Happy Birthday Willie Nelson: 5 of Our Favorite Hits From the Icon’s Smoking-Hot Career & a 50-Song Playlist

by Jim Casey

Willie Nelson is celebrating his 89th birthday today on April 29, 2022. In honor of the Red Headed Stranger’s legendary career, let’s celebrate the Willie Way with five hits. Hit songs, that is (and a 50-song playlist).

With a career spanning more than 60 years, it’s impossible to definitively pick Willie’s best moments. But we’ll give it a go with 5 of Our Favorite Hits.

Now, hit this.

1. Hello, Willie Nelson

Following his discharge from the U.S. Air Force in the early 1950s, Nelson moved to Music City and joined Ray Price’s band as a bass player. Willie scored his first big breakthrough as a songwriter when Faron Young recorded and released “Hello Walls” in March 1961. The song reached No. 1 on the Billboard Hot Country & Western Songs chart in May 1961. Calling the tune a “smash hit” is an understatement. “Hello Walls” stayed at the top of the chart for nine weeks.

2. Nelson Gets the Blues

After dropping more than 30 singles from 1957 to 1974, Willie Nelson landed his first Billboard No. 1 single as a singer with “Blue Eyes Crying in the Rain” in 1975. In addition, the song earned Willie his first Grammy Award for Best Country Vocal Performance – Male in 1975. Willie has since charted more than 20 No. 1 singles with his solo, collaborative, and featured works.

3. Grammy Great

Willie has scored 53 Grammy nominations. That’s not a typo. The Red Headed Stranger has 10 wins under his belt, as well as a Grammy Legends Award and a Grammy Lifetime Achievement Award. In 1980, Willie earned the Grammy Award for Best Country Song for his iconic hit, “On the Road Again.”

4. Willie Is Always Around

Willie Nelson joined forces with Johnny Cash, Kris Kristofferson, and Waylon Jennings to form The Highwaymen in 1985. The super-est of supergroups earned a Billboard No. 1 album and single with their self-titled debut. No matter what happens, The Highwaymen will always be around . . . and around . . . and around.

5. Team Player

Willie is the ultimate team player. Nelson has recorded more than 20 collaborative albums with some of country music’s biggest stars, including Waylon Jennings (Waylon & Willie, 1978), Ray Price (San Antonio Rose, 1980), Merle Haggard (Pancho & Lefty, 1983), and more. The country icon was inducted into the Country Music Hall of Fame in 1993.

High Holiday Playlist: 50 Willie Tunes

Enjoy 50 of our favorite Willie Nelson tunes with this Spotify playlist. Go ahead and put it on repeat today.