‘Listening to mama’ leads to winning singing contest for Winston
You never get too old to listen to your mother’s advice. Just ask Bobby Winston about that.
Winston, a 2004 Russellville High School graduate, is the son of the late Harlan “Peaches” Winston and Linda Winston. He and his brothers, PJ and Siran, grew up having learned to respect and obey their mother and father. It was a lifetime lesson, not one to ‘age out of’ for the Winston brothers. And listening to mama 22 years after high school recently paid off big dividends for Winston when he was named the Tennessee Valley’s winner of the 2026 Star-Spangled Sing-Off, sponsored by Gray Media and WAFF-TV 48 of Huntsville, as part of the company’s ’We The People’ initiative, celebrating America’s 250th birthday on July 4, 2026.
Winston represented the Tennessee Valley in the regional rounds of the contest, with an eventual national winner, who will receive an all-expense paid trip to Nashville to professionally record his or her National Anthem performance, which will be aired on many of Gray Media’s 180 local television stations around the country. The national winner will be announced on Thursday, July 2nd.
It was Winston’s aunt, Karen Phillips, who first learned about the contest, which invited Tennessee Valley residents to submit their best a cappella rendition of our National Anthem. She called her sister Linda, who immediately called her son and ‘gently suggested’ he submit a video entry into the Sing-Off.
“First she said I ought to enter, then she said I needed to enter,” Winston said. “As kids, we learned you’re never too old to get a whipping if you don’t listen to mama, so I did it to make her proud.
“She said ‘get in there and do it, so I said yes ma’am, I’ll get it done. It was the last day to submit an entry, so I had until midnight that Sunday. We went to church, went to dinner and we came home, bellies full. So I just got it done right then,” Winston added.
Singing was also a significant part of the Winston household growing up, Bobby said. With a pastor father who also was blessed with the gift of music, and a mother who was over the youth program at St. James MB Church in Leighton, the brothers were encouraged by their parents to use their musical gifts to encourage and inspire other kids.
“We always had a love for music. And my older brother (PJ) and I performed worship songs mainly, and we actually have written and recorded a number of original worship songs we have always hoped and prayed we could release at some time,” Winston said.
Winston, a physical education teacher and the boys varsity basketball coach at Covenant Christian High School, has never lost his passion for singing, but admits after his father’s passing three years ago, it was pushed to the back burner. He’s hoping his success in the Star-Spangled Sing-Off will create new vocal opportunities.
“It certainly may open some doors, and with my mom encouraging me to do more of it, I’m hoping and praying it will jump start some things for us,” Winston said. “When it’s your time, it’s your time, so hopefully this is my time.”
The contest wasn’t Winston’s first time to publicly sing the Star-Spangled Banner, considered one of the most difficult songs to perform. He sang the National Anthem as a RHS student before a couple varsity basketball games, and at a Northwest Shoals Community College event when he was a student there.
And he and PJ have performed at weddings, festivals and funerals in the Northwest Alabama area. Bobby has opened up for Lenny LeBlanc and for CAIN at the W.C. Handy Festival, to name a few.
And after his success in the Star-Spangled Sing-Off, it will be exciting to see what venues and events Winston will add to his list--all a result of listening to mama.