Clad in an ever-present white cowboy hat and often armed with his 1968 pink paisley Telecaster, Brad Paisley stands apart as a consummate performer even in a genre rich with them—the flashy guitar is just the beginning. Paisley’s virtuosic chicken pickin’, sense of humor, and myriad non-musical talents have also helped make him a household name. Among those talents are acting and writing, and he even put together Brad Paisley’s Comedy Rodeo in 2017, but his songs remain his true legacy. While many country singers pick a lane, Paisley, born in 1972 in West Virginia, has explored subjects like everlasting love (“Then”), good times (“No I in Beer”), backwoods romps (“Ticks”), and even depression and suicide (“Whiskey Lullaby”). His ability to wear many figurative hats has built him for both prolificacy and longevity, netting 32 Top 10 singles in the two decades after his 1999 debut, Who Needs Pictures. And his knack for cleverly capturing the drama and comedy of the human experiment ensures that even a song like 2019’s “Alive Right Now,” planted firmly in our tech-riddled present, has an element of timelessness. As long as Paisley’s wielding his signature Tele, the laughs—and the tears—will continue.