Stephen Thomas Erlewine's AllMusic biography files Cole Swindell among the linchpins of the breezy country-pop that got tagged bro-country, a sound that blended rock and hip-hop into country, which goes a long way toward explaining why he fits a weekend that also books Nelly and Gucci Mane. He was writing it before he was singing it. Swindell, from Bronwood, Georgia, met Luke Bryan, a fellow Sigma Chi, at Georgia Southern, and after leaving school in 2007 he sold Bryan's merch and wrote songs in his spare time. Bryan cut several, "Roller Coaster" among them. Warner signed Swindell in 2013 on the strength of "Chillin' It," a single he'd first put out himself, and it went to No. 1 on Billboard's country chart.
His label now counts 13 No. 1 singles as an artist, the latest being "Forever to Me" from 2025's Spanish Moss. Three have gone triple Platinum: "Chillin' It," "You Should Be Here" and "She Had Me at Heads Carolina," the Jo Dee Messina remake that won him ACM Single and Song of the Year.
His father died in 2013, and "You Should Be Here" grew out of that. The album named after it turned ten in 2026 and got an anniversary vinyl edition. In June he followed it with "Girl Dad," a song written with Michael Tyler and Ben Stennis about having a daughter his dad never got to meet. His team says it was the most-added song at country radio the week it went out.