Outsider Picks: Best Albums of May 2022

by Clayton Edwards

Last month, I talked about how good this year has been for folk, roots, and country music. A laundry list of great records from April brought that fact into sharp focus. May didn’t have as many killer records. However, this month’s list holds some strong contenders for the best album of the year. At the very least, Zach Bryan’s American Heartbreak and 49 Winchester’s Fortune Favors the Bold will be in that conversation when the time comes. While those albums were the most anticipated of the month, don’t let them overshadow the rest of the list. May brought us some great new albums, and these were the best of the best.

The Best Albums of May 2022

This list contains albums from some of the best independent country artists in the game today alongside some legendary names. Additionally, there’s some great progressive bluegrass and a little western swing to balance things out.

Honestly, the best way to take in these albums is to put them on and absorb all they have to offer. However, I know not everyone has that kind of time on their hands. With that in mind, I put together a musical highlight reel of sorts. Our playlist Outsider Picks: Best of May ’22 has standout tracks from all of the abovementioned records as well as a few killer singles. Check it out below. While you’re at it, be sure to follow Outsider on Spotify to get all the best music from our favorite artists.

Full reviews for some of these albums are linked above. Now, I’m going to dig into some that I didn’t personally cover earlier in the month.

Heartache Kid

Matt Moran’s sophomore album is one of the best examples of great music that flies under the radar. If you’re looking for some sad, earnest country music from a talented songwriter, this album is for you. Moran writes from his heart and his vocal delivery will make you feel his pain, longing, love, and everything in between.

Cruel Country

I joked last week that Cruel Country is the best Wilco album I’ve ever heard. At the time, it was the only Wilco album I’d ever listened to. After doing a little digging, it seems that they’ve always had some country elements in what they did and cranked them up to 11 for this record. However, their indie-rock lyricism and socially-aware themes are still front-and-center. At times, this record makes reminds me of the more country-leaning tunes of the Grateful Dead.

Far Out West Sessions

Flatland Cavalry put together one of my favorite records of the month here. I’m a sucker for stripped-down acoustic arrangements and well-penned songs. That’s exactly what Cleto Cordero and the rest of Flatland brought us with this one. This album feels like you’re sitting around a campfire with some pals listening to good tunes and that’s exactly the vibe I’m looking for going into the rest of the year.