From fabled singer-songwriter to ’80s and ’90s hitmaker, John Anderson has done it all in country music.

He helped build the landscape of the genre, literally: When Anderson first moved from his home state of Florida to Nashville, Tenn. in 1972, he got a job as a construction worker and was contracted to build the new Grand Ole Opry house.

The singer-songwriter and country performer first began to see success in the late 1970s, when his single “The Girl at the End of the Bar” broke into the Top 40 on country radio. He went on to chart more 40 singles over the next decades, and landed five No. 1 country hits, including country staples such as “Straight Tequila Night” and “Swingin’.”

You’ll find both those mega-hits — and many more of Anderson’s commercially successful songs — on this list of his 15 best songs. But this assembly also takes his deeper cuts into account. In addition to finding major success as a performer, Anderson also achieved significant acclaim for his nuance and depth as a songwriter. That talent for emotional delivery only deepened with time and age, and he was inducted into the Nashville Songwriters Hall of Fame in 2014.

His most recent studio album, Years, came out in 2020, and at the time of its release, it was the first project full of new material that Anderson had released in five years. He wasn’t rusty, though: If anything, that album offered some of his most tender and emotionally varied musical moments to date. Its title track even earns a spot in the Top 5 on this list.

Read on for a primer on Anderson’s storied career, and a diverse list of songs that prove point blank that he’s got decades’ worth of music proving why he belongs in the Country Music Hall of Fame.