On the way home after work tonight, I played the usual Monday Night Game.

Should I go out? Or shouldn’t I?

I work late on Monday nights (til 8PM), so the night is shot anyway. And Monday night is Showtune Night at Sidetrack, my favorite hangout in Chicago. More than likely, I’m bound to find at least a few chorus boys there.

So the dilemma always presents itself. Should I go out, or shouldn’t I?

Well today I had driven in to work, because I had a doctor appointment in the morning. So on the way home, I told myself (as I often do when this situation presents itself) I will drive down Halsted Street from Belmont going north toward Sidetrack. If I find a parking place, I’ll take it and go out. If I don’t, I’ll go home.

Lo and behold, I found a parking spot, less than a block away from Sidetrack. Guess I’ll be going out for a bit.

It’s about 9:30. Showtunes had started, but it was still way too early to be there. The place was pretty empty. So I checked my coat and decided to go across the street to Roscoe’s. I generally never go to Roscoe’s, but I knew there would be someone special there tonight.

Monday is Amy and Freddy night.

Now, those of you from Chicago know who I am talking about. Amy Armstrong and Freddy Allen. They’ve been entertainers in the Chicago area for the better part of the last 10 years or more. I befriended them a few years ago when she was performing at Gentry, a piano bar on Halsted Street.

The story goes like this.

I was there with the Chorus, after rehearsal, for one of our “alternate bar” nights. Gentry was hosting us and Amy and Freddy were performing.

Amy was just finishing a weeklong stretch of shows, and was admittedly pretty tired. She said so. So she said “Alright, you chorus boys, get up here and sing some songs. I know you can do it, so do it.” She’s bossy like that.

So a few of us obliged. Myself included.

If I remember correctly, I sang “Bridge Over Troubled Water” and “Sittin’ On The Dock of the Bay”. In any case, I ended up doing two numbers.

Amy cornered me and said “You have an amazing voice… have you ever thought about singing at Gentry or something like that?”

I replied, “Yeah, but I never really gave it any thought, to be honest.”

Amy said “Come with me.” She led me to the back of the bar, and introduced me to the owner of the bar, who just happened to be there that night. “This is Dave. Dave, this is Rick. And Rick should be singing here.” Dave shook my hand and said “Nice to meet you” and all that… and asked me if I’d be interested. I said “Sure I would, I’ve always wanted to.”

When we were done with Dave, Amy pulled me aside and said “Here is Dave’s number, and here is my number. You’d better do this!”

Well how could I say no?

Within a couple months, I had my first show at Gentry.

Amy and I got together a couple of times before that and talked about shows and songs, and one day I went with her and her husband to the Chicago Public Library to find music. By the time we were done there, I had amassed a pretty large collection of music for my book.

I became a regular at Amy’s shows, and she would occasionally pull me up to do a song or two, saying that I was going to have a show of my own there soon.

My first show was a Tuesday night. Tuesdays are open mike nights at Gentry, and I got the gentleman who plays on open mike nights to play for my show. My shows were always from 7:30 – 9:30. The late shows (which I never did) were from 9:30 – 1:00 AM.

The first show was essentially a dry run of things. I had a list of songs I wanted to do, there were a few friends in the audience, and I tried out some banter with them. It was rough. VERY rough. But I got through it. And made a little money as well.

The second show was on a Saturday night. I had Emailed the entire Chorus about it. And I knew a lot of people were coming. My sister and her (then) fiance were coming. This was the “big show.”

Freddy Allen played for me that night. That helped my nerves a bit, since I’d sang with him before and I felt comfortable with him there. The show was a ton of fun. I sang my heart out, bantered with the audience, and had a blast. I was on my way!

As the next year rolled on, the shows would vary between a nearly empty bar to a fairly busy crowd. But never anything like the first night. I kept working on the show, trying to build something around the songs I’d picked and making things somewhat cohesive. But always trying to have fun.

The problem I ran into was that I could never hold on to an accompanist. I think I went through five fairly regular accompanists and a couple real disasters in the course of a year. Just when I would be able to find a groove with someone, they would tell me that they couldn’t do a month of shows, or that they just weren’t interested in playing the bar anymore. Each month became a hunt for a new pianist. It became a chore rather than something that I enjoyed.

And then in April of 2001, I started my current job. I knew that I wasn’t going to have the time available anymore.

So my brief career as a cabaret performer ended.

I really enjoyed it though. I love to sing, and whether I get paid for it or not, I will always be able to find a way to do it. Someday I’d love to get back into that arena, but I’d probably do a few things differently… one of which would be to find someone to play for me before I go for it.

But it was a dream that did come true for me. And I have Amy Armstrong to thank for that.

Amy left Gentry to start performing at a new club called “Voltaire.” It was a great idea, and had a great run of shows, but numerous issues led to the club’s closing late in 2002. Amy and Freddy then moved on to do shows at various bars and clubs, and continued back on doing some touring, which she always loved to do. I’d seen her a time or two at her new Monday night show at Roscoe’s, but it’d been a good year or so since the last time.

So when I saw her today, she looked right at me and said “No WAY! Oh my GOD!” And gave me a huge hug. Oddly enough I had brought her up to someone at work today, and she said that she had just thought about me the other day as well. So somehow there was a reason why I showed up there that night.

She gave me one of her new CD’s. She insisted that I not pay for it, but I slipped an extra $10 in the tip jar anyway.

The CD is fabulous. I love it. I listened to it on the way home tonight. It made me feel, once again, the reasons why I loved singing so much.

So this is my little paen to Amy. Amy the diva. Amy my mentor. Amy my friend.