9 Perfect Willie Nelson Karaoke Songs

Willie Nelson is still one of the most incredible musicians that has ever been on the scene. He has written some wonderful songs that others have sung, but he is also very well-known for his own stunning and very unique voice that has made a bunch of songs classics. His songs have always had a special place in my heart as these memorable stories that he tells through music. For many of us they have always been a part of building core memories. 

When it comes to karaoke night, Willie Nelson’s songbook is jam packed full of classics that would be awesome songs for your karaoke night playlist. Let’s look at some of the best Willie Nelson songs for karaoke. 

1. On the Road Again

We have to start off with one of his biggest hits ever. “On the Road Again” is not only a really popular song, but one that will be really fun to sing for karaoke night. You don’t have to have experience with living on the road to enjoy singing this song and really getting in the spirit of this music. 

It was one of the songs that appeared on the soundtrack to his film Honeysuckle Rose. But the song was a much bigger hit than the movie. It has a pretty funny story attached to it. Willie Nelson did not write this song when he was on the road, in fact he was high in the air at the time, on a plane. He wrote the entire thing on an airsickness bag while mid-flight. 

Despite the song’s humble and slightly strange beginnings, it was still a massive hit. And one that quickly became a classic. Possibly because he told the story of his experience on the road. 

2. Bloody Mary Morning 

This song has a bit more edge than a lot of the other songs that Willie Nelson has released. So, it is the Willie Nelson song if you like a song with a bit of a harder edge, for example rock songs. Then it might be the perfect choice for your Willie Nelson karaoke night. 

He was going through a pretty hard time when he released the song, his marriage was failing, he had a music contract that was not really lucrative and he was really rethinking his next move musically. It took him a moment for someone to really take notice of the song, but it did eventually give his career a much-needed boost. 

3. Roll Me Up and Smoke Me When I Die – with Snoop Dogg, Kris Kristofferson and Jamey Johnson

Want a bit of a hip hop or fun vibe with your country music? Then this just might be the song that you want to add to your set list. 

This might not be the group that you would ever put together in a song, but somehow it just really works and creates an incredibly fun upbeat song that isn’t quite like anything else in the Willie Nelson songbook. 

It is a song that does show off a certain favorite pastime that some of these men have in common but the word for the song is fun. Nelson performed the song on the day that a bronze statue of him was unveiled. He joked at the time that he would be “stoned” for “one thousand years”. It works great for his persona. 

This would be the song to sing at karaoke night with a bunch of your friends who all enjoy making a bit of a joke with the performance. No one that takes themselves too seriously could pull this one off. 

4. Always on My Mind 

We might know the Elvis version of this song a little bit better but Willie Nelson won three Grammys with this song. Nelson got the song when he was in the studio recording another album. “Always on My Mind” was pitched to Merle Haggard who passed on it. 

Nelson quickly claimed it and very soon after he recorded the song. It was a great move and worked for him. And it can work for you too to make karaoke night really memorable. 

It doesn’t really matter if you are channeling Elvis or Willie Nelson, both versions were great. They were really lovely love songs that had that little something special. 

5. Mammas Don’t Let Your Babies Grow Up to Be Cowboys 

This is probably one of the biggest classics when it comes to Willie Nelson songs. It represents everything that he sings about in all the other songs. He doesn’t ever say that cowboys are the bad guys, but he does hint to that in a few different songs. 

But surprisingly this song that is so very much the ultimate Willie Nelson song was not actually written by him. It was already a hit for Ed Bruce who was the author and had also been covered by Chris LeDoux before Willie Nelson and Waylon Jennings got hold of the song.

Related: The Best Johnny Cash Karaoke Songs

After Nelson and Jennings sang “Mammas Don’t Let Your Babies Grow Up to Be Cowboys”, their version was pretty much the only one that people could recall. It had all of the feeling of the dark cowboy mood with the mischief that Nelson’s voice also brought to the song.

It is an awesome song to sing on karaoke night if you want to go with some old school country that has a dark side. 

6. Crazy 

This one is a great example of the amazing songwriter that Willie Nelson has always been. He was well known as an incredible songwriter long before he became known for that special voice. He wrote “Crazy” and hoped that the Grand Ole Opry member Bill Walker would sing the song. But that didn’t work out since Walker felt that the song was too feminine. 

That didn’t stop Nelson and he decided that he would take the advice and pitched the song to Patsy Cline. It worked out pretty well as her version became an instant classic and a ballad that even now is hard to resist singing to. 

Related: Best Country Karaoke Songs for Women

Why resist at all? “Crazy” is a great ballad for karaoke night. It is more of a slowed down song than some of the others on this list with less instrumental accompaniment. So, you do need a pretty clear voice to sing it. 

On the question of whether or not this is a song for a man or a woman to sing, it doesn’t really matter. Nelson released his own version later and it was pretty awesome too. Despite having a much different feeling from Cline’s. If you love the song, then go for it. 

7. Mendocino County Line -with Lee Ann Womack 

If you are looking for a great duet to sing with a partner, then this Willie Nelson song could be the perfect song to feature on karaoke night. 

It was a song that showed that Willie Nelson still had it and is just beautiful. It is all about a love that couldn’t last. Womack’s soaring voice gave the strength to the vocals and then Nelson brought all the nostalgia and made the song seriously poignant. The song was so good that it even won the Grammy for Best Country Collaboration. 

This song works well with two very different voices, as long as you can feel some of the pain in the story you should be able to pull it off on karaoke night. 

8. Angel Flying Too Close to the Ground 

This is the song to sing for karaoke if you can keep it together during a sad song. Or if you are happy to show emotion on stage then this could be the one that allows you to get any feelings out that you might be dealing with. 

The song was written by Willie Nelson as another addition to his Honeysuckle Rose soundtrack. It did really well in the country charts, but it was also intensely personal to Nelson. During some of his live performances he would dedicate “Angel Flying Too Close to the Ground” to his son who died from suicide in 1991. 

It is a beautiful song to sing if you are up for singing something that has sad lyrics and a haunting tune. 

9. Half a Man 

For a long time, Willie Nelson was not very well-known even after he wrote many different hits for other singers. This was the song that started to change that. 

“Half a Man” sounds like a sad love story about a man that has become “half a man” thanks to the betrayal of a woman. But the real story is a lot weirder and more interesting. It might just shatter some of the ideas you have about this song. 

It was inspired when Willie Nelson woke up in the middle of the night and he wanted to smoke a cigarette. The only problem was that his arm was around a woman who was asleep and he couldn’t get up without waking her up. 

It made him think how it would be if he only had half of his body, and that is what led to this song. A craving for a smoke and being pinned by a lady. Still, it sounds like a great love song and will fit perfectly into karaoke night. 

Plan Your Willie Nelson Karaoke Night Now

Willie Nelson has written and performed some amazing songs. You could plan an entire karaoke night around his music. Start creating your playlist today. 

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