There are moments in life – decisions you make and crossroads you take – which end up leading you down incredibly interesting paths. Often times, these decisions can take years before you realize how much of an impact a certain moment had on your life.

Sometime in 1991, a friend of mine and I walked into the Quonset Hut, a record store located just north of Akron, Ohio about 15 minutes from the Kent State campus. The memory is still so crystal clear to me. As soon as I got in the store, I knew whatever they were playing on the store speakers was an album I absolutely had to have. The clerk informed me that the album being played was Teenage Fanclub’s Bandwagonesque and the song playing was “December.” Both that album and that song remain some of my favorite music today. “December,” in fact, ended up on a CD that Stephanie and I put together for our wedding and gave out to people who attended. That moment, while I did not know it at the time, turned out to be quite a pivotal few minutes in my life. The door flew open and bright light shined in – here was music that I never heard before and would never get played on the radio and I just fell in love with the song. I would go on to find much more and it lead me eventually to start my own label, all for the purpose of trying to expose music that wouldn’t have a prayer of being heard on the radio. Ah, so young, naive and noble.

A few months later, that same friend and I made our way up to Cleveland as Teenage Fanclub were on their tour of the U.S. for Bandwagonesque. It turned out to be a night of firsts. It was, in fact, the first time I had ever seen a band in a nightclub and not an arena. It was also the first time I saw a band called Uncle Tupelo, who were the opening act on this tour. I had known about Uncle Tupelo and even recalled liking the records they had out, which I had heard at the college radio station when I worked there.

Truth be told, my friend Lance and I were not totally blown away by UT when we saw them. I recall there being discussion about the scraggly trio as a group that was pretty much a loud version of R.E.M. Their power was evident, though.

It turned out to be a pretty excellent show. Two years later, Tupelo released Anodyne, an album which did actually change my life in many, many ways. It was one of the many moving pieces that all came together after college and put me on a completely different track – from wanting to work in television production trucks to wanting to work in the music business. Anodyne wasn’t the sole reason, but it played a big factor in my decision at the time to pursue work in the music business and ended up defining the rest of my decade. It was that important. But that’s a story for another time. For now, it was that moment in Ohio in 1991 when I walked into the Quonset Hut and I heard that sweet song – that’s what set things into motion.

That’s why today’s edition of Item Five seems so incredibly special to me. Melodramatic? Maybe. But being able to interview Uncle Tupelo/Son Volt frontman Jay Farrar was just really exciting for me. Not because I put “famous” people up on a pedestal, but because something he did, the art he helped construct, ended up being such a profound reason for where I am today and what I believe about music. It can change your life if you let it. Plus, Anodyne is one fucking great album and Jay Farrar doesn’t follow fame or money, he seems to follow what’s important to him. As a songwriter, he’s right up there with the best. Both Uncle Tupelo and Son Volt are no longer making music together, but Farrar has soldiered on as a solo artist with two solid albums. His live shows continue to be captivating, both for the performance itself and his flat-out superb choices of cover songs.

So it’s with great excitement on my end that he actually agreed to do this – to be subject to my sometimes ludicrous line of questioning. As it turns out, and I am not one to brag, I think this is the best interview I’ve ever read with the guy. So there.

1. You seem to have a geniune fondness for old buildings (“Way Down Watson”) and a sadness when they come down. Where does that come from? Do you just like old buildings or is it more the passing of time or certain era’s??

There was an old motel on Watson Rd. (old Route 66) called the Coral Court Motel that I actually stayed at once or twice. Each room was a stand alone building with it’s own two car garage. The buildings exuded a sense of being in another time. The artistry involved made the place stand out in a sea of homogenized new homes and strip malls.

2. Which of these lyrics (all yours) do you like the best and why?

a) “there’s a beach there known for cancer waiting to happen”

b) “will bad water mix with blood, to make the hollow man decide”

c) “silver spikes and mace displayed in your eyes”

The only lyrics of mine that I like are the ones that I haven’t written yet. I generally like the ones that are the least literal.

