Picture of Ann

This is the cassette I found in a box of old tapes.

It’s amazing how finding one small thing can make you realize so much about your life, past and present. For me, the small thing was a cassette tape. Remember those? It was in a shoe box with twenty or thirty others. No, it wasn’t a mixed tape that someone made for me. It wasn’t an oral history of a long dead relative. It was me. Twenty years ago.

Back in the late eighties and early nineties, I made a go at being a singer/songwriter. My goal was to make some demos, get a record deal and then, well, I hadn’t really thought much farther ahead than that. Making a demo was much harder then than it is now. In those days, the idea of recording onto computers was as alien as, oh I don’t know, carrying a tiny telephone in your pocket that also takes pictures and plays music.

Back when I was young-I still have that guitar!

By 1992 or so, I had managed to attract a small following by playing places such as The Towne Crier Cafe and The Turning Point. I’d gotten some airplay and interviews on WFUV and WFDU, two local college stations.

My Dad was a staff engineer at Columbia records and decided to help me out by making a demo with “my band”. My band consisted of a trio of older guys who liked my songs and decided to pitch in as well. Here’s a tip for younger musicians: play with older musicians any chance you get. They’ve heard it all, they’ve played it all and you’re probably not showing them anything new. You’ll learn a lot and your songs will sound better because of their musicianship. I was really too immature to appreciate this.

Here's another press photo from 1989. There wasn't a lot of traffic.

Anyway, one Saturday my dad, the band and I gathered in a high school gymnasium in Connecticut to make a demo. We recorded the band and me live to two track DAT (remember those?!). There were no overdubs, no punch-ins, no nonsense. We just played and Dad pressed record.

Twenty years later, I’m scrambling to find a cassette player that works. OK. Got one. It was out in the garage. I patch it into my mixing board, press play and bring up the faders. Holy crap. The instruments sound great. The playing is tight. The mix is clean, nothing is hidden. They were all pros, my Dad and the guys.

But then there’s me. Not a pro. Not then. That’s clear. I’m the weakest thing on this recording. I mean, the guitar playing is pretty good (I’m the acoustic guitar on the right) but my voice seems to have a pretty tenuous relationship with pitch and isn’t particularly expressive. If I was a record exec and heard that voice, I would’ve passed also.

So why did they do it? Why did my Dad and these guys go out of their way to help me out? What I remember them saying is that they liked the songs, which brings me to, well, the song. I wrote “Picture Of Ann” about a girl named, not surprisingly, Ann.

Short story: I liked her. I asked her out. She stood me up. A few times. Why would I let someone do that? Well, if I had a picture of Ann, I’m sure you’d understand.

Ann is now a mom with two kids, one of whom has been my assistant at one of the historic sites where I perform. Ann has an entirely different memory of the events that inspired her song. Doesn’t matter now.

I think this old tape may have stretched a bit. It seems a little slower than I remember. I hope you enjoy the song. You can listen here:

Picture Of Ann (1991)