Toby Keith, who hit #1 on the country singles chart 20 times with songs that ranged from honky-tonk shuffles to ballads to Southern rock, died Monday in Oklahoma. He was 62.

Keith had been receiving treatment for stomach cancer since 2022.

A writer as well as a performer, Keith arrived on the country music scene in the early 1990s with a style that was big on bravado, boozing and the red, white and blue. He released 21 albums and sold more than 40m albums worldwide.

After working in Oklahoma oil fields after high school, Keith started playing in local bars before heading to Nashville where he busked on street corners. His demo tape led to a deal with Mercury Records. His 1993 self-titled debut went platinum and four Top 5 singles, including “Should’ve Been a Cowboy.” The follow-ups, 1994’s Boomtown and 1996’s Blue Moon (A&M), had similar success, yielding the #1 singles “Who’s That Man?” and “Me Too.”

Keith moved to DreamWorks Records in 1998 where his larger-than-life persona became his calling card as he released five albums in a row that went platinum and between 1999 and 2005 he hit #1 a dozen times with career-defining songs such as “How Do You Like Me Now?,” “Courtesy of the Red, White and Blue (The Angry American),” “Beer for My Horses” with Willie Nelson, and “I love This Bar.”

He founded his own label, Show Dog Nashville, in 2005 and he continued to crank out hits with drinking often being the subject matter; “Red Solo Cup,” for example, was certified triple platinum and was one of his biggest crossover hits. His last country #1 was “Made in America” in 2011.

Keith expanded his operation to included acting in films and commercials and owning restaurants and clothing lines. In 2013, Forbes magazine tagged him as country’s $500m man. He was inducted into the Songwriters Hall of Fame in 2015 and received the National Medal of Arts in 2021.