Why Bruised Orange is the Greatest Prine Album of All Time

An objectively subjective look into a classic album

Welcome to the third entry in what I’m calling “John Prine Week” here at The Song Seekers. John was a favorite of mine and thousands of others and he is missed as much as ever, five years after his untimely passing. Though we miss his presence, we celebrate his music and legacy

I’ve talked about lists on this Substack. In fact I talked about them quite recently. While I like them, they are also often incredibly devoid of any real information or useful applications. Maybe worse than a regular list is the dreaded ordered list. What is best? What is worst? What is in between?

I recently was talking to my friend Rob about the Wilco¹ album, A Ghost is Born, and I declared it to be a top five Wilco album, which got a bit of a chuckle out of him, I suppose because maybe that didn’t exactly sound like high praise, but I have given this some thought and I also keep it vague like that because some days it might slide up to #1 and other days it might slide down to #5. Never will it slide lower though.

My point is that it’s not easy to make favorites lists for artists you love. No one wants to hear that everything is in an exact tie for first. That is both a cop out and unsatisfying and probably sort of disingenuous. But I do reserve the right to maintain a sense of fluidity with my picks. Many factors determine what songs or albums I might prefer at any given time.

John released 13 albums of original material between the years of 1970 and 2018. He also had two duets albums of mostly country covers with female artists and a duets album with Mac Wiseman. There are some live albums too, as well as an album called Souvenirs, which are reworked versions of some of his older songs. I think there’s a Christmas one in there too.

Like Wilco, John Prine has one album that is considered an undeniable classic. In Wilco’s case it’s Yankee Hotel Foxtrot and in John’s it’s his self-titled debut, John Prine.

So basically what this means is, unless you’re deliberately trying to be contrarian or annoying, you’re going to put the classic into your top five, certainly, but really it’s likely to be #1 or #2.

In actuality, of course there aren’t rules to this, but come on now! “Actually, that one is my least favorite because…” When someone starts a sentence like this, I tune out before their reasoning because the sound of my eyes rolling deafens out whatever nonsense they are no doubt spewing. We get it. You’re super cool. But don’t be that guy.

Okay, so we’ve established that John Prine is near the top. It’s my #2. Before I get to #1, let’s talk about the rest of the catalog a bit.

I feel like I need to exclude ‘80s Prine from my ratings. There were only three, but I haven’t spent much time with them. The ‘80s were a tough time for a lot of artists who came up in the ‘60s or ‘70s. I’m not saying they are bad albums, because honestly I don’t know. I skip over them in favor of the gems sprinkled throughout the other four decades of his discography. And there are plenty of gems. I’m looking forward to hearing those ‘80s albums soon, though, during my entire discography listening project. I love those, “Oh yeah! This one!” moments.

I really only recently got into Common Sense and Pink Cadillac, but the latter especially is a bit of a hidden gem. You can read my thoughts on the former in my previous post.

I don’t think there’s a single dud when it comes to his work from the ‘90s onward. He wasn’t super prolific with new material, but everything he did write was stunning. The Missing Years, Lost Dogs and Mixed Blessings, Fair and Square, and The Tree of Forgiveness are all legitimate contenders for my top five at any given moment. Two of them do make my current top five, but as I said earlier, I reserve the right to maintain fluidity with my ratings, so ask me again in about a month and you very well might get a different answer.

You know from my title what my number one is, so let’s not pretend it’s a surprise. Here are the others in my current top 5:

1. Bruised Orange

2. John Prine

3. The Tree of Forgiveness

4. Sweet Revenge

5. The Missing Years

So why Bruised Orange?

While there are moments of excess production, generally speaking the touches are lighter and John and his songs are allowed to stand up front. That’s probably because rather than the producer being a known name or slick pro, it was instead his good friend Steve Goodman. Goodman himself was victim of probably worse overproduction than Prine. The songs on many of his albums are buried in a mess of unnecessary instrumentation and weird mixing and the quality of the songs is lost.

But not here. These are John’s best batch of songs since that storied debut album. “Fish and Whistle”, “That’s the Way the World Goes Round”, and “Bruised Orange (Chain of Sorrow)” are all classics. “Sabu Visits the Twin Cities Alone” is a clever, but slightly bizarre tale of trying to make it as a freak show entertainer past his prime. “Iron Ore Betty” is a fun stomp that fits right in with the rock vibe of his previous two albums. “The Hobo Song” laments the disappearance of the itinerant outsider.

I don’t think the songs are better than his debut. I don’t think that’s possible. But what I do think works here is the songs feel comfortable with one another. John sounds comfortable and confident. The songs flow effortlessly and joyfully into one another. It feels like a cohesive statement. It feels like he’s making the album he wants to make.

I guess it comes down to a feeling sometimes. And it’s really hard to describe a feeling. But this album makes me feel a particular sense of happiness and awe towards Prine’s ability as a songwriter and commutator of relatable human emotions. I just like it. Maybe it’s as easy as that.

And what’s not to like. And that’s pretty much a true statement when it comes to any given Prine album, but there’s a little extra burst of “something” at work. Sorry to be so vague, but I really can’t put my finger on what it is, but I know it’s there. Rich songwriting? Joy? Great musicians laying down great tracks?

All of the above, I suppose. But even that doesn’t encapsulate it. It could be that this album has a more intimate feel to it. It sort of feels like you’re sitting on a front porch with him. Or maybe he’s in your living room and asks if you want to hear a few songs, and of course you would. That earnestness, that easiness, that intimacy…it’s all here. It’s John Prine upfront and honest. Though I don’t think there was another version of John Prine.

So I don’t know. I don’t think I can describe that “something”, but I think whatever it is/was, it’s the reason why so many loved him so dearly and so many miss him so dearly. No one wrote or performed like John and those of us who “get it” really get it. It’s the magic of music. When you have a favorite band, you don’t really have to explain why, you just need to enjoy every moment you have with them.

1. I know, I know. He’s bringing up Wilco again. But you see I have a monthly quota of Wilco mentions I have to meet or Jeff Tweedy revokes my superfan card. He’s firm, but fair, that Tweedy.