Under a canopy of shade at sunset in Plaza de Cesar Chavez, David Brookings sings directly to a lovely lady in the crowd. “I’ve never seen you look as good as you do tonight,” coos Brookings on solo guitar, covering Chris de Burgh’s staple, “Lady in Red.” He’s serenading young Brady, 14 months old and the younger of his two daughters, who is, indeed, outfitted in that very hue.
With a music career that spans close to 30 years and a catalog that now stretches to include seven full-length albums and a best-of compilation, Brookings is clearly serious about his craft. But as moments like this reveal, he still knows how to have fun on stage. “I know so many people that stopped doing music after they had kids, and I can’t fathom that,” says Brookings prior to his performance. In his case, it seems to have added another layer to his passion.
Brookings’ musical beginnings started in his native Richmond, Virginia, with the TV series, The Monkees, though his father’s vinyl collection soon took him even further down the rabbit hole. “I was looking through his records, and I saw the Beatles’ Help! I just thought my hair looked like theirs,” he recalls. “It was the best thing I’d ever heard.” Alongside the Fab Four, he was listening to the Rolling Stones, Chuck Berry, and Herman’s Hermits. He had his first guitar at nine, started writing his own material at 11, and began playing club gigs around Richmond at 15. Brookings adds, “It’s been an obsession ever since.”
After leaving Richmond at 22, Brookings spent time in Memphis, where he logged more than six years as a tour guide at the world-famous Sun Studio, the hallowed ground that established the careers of such legends as Johnny Cash, Roy Orbison, and Elvis Presley. He cut three albums at Sun, all cobbled together with any late-night studio time he could secure. “I did always think and hope I’d give the tour to somebody that could help out,” shares Brookings, whose tours over the years included run-ins with John Mayer, George Carlin, and musical hero Tom Petty. “I never knew it would be Steve Jobs.”
Brookings admits he didn’t even know who the tech icon was until a coworker pointed it out afterward. Jobs’ lawyer tipped him 80 bucks before the private tour and said to not make mention of the man’s condition. Yet, as Brookings slyly adds, “He didn’t say don’t give him a CD.”
Five weeks later, he received an email from the head of iTunes, a message he first thought was spam. He was flown out to Cupertino to tour the Apple campus before he’d ever even touched a Mac but was soon placed on the iTunes team. In October, he’ll celebrate nine years working with iTunes and Apple Music–all thanks to that chance meeting inside Sun. “He changed our lives,” admits Brookings, who likely never would’ve arrived in the Bay Area otherwise. “I got to say thank you to him just about a month before he died. He said, ‘That tour was the most fun I had in Memphis.’ ”
Since arriving in California, Brookings has released two more albums and a compilation of past work, all containing catchy melodies and a tight pop sensibility. David Brookings and the Average Lookings, released in 2016, signals a more open band dynamic, albeit one that doesn’t muddle Brookings’ musical touch. Songs like “I’m in Love with Your Wife”—a playful reframing of Eric Clapton informing George Harrison he’s about to steal his spouse—merge playful lyricism with astute songcraft. “Wife” also shows Brookings injecting his love for history into his writing. Brookings intends to record a followup with the same band this fall in downtown San Jose.
“I’m going to keep writing songs and putting out records until the end,” shares Brookings with a slight southern drawl that still carries the stamp of his hometown. His trove of written material, at this point, surpasses 300 songs, yet he still admits, “I can hear a song and tell where I was. To me, it’s your legacy. When I’m gone, my legacy is going to be my kids and all the songs.”
This article originally appeared in Issue 10.5 “Dine”