Hudson Westbrook picked up a milestone this week: his single “Painted You Pretty” debuted at No. 93 on the Billboard Hot 100, the 22-year-old’s first-ever entry on the chart.
The song, the second radio single off his debut album Texas Forever, had already spent months climbing Billboard’s Country Airplay and Hot Country Songs charts, along with a run atop the Bubbling Under Hot 100. Its jump onto the main chart caps off a stretch that’s included television performances on Today and The Kelly Clarkson Show.
Westbrook’s rise happened fast. He first broke through in 2024 with the viral hit “Take It Slow” while still enrolled at Texas Tech University studying energy commerce, working at a feed store on the side. He left school in the fall of 2025 to pursue music full time, and has since racked up more than 1.2 billion global streams and a Billboard Country Rookie of the Month nod.
His debut single at country radio, “House Again,” reached No. 1 on the Mediabase country chart in February, making Westbrook the youngest solo male artist ever to top the country airplay chart with a debut single. “House Again did the dang thing,” he wrote on social media after the milestone hit.
That song, inspired by his parents’ divorce, became the flagship of his 2025 debut album. Its success helped fuel a breakout year: Westbrook has spent 2026 alternating headlining shows with opening slots for some of country’s biggest names, including George Strait, Morgan Wallen and Bailey Zimmerman.
Westbrook just released “Made You Look,” the title track off his sophomore album due Nov. 6, and he kicks off his own 24-date headlining “Hits Me Tour” on Sept. 18 with two sold-out shows at Billy Bob’s in Fort Worth, Texas, hometown turf for the singer who was still working at a feed store when his music career first took off.
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