Longtime friends Waylon Jennings and Willie Nelson wrote ‘Good Hearted Woman’ while playing a poker game in 1969. Jennings spotted a newspaper ad promoting a Tina Turner concert that stated, “Tina Turner singing songs about good-hearted women loving good-timing men.” Waylon and Willie jokingly admit that they wrote the song with their own wives, Connie and Jessi, in mind. Waylon released the song as a solo recording in 1972, then re-released the song as a duet on the album ‘Wanted: The Outlaws’ with Willie Nelson in 1975.

When ‘Beer for My Horses’ shot to No. 1, Willie Nelson made history with his duet partner Toby Keith. Up until this time, Kenny Rogers had held the record for the oldest person to have a No. 1 Billboard country hit at the age of 61 with ‘Buy Me a Rose.’ Three years later, at the age of 70, Willie Nelson rode to No. 1 and grabbed the title as country music’s senior chart-topper. The song later inspired a movie starring Toby Keith, Rodney Carrington, Ted Nugent — and of course — Willie Nelson.

Emmylou Harris originally recorded ‘Pancho and Lefty’ on her ‘Luxury Liner’ album. Nelson’s daughter Lana made him aware of the song while he was working on a duets album with Merle Haggard. In January of 1983, the album’s first single ‘Reasons to Quit’ landed at No. 6, and by spring, ‘Pancho and Lefty’ soared to No. 1. Nelson would team with Haggard for another duets album in 1987. The two would later join forces with Ray Price for the ‘Last of the Breed’ album and tour in 2007.

In 1982, Ray Charles was working on a country project with Columbia Records when the idea came about for the album ‘Friendship,’ pairing Charles with established country singers like Ricky Skaggs, Hank Williams, Jr. and the Oak Ridge Boys. ‘Seven Spanish Angels’ was originally pitched as a duet with Ronnie Milsap, but it didn’t quite work out. In the meantime, producer Billy Sherrill found out that Willie Nelson liked the song and was willing to cut it for the duets album. In 1984, Nelson landed yet another No. 1 duet. The song was also included on his own album of duets in 1985, titled ‘Half Nelson.’

Legendary songwriter Steve Goodman wrote this song after a train ride to meet his bride’s grandmother in Illinois. They rode on a train called the City of New Orleans, and as they passed the scenery, Goodman was inspired to write the song. After learning that the train would be shut down unless ticket sales increased, he pitched the song to Arlo Guthrie, who made it a hit in 1972. Wille Nelson’s 1984 version of the song chugged to the top and earned a Grammy for Country Song of the Year. Goodman was also the songwriter referenced in David Allen Coe’s hit, ‘You Never Even Call Me by My Name.’

Out of all of his great compositions, the country music hall of famer cites ‘Angel Flying Too Close to the Ground’ as one of his all-time favorites. Nelson wrote the song while he and his wife Connie were dealing with marital problems in 1976. Released as the second single from the soundtrack to the ‘Honeysuckle Rose’ film, the song shot to No. 1 in 1981. In the Warner Brothers picture, Willie Nelson starred as Buck Bonham, an aspiring singer struggling to make it in music and keep his family together. This early ‘80s classic is a must on our list of the Top 10 Willie Nelson Songs.

Willie Nelson has held the record for charting more duets than anyone else in country music history. In 1984, he paired with the most unlikely of duet partners. While on tour in London, Nelson and his wife Connie heard Julio Iglesias on the radio and Willie liked his sound immediately. The country crooner tracked down the Latin superstar and pitched the idea of recording ‘To All the Girls I’ve Loved Before.’ On its way to No. 1 on the country charts, it sold over a million copies, peaked at No. 5 on the pop charts, and eventually won honors from both the ACM and CMA awards.

https://www.youtube.com/watch?v=ZqryIcn3Nl0

‘On the Road Again’ is easily considered Willie Nelson’s signature song. On a flight together, Nelson was asked by the producers of the ‘Honeysuckle Rose’ film to write a song about touring to be used as the movie’s theme song. By the time they had landed, the lyrics to ‘On the Road Again’ had been composed. The song rolled up to No. 1 in 1980 and earned a spot in the Grammy Song Hall of Fame. At the age of 78, Willie is still rolling down the highway on his bus ‘Honeysuckle III’ — he wore the other two tour buses with his massive amount of touring.

In 1982, Willie Nelson recorded his own version of the already-recorded ‘Always on My Mind.’ The song was released by Brenda Lee in 1972, Elvis recorded it as the B-side of 1973’s ‘Separate Ways,’ and John Wesley Ryles cut a Top 20 version in 1979. Originally pitched to Willie while he was working on a duets album with Merle Haggard, the two passed, thinking it sounded better as a solo recording. Nelson released the song in 1982, and it was later awarded with multiple CMA, ACM and Grammy awards. The song that placed Willie Nelson at No. 1 for two weeks is a given on our list of the Top 10 Willie Nelson Songs.

Willie Nelson placed his first song on the Billboard country charts with ‘Willingly’ in 1962. Although he was having success as a songwriter with cuts from other artists, his own records were not well received by radio. Most of these records were slickly produced with lush orchestration and background choruses. Finally, in 1975, Willie Nelson found the song that would better suit his own style. Stripped down to just his unique voice and acoustic guitar, affectionately known as Trigger, Nelson hit No. 1 for the first time with ‘Blue Eyes Crying in the Rain.’ A groundbreaking recording penned by Fred Rose and originally cut by Roy Acuff, this Grammy winner is a perfect fit to represent the hits of Willie Nelson at No. 1.