3. This is probably my only chance. What is “Fifteen Keys” about?

I think the point of origination for that song was from traveling and doing shows with a pocketful of keys that you realize are useless until you get home. I’m now down to about 10 keys.

4. A lot of articles claim that you don’t do email or look at the internet, yet I am clearly debunking that by doing an email interview with you. What gives? Why do people assume such things?

I don’t know. I guess since my profile is non-existent on the chat-room/message board circuit people assume that I am a Luddite. I couldn’t live without e-mail or the internet.

5. I saw Uncle Tupelo for the first time when you opened for Teenage Fanclub in Cleveland on Valentine’s Day in 1991. At the time, it was two of my favorite bands and I’m not sure I’ve seen a better (or stranger) pairing. Did you feel the same way at the time?

On the surface it may have seemed like a strange pairing but it really wasn’t. There was a commonality of purpose. We were just coming at it from slightly different directions.

6. I bought a Teenage Fanclub shirt that night, not an Uncle Tupelo shirt. Do you care? I feel bad in retrospect, because you could have really used the money and if I could have, I would have bought both shirts. But I was in college, kinda poor and the Teenage Fanclub shirt had a picture of Casper the Friendly Ghost on the back.

Don’t feel bad. Maybe we could have used the money but you can’t argue with Casper the friendly ghost. We traded shirts with those guys and we came away with the ones that said “Teenage Fucking Fan Club”.

7. Who is the most underrated band of all time, in your opinion?

I couldn’t pick just one. The Flamin Groovies, Q65, Badfinger, The Sonics, The Pretty Things

8. Who was the first band you were completely obsessed with?

The Beatles and then the Rolling Stones.

9. What is the last thing you really laughed hard at?

A Confederacy of Dunces about 15 years ago? No. The last thing was probably Mr. Show or Curb Your Enthusiasm or Ali G.

10. Your last couple of albums have largely been acoustic-based. Tell me about plans for the next album – when it might be out, will it be more electric or along the same lines?

I seem to naturally gravitate to the acoustic guitar when I write. I think to a certain degree it allows for more flexibility in that the song can wind up electric or acoustic. I’ve been away from the electric guitar for awhile so I expect to get back to it at some point.

11. Why don’t you ask me a question?

Who is an Australian’s worst nightmare?

Jeff’s Answer: Oh lord. This is the toughest question I think anyone’s asked me yet. I feel like this is a riddle, or that there’s actually a right answer. Hmmm…..let me see. I would have to say the Reggie Jackson candy bar. First off, Reggie was a weird looking dude, even for the 1970s. The fact that he actually had a candy bar on the market was incredibly American, but Australian’s must have been horrified. Yes, that’s it. The Reggie Bar.

12. You have two children – have they ever listened to any of your music? What has their reaction been?

They often request to hear music that I’ve done. I hope it doesn’t scar them! They usually either want to listen to my music or Steve Burns’s (Blues Clues) though one of them has now turned on Steve.

13. “Dent County” might be the best song you’ve ever done, in my opinion. Did your mom & dad get to hear it or was it written after your dad passed? Do you ever get emotional while writing and performing songs like that?

I was writing “Dent County” during the last couple of months of my Dad’s life and finished it and recorded it several months later. It’s hard not to get emotional when writing a song like that.

14. I just got married – any advice?

You’ve got what— like a 44% chance? Good Luck!

15. If you had to choose, who would you rather be: Michael Moore, Martin Scorsese, Woody Allen or me?

Let’s see. Michael Moore has made some very good films and he sells out soccer stadiums in Germany. Martin Scorsese has done some of the best films of our time. Woddy Allen has been consistent over the years making good films. You’ve got a kick ass web log. I would choose to be you because you get to ask questions like this instead of answering them.

A big thanks to Jay Farrar. One other note: this is actually the first interview I’ve done where I didn’t have to edit a single thing. No caps, no scary grammatical errors, nothing. Kick ass. Kick ass!

Song now playing: Spoon – “Something To Look Forward To”