The way I see it, he sort of has two sides to his music. There’s the Guthrie-style political protest stuff, and then the Dylan-esque poetic stuff. Both are fantastic.

For political stuff, it kind of depends on what you want to hear since he basically sings the news, but War Isn’t Murder, about the genocide in Gaza, and Red, about the Trump administration, are his top songs. The Great Caucasian God is probably my favourite though since it’s such a good dig at the stereotypical conservative rural American, even down to the style he chose to write in (more of a twangy hillbilly country style, unusual for him typically).

For more poetic stuff, my favourite that he’s published is Malaise, which does still have a couple digs, mostly at Musk (e.g. “will they measure mars in acres?”), but it’s not as outright protest-y as the first few I mentioned. But for his poetic side I actually prefer the stuff he hasn’t published and is just on his YouTube channel, namely Nothing which just came out less than two weeks ago, and Siddhartha. His guitar work on both is great and so are the lyrics.

Both Malaise and Great Caucasian God are from his album Devil’s Den (and he also released With The Devil on the same day, with all the same songs just in a different style, both are excellent), and that’s my favourite album of his. It’s not as political though (aside from the first song), for a more political album from him, Hells Welles is probably my recommendation. The first eight songs off that album are great protest songs, mostly done in a sarcastic manner which is his style (sing from the perspective of the person he’s criticizing).

If you like stripped down acoustic guitar, harmonica and vocals, and aren’t feeling overly political music, Patchwork is great. I’ve got it on vinyl, it’s awesome.

TL;DR check out War Isn’t Murder, Red, and/or Great Caucasian God for political stuff and if you like it check out his album Hells Welles. For poetic stuff, Malaise, and then Nothing and/or Siddhartha on his YouTube channel. If you just want stripped down acoustic music that’s more easy listening, his album Patchwork is great.