At the end of Louis CK’s recent interview in The New York Times, he talks about how Woody Allen went out on a limb to make Take The Money and Run, a mockumentary about a criminal who really sucked at being a criminal. His experiment paid off, and though the studio was apparently angry, the movie was a success. The interview closes with this quote from Louis:

“The reason why I’m able to do what I do is not just ’cause Woody Allen is so cool. It’s ’cause Woody Allen was so successful. Somebody said, you can be a little weird and its going to work out.”

This is the best quote. It’s also the worst quote. Breaking established rules and bucking convention is great if you’re already good at what you do, or at least have some visible, inherent talent. It doesn’t work for everyone except the people that it would probably eventually work for anyway, assuming you believe in destiny, if not, it’s more murky and I’m not sure the logic can be untangled. The point is, it works sometimes and usually has a lot to do with tenacity, if not inherent skill.

Will Oldham is tenacious. As Bonnie “Prince” Billy, as Palace Music, Palace Bros and any number of other confusing aliases, he uses his voice, forever cracked and weary as a way of drawing you in and pushing you away at the same time. Oldham has plenty wisdom to give, but he doesn’t make it very easy to actually get.

In recent years, his records have skewed toward innocuous roots jams. Safe songs that are nice but don’t have the uncomfortable edge that he almost completely abandoned after 2006’s The Letting Go (it’s worth noting that this period has also produced some great material. The Mindeater, his 10″ collaboration with Phantom Family Halo, is particularly overlooked).

To pick one release from Oldham’s darker era is impossible. He’s an artist that inspires a cult following, with fans grafting their own personal experiences onto whatever record of his they happened to be listening to the most at the time. I don’t think this is uncommon, but it is rare to find across an entire catalog.

For me, it’s Palace Music’s 1995 release Viva Last Blues that is an album that teases at greater wisdom. Like much of the Palace-era stuff, the arrangements are loose — chunky piano stumbles over barebones drums and, of course, Oldham’s voice, which is on the verge of breaking, whooping up like gusts of wind and then scurrying back into dark corners, make vague lyrics like “this is what makes a thing last” feel less like broad statements and more like something Oldham is purposefully withholding.

But then there’s “The Mountain Low,” which makes a pretty good case for Oldham’s influential weirdness, starting with the lyrics “If I could fuck a mountain, lord I would fuck a mountain.” It’s a relatively upbeat song that isn’t explicitly played for laughs so much as acting as a sharp intake of breath before “Tonight’s Decision (And Hereafter)” which, like every other time Oldham sings about friends and family on Viva Last Blues involves a lot of desolate loneliness: “And where are my friends, and where is my family, they’ve all gone away though it is I that has left them.”

Oldham never really gives too much away lyrically, but Viva Last Blues feels like an album about willful isolation, about feeling lost and changing our worlds in the hope of finding some kind of truth in new experiences. He makes isolation seem romantic, but he doesn’t shy away from the reality of it either. On the brutal “Old Jerusalem” he sings “Trouble has caused me so much grief, I am waiting for when I can go home/ Time when the room was closer than my friends and I can get some shooting done.” The song spirals into a desperate sort of optimism, and then the album’s over.

There are times when it feels like the best thing you could possibly do is escape the life you’ve made for yourself. Whether or not that’s true is sort of irrelevant. If you don’t escape, you’ll figure out a way to make things better, if you do, you’ll still figure those things out anyway. But that time in between? It’s weird and lonely and terrible when you’re in it, but sort of romantic to think about when you’re not. At his best, Oldham’s albums, particularly Viva Last Blues give us a window into this mindstate. It’s never comfortable, but it’s always worth it.