Willie Nelson Live Performances Everyone Should Know

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Willie Nelson is hosting the Heartbreaker Banquet at this year’s SXSW, and to celebrate the event, let’s look back at some of his finest live performances. Nelson has been making music in for nearly six decades now, and in that time, he’s given us plenty of memorable in-concert moments. These are some of the absolute best.

Crazy (1992)

“Crazy” became an enormous hit for Patsy Cline, who recorded it in 1961, but it was written by Nelson, who gives a stirring performance of it here at a concert with The Highwaymen, a supergroup that also included Johnny Cash, Waylon Jennings, and Kris Kristofferson. While Cline’s recording became the most famous version of the song, Nelson has been playing it live for five decades now, and it remains one of the highlights of his set list.

“On the Road Again” (US Festival 1983)

Ah, the US Festival. Homer Simpson once claimed that it was the greatest music festival of all-time (“It was ran by that guy from Apple Computers.” “What computers?”), and if this fantastic performance of one of Nelson’s biggest hits is any indication, he might be right. Nelson was 50 years old during this performance, and as you can tell, he was just hitting his prime.

“Blue Eyes Crying in the Rain” (The Midnight Special 1980)

Willie Nelson’s big break came in 1975 with the release of his massively popular album The Red-Headed Stranger (as Marge Simpson pointed out, “You just don’t say ‘no’ to the red-headed stranger”), which gave him his first No. 1 hit on the country charts with “Blue Eyes Crying in the Rain,” which he gives a brilliant performance of here on The Midnight Special in 1980. Also, if you’re up for a real flashback, check out the introduction he gets from Captain & Tennille. I think it’s fair to say this song has held up a bit better than “Muskrat Love.”

“Always on My Mind” (Farm Aid 2014)

This one serves as a reminder that Nelson has remained an incredible performer even into his ’80s, which is why his SXSW performance should be something special. In this clip, he delivers a moving version of what may be his most famous song (even the Pet Shop Boys covered it!), and he sings with the same conviction as when he originally recorded it.

“Georgia on My Mind” (Duet with Ray Charles – 1986)

After have a huge success with The Red-Headed Stranger, Nelson’s hot streak continued with 1978’s Stardust, an album which featured covers of many famous songs, including this Ray Charles classic. During his 1986 special, he invited Charles to perform the song with him, and the two produced a beautiful duet at the piano. It was a fantastic performance by the people responsible for the two most famous versions of a legendary song.

Woodstock ’99

Woodstock ’99 is probably best remembered for being a mixture of terrible nu-metal and rioting, but it wasn’t all bad. Willie Nelson put on a fantastic set which you can watch in its entirety here. Other than his association with weed culture, it’s hard to know exactly why he was chosen for this event, but in any case, he was certainly one of the better performers on the bill.