Willie Nelson is more than just a country music icon—he’s a legend whose songs transcend genres and generations. With a career spanning over six decades, Nelson’s unique voice, masterful songwriting, and outlaw spirit have earned him a place in the hearts of millions around the world. Whether he’s singing about love, heartbreak, or life on the road, Nelson has a way of capturing raw human emotion in a way few artists can. His music defies boundaries, blending country, pop, jazz, and even blues, creating a sound that’s unmistakably his. From timeless classics that hit the top of the charts to underrated gems cherished by his most devoted fans, Willie Nelson’s catalog is vast and varied. But which songs truly stand out as his greatest hits? In this list, we’re counting down the top 10 most popular Willie Nelson songs of all time—songs that have not only defined his career but also left an indelible mark on the world of music. Whether you’re a lifelong fan or new to his work, these tracks are essential listening for anyone who appreciates the artistry of one of America’s most beloved musicians. Get ready to take a trip through the very best of Willie Nelson!