One of my biggest regrets is never seeing Elliott Smith live. I guess I should say “in concert,” but “live” works too, in a sad way. I don’t remember how I first heard about Elliott, but I remember having the impression that Either/Or was a classic album before I ever heard his music. I went to the local record shop (yeah, it was a while ago) to check it out. I still remember walking in that day. Shoutout to Volt in Danbury, CT. The person behind the register asked me if I needed help. I said no. I always say no.

I wasn’t planning on buying it, but I was drawn to that cover. That “judging a book by its cover,” thing probably applies to albums too, but try telling that to a kid at a record shop, still clueless about most things in the world. I decided to buy it. As soon as I left the store, I cut the wrapper open with a key, scratching the plastic case in the process, and I put the CD in my Discman. I pressed play. My initial reaction was disappointment. I had no idea that within a year, this would become one of my favorite albums of all time.

On first listen, without knowing anything about Elliott Smith, it’s hard to realize what’s happening on Either/Or. It sounds like a guy, who doesn’t have a particularly good voice, trying to sing Beatles melodies without proper recording equipment or a backing band. It sounds like could-be classic songs completely unrealized. But I was under the impression that this was a classic album, so I kept listening.

When “2:45 A.M.” came on, it wasn’t anything special to me, but I liked that line, “If you’re gonna say shit now, you do it out loud.” As immature as it was, I got a kick out of swearing during soft, acoustic tracks. I can’t even lie, I still do. At the 2:30 mark, the drums kick in, and it’s one of those perfect song moments that immediately and unexpectedly takes a track to the next level. It also ends as abruptly as it comes in. I always wished it would go on for another couple of minutes with those drums and the subtle bass. The fact that it doesn’t just kind makes me like it more. Call it a tease, I guess.

For whatever reason–maybe it was simply because I wasn’t on blogs all day trying to constantly find new music–I kept coming back to that album despite the fact that I wasn’t blown away. I mostly just wanted to hear “2:45 A.M.” Slowly but surely, other songs started to sink in. The lyrics started to resonate. The poor singing started to feel more like an appealing vulnerability and less like a weakness. The songwriting was undeniable.┬áLo-fi, classic pop melodies created by a man suffering incredible pain, with a DIY punk ethos, an acoustic guitar, and–possibly most charming–a fragile voice and shaky, strained delivery. It’s a beautiful thing.

Within months of that blind purchase, it was my favorite album.

Elliott Smith – “2:45 A.M.”

Hit the jump to watch a live performance of “2:45 A.M” and “Say Yes”…

Elliott Smith performing “2:45 A.M” at Irving Plaza, NYC in 1999

Elliott performing “Say Yes” in North Dakota, 1996