Beer For My Horses (Duet with Toby Keith)
Chart-wise, Willie's biggest hit came as a result of a collaboration with Toby Keith. The single spent six weeks on top, and an amazing 39 weeks on the chart altogether. It was his first number one since 1989, and the success of the song gave him – at age 70 – the distinction of being the oldest artist to top the Hot Country Songs chart.
Mamas Don't Let Your Babies Grow Up To Be Cowboys (Duet with Waylon Jennings)
The biggest hit of the Waylon and Willie partnership was actually a cover – of a top-20 1976 single from Ed Bruce, who co-wrote the tune with then-wife Patsy. However, the two leaders of the "Outlaws" made musical history with their version, which spent a month atop the charts – and also netted the duo a Grammy.
Good Hearted Woman (Duet with Waylon Jennings)
Incidentally, Waylon and Willie's second biggest hit together was also a cover – sort of. Though the two wrote the song together – in the middle of a poker game, Jennings recorded the song first, taking it to No. 3 in 1972. However, it was their 1975 duet of the song that would help to define the "Outlaw" era, and also won them a 1976 CMA Single of the Year trophy in the process.
To All The Girls I've Loved Before (Duet with Julio Iglesias)
One of the most unlikely duet pairings of Nelson's career turned out to be one of his biggest worldwide hits. The 1984 single became a breakthrough moment for Julio Iglesias in the English-speaking market, and was one of only two Nelson singes to be certified platinum.
Blue Eyes Crying In The Rain
It's somewhat ironic that the first number one from Nelson was a cover. After all, he earned his first stripes in Nashville writing such hits as "Crazy" and "Hello Walls." However, the song that broke Nelson to the mainstream world as a vocalist was a 1940s chestnut from the pen of Fred Rose – who passed away twenty-one years before Willie put this one at the top.
Always On My Mind
Brenda Lee had done it. Elvis Presley had too, taking it to the country top-20 in 1973 on the heels of his divorce from Priscilla. However, Nelson's version became not just a country chart-topper, but a pop classic, as well – peaking at No. 5. The song also netted back-to-back CMA Song of the Year statuettes for writers Mark James, Johnny Christopher, and Wayne Carson in 1982 and 1983 – making it only the third song to win the award twice. Nobody has done it since.
Just To Satisfy You (Duet with Waylon Jennings)
of their chart-toppers as a duet, the song actually had been around for years. Jennings wrote it with Don Bowman back in 1963, and had recorded it a couple of times in the 1960s, with Bobby Bare recording a version as well. With a little bit more tempo than the original, the duet recording hit number one on the charts on May 22, 1982 – knocking the afore-mentioned "Always On My Mind" out of the top slot – a rare occurrence in country music that an artist has knocked themselves out of the top spot!
My Heroes Have Always Been Cowboys
Written by Sharon Vaughn, this song gained widespread attention for its' inclusion on the soundtrack of The Electric Horseman. On March 8, 1980, it became yet another chart-topper. The original artist to record the song? Waylon Jennings.
Seven Spanish Angels (Duet with Ray Charles)
In 1984, it seemed as if the entire Columbia / Epic roster was lining up to record a duet with Ray Charles on his album Friendship. It seems that Nelson got the pick of the litter with this tragic story song. It hit number one in the spring of 1985, and gave Charles his biggest country hit, as well.
City Of New Orleans
Written by Steve Goodman in 1971, many artists recorded this song over the years – including Judy Collins, Johnny Cash, and Jerry Reed. Nelson's version hit the top in November of 1984 – less than two months after Goodman's death from leukemia. A few months later, Nelson's version would net Goodman a posthumous Grammy Award for Best Country Song.