At age 90 and with more than seven decades of music under his belt, Texas native Willie Nelson is busier than ever. The 12-time Grammy winner was recently inducted into the Rock n’ Roll Hall of Fame on Nov. 3 and in September, he released Bluegrass, his first full-length album of bluegrass-styled music. The album has earned Nelson a Grammy nomination for best bluegrass album, leading into the 2024 ceremony.

On Dec. 17, CBS will present the music special Willie Nelson’s 90th Birthday Celebration, honoring the music icon with performances and collaborations from Nelson as well as Gary Clark Jr., Snoop Dogg, Miranda Lambert, Norah Jones, George Strait, Chris Stapleton, Keith Richards and Nelson’s sons Lukas Nelson and Micah Nelson. More top-tier stars will host, including Jennifer Garner, Chelsea Handler, Woody Harrelson, Ethan Hawke, Helen Mirren and Owen Wilson.

Nelson’s innovative songs, unique performance style and jazz-inspired, behind-the-beat style of phrasing, has made the iconoclast one of music’s most widely beloved artists, with 20 No. 1 hits on Billboard’s Hot Country Songs chart. His catalog of hits he penned for other artists includes “Night Life,” “Hello Walls,” “Crazy,” “Family Bible” and “Funny How Time Slips Away.” He earned his first top 10 country hits as an artist in the 1960s with “Touch Me” and “Willingly,” but it was 1975’s Red Headed Stranger that would garner Nelson his mainstream breakthrough. The album’s “Blue Eyes Crying in the Rain” would earn Nelson his first Grammy award, and his first No. 1 hit on the Hot Country Songs chart.

In 1976, Nelson’s music was part of the compilation album Wanted! The Outlaws, which also included Tompall Glaser, Waylon Jennings, and Jessi Colter; the album became country music’s first album to be certified platinum by the Recording Industry Association of America. Nelson and Jennings’ hit collaborations include the 1976, three-week Hot Country Songs chart No. 1 hit “Good Hearted Woman” and 1978’s four-week No. 1 “Mammas Don’t Let Your Babies Grow Up to Be Cowboys.”

A testament to his musical fluidity, Nelson’s albums over the years have paid homage to his Texas honky-tonk roots, but also included projects of pop standards (1978’s Stardust), tributes to Lefty Frizzell (1977’s To Lefty From Willie), Kris Kristofferson (1979’s Willie Nelson Sings Kristofferson), Cindy Walker (2006’s You Don’t Know Me: The Songs of Cindy Walker), Frank Sinatra (2021’s That’s Life) and George and Ira Gershwin (2016’s Summertime), and albums recorded with Ray Price, Roger Miller, Merle Haggard and Webb Pierce.

Nelson was named as the inaugural honoree of the Country Music Association’s Willie Nelson Lifetime Achievement Award in 2012. Three years later, Nelson became the first country artist to earn the Library of Congress Gershwin Prize for Popular Song.

Here, we look at Willie Nelson’s 25 biggest Billboard hits, from “Blues Eyes Cryin’ in the Rain” to “Beer For My Horses.”

Willie Nelson’s 25 Biggest Billboard Hits recap is based on actual performance on Billboard’s weekly Hot Country Songs chart. 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. To ensure equitable representation of the biggest hits from each era, certain time frames were weighted to account for the difference between turnover rates from those years.