was entertainment-related, observing, studying, and then taking action. He knew it was all kind of like a shell game. It kept him going, and he was able to take on a lot of new things to keep the music influence going.
Over the years, Dennis has continued to expand his expertise, managing other artists and groups. He has produced the Greatest R&B Legends Music Awards from 2021 to present to honor, acknowledge, and feature the artists who impacted Cleveland’s R&B music scene over the past fifty years.
This year’s 2025 GRBLMA’s honors legends Evelyn Champagne King, Raydio, Enchantment (featuring David Banks), Randy Hall, Cleveland’s legendary group The Hesitations, and more! This year’s event will be held on May 17 at The Civic in Mayfield Heights, Ohio. Dennis Cash, producer of the ceremony, as well as the previous Greatest R&B Legends Music Awards, can be seen on TUBI and Prime.
Meanwhile, Dennis keeps moving forward, being mindful that “If things don’t work out the way you want, remember that it may not be the right time. The music industry isn’t easy. Keep believing in a higher power, and it’ll happen when the time is right. If you do the right thing, it’ll somehow work out down the road. And remember, when the game changes — adapt!”
