John Anderson’s Biggest Billboard Hits: ‘Swingin’,’ ‘Straight Tequila Night’ & More

John Anderson, the country singer-songwriter whose unmistakable drawl and traditional sound made him one of country music’s most distinctive voices, died Wednesday (Oct. 21) at age 71.

Anderson placed 58 songs on Billboard’s Hot Country Songs chart from 1977 through 2006, including five No. 1s and 20 top 10s. His greatest commercial successes arrived in two distinct waves: an early-1980s breakthrough and a resurgence a decade later.

His chart history began in December 1977 with “I’ve Got a Feelin’ (Somebody’s Been Stealin’),” which peaked at No. 62. After several more modest entries, “1959” became his first top 10 in February 1981, reaching No. 7. He followed with “I’m Just an Old Chunk of Coal,” a Billy Joe Shaver composition that reached No. 4 that year, marking his first top five hit.

Anderson’s first No. 1 led that December: “Wild and Blue,” which launched an especially successful chart run. “Swingin’,” which he co-wrote with Lionel Delmore, followed in March 1983. The playful hit also crossed over to the Billboard Hot 100, where it reached No. 43, and earned the Country Music Association’s single of the year award. “Black Sheep” became Anderson’s third Hot Country Songs No. 1 that December.

Anderson’s chart success continued through the 1980s, though his next No. 1 would come nearly nine years after “Black Sheep.” In March 1992, “Straight Tequila Night” returned him to the top of Hot Country Songs, sparking another high-profile chapter in his career.

The comeback proved more than a one-song revival. “When It Comes to You,” written by Mark Knopfler, reached No. 3 that July, followed by Anderson’s self-written “Seminole Wind,” which peaked at No. 2 that October and became one of his signatures. “Money in the Bank” cashed in as his fifth No. 1 in July 1993.

Anderson maintained a strong country radio presence through the mid-1990s, adding top five hits in “I’ve Got It Made,” “I Wish I Could Have Been There” and “Bend It Until It Breaks.” His final Hot Country Songs entry came in October 2006, “If Her Lovin’ Don’t Kill Me.”

Anderson entered the Nashville Songwriters Hall of Fame in 2014 and the Country Music Hall of Fame in 2024. On Sunday (Oct. 18), just three days before his death, he attended the latter organization’s induction ceremony in Nashville, where Tim McGraw, Paul Overstreet and the Stanley Brothers were honored.

Nearly three decades of chart prominence tell the story of an artist who stayed true to his musical roots while finding new audiences along the way. Billboard counts down Anderson’s 25 biggest Hot Country Songs hits below.

John Anderson’s Biggest Billboard Hits chart is based on performance on Billboard’s weekly Hot Country Songs chart through the Oct. 24, 2026, ranking. Songs are ranked based on an inverse point system, with weeks at No. 1 earning the greatest value and weeks at lower ranks earning less. Due to changes in chart methodology over the years, eras are weighted to account for different chart turnover rates over various periods.

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