Checkpoint Charlie’s, New Orleans LA

I have only been to New Orleans once before, on tour in 2010,but I immediately fell in love with it then. I felt like there was something undefinable, that goes beyond the gingerbread on the shotgun shacks and the brass bands and the po’boys, which gave it a feel like no other American city.


That feeling greeted me again when I disembarked from the Megabus, after a 5-hour trip from Houston. I decided to walk the mile and a half to my hotel, through the French Quarter and into the Marigny, just to enjoy it. I wasn’t even bothered by all the tourists (a group to which I belong, of course, more or less), with their plastic margarita glasses and bags of Cafe du Monde memorabilia. The city just exudes a welcoming, mysterious charm.


I met up with some friends from Arkansas who were spending a few days in the city, and had a beer at Lafitte’s, the oldest bar in the USA. It certainly looks it, from the age of the building and the bar itself, though the whirling frozen daquiri machines behind the bartenders showed how it had been upgraded to meet contemporary demands on Bourbon St.


I had an interview to do, so I returned to the hotel and connected with the journalist. It was a very in-depth conversation, with lots of questions about my various musical experiences before arriving on my current M.O., and was a lot of fun, though it went on for over 30 minutes and I began to wonder what kind of article she’d be turning out. (I hate to report that, as of this writing, I still haven’t seen any sign of the interview, which was to help promote the next night’s gig).

Then it was time to pull on my new boots, grab the guitar and head to the gig. I’d never been to Checkpoint Charlie’s before, and upon entering its prime corner location on Esplanade, found a yawning space with several levels and a good-size stage far in the corner. I plugged into their PA, noting the various signs declaring “$5 charge to use the PA – no charge if you don’t make $5”, which seemed pretty kind-hearted of them.

I was expected to provide 3 1/2 hours of music this evening, and I had resolved to not repeat anything, and to depend on originals as much as I possibly could. This meant bringing out a lot of tunes I wouldn’t normally play in a bar, like mellow fingerpicking pieces I’d written for weddings, but it seemed like a good challenge to mix them in.

When I hit the stage at 7 p.m., there were just a few people sitting at the bar, and a few in a raised area with billiard tables, none of them paying any attention. This is a tough situation; I didn’t want to waste my best songs on them, but I also wanted to try to grab their attention if I could. And at the same time, I wanted to make it seem like I was in control of the situation, so if someone walked in the door they’d be drawn in, not put off by the whiff of desperation. (Of course, I should be thinking about the music and the music alone, but these are some of the things that go through the head of a performer).

I decided to start out quiet, but confident, with some of the fingerpicking tunes, then tried out one of the few covers I’d planned to include, Dylan’s “Just Like a Woman”. That, finally, elicited some glances and a burst of applause at the end. I ramped up the energy a bit and continued on, happy to see that some of the glances turned into actual listening, and before long a few other people came through the door to join them.

I finished up the first set, took a short break, then went back on. More people showed up, replacing others who’d left, and I pushed on through my back catalog. I got some nice compliments on the next break, and some CD sales, and during the third set there were folks sitting in front of me for the sole purpose of listening and watching. I played four Beatles songs, and “Shenandoah”, but otherwise stuck to my own tunes, and by the time I was done my fingers were aching but I was happy