3 Pairs of Country Musicians From Different Eras That We Wish Could’ve Joined Forces

If you’re anything like us, a lot of your favorite musicians have either retired from making music or tragically passed away. Consequently, we are left listening to their old records and looking for their sound and wisdom in new artists of the modern day. Oftentimes, that void is filled, and as a result, we want nothing more than to see our favorite old artists collaborate with our favorite newer artists. That being said, here are three pairs of country musicians from different eras that we wish would have had the chance to join forces.

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John Prine & Tyler Childers

In present-day country music, the best songwriter and wordsmith is arguably Tyler Childers. Back in the 1970s and 1980s, that person was John Prine. If you are a fan of Americana or more underground country music, then this pairing seems like a no-brainer. If these two exchanged ideas and made music together, there is no telling what it would be about. However, we very well know that it would move to the utmost degree.

Prior to Prine’s passing in 2020, the two did collaborate on numerous occasions. Furthermore, Childers has mentioned John Prine as a significant influence. So, in a way, Prine and Childers have made music together, as a piece of Prine is seemingly present in many of Childers’ songs.

Billy Strings & Tony Rice

In bluegrass music, the two most tenacious pickers are arguably the living Billy Strings and the departed Tony Rice. If you are a bluegrass fan, then you just might be frothing at the mouth imagining a collaboration featuring these two. Rightfully so, as the world itself might just explode given that it couldn’t handle the speed and intensity of the sound waves being emitted from their guitars. In other words, the work would be an absolute barn-burner.

In 2020, Tony Rice unfortunately passed away, but since his passing, Billy Strings has honored him in numerous ways. Other than covering his songs on occasions, Strings also played Tony Rice’s Martin D-28 guitar during his encores in 2023.

Post Malone & Toby Keith

This might seem like a random selection, and it kind of is, but hear us out for a moment. In the 2020s, Post Malone has arguably been the most entertaining country musician. Now, that might be a hot take, but we are sticking to it. In the 1990s, Toby Keith was in the same boat; thus, we believe a collaboration between these two would simply be fun. Nothing more and certainly nothing less.

Toby Keith and Post Malone never officially collaborated on or off the stage. However, they did once have an impromptu jam session with a bunch of Navy Seals back in 2016. Regardless, we’ve gotten a little bit of a sneak peek, as Malone has covered several of Keith’s songs.

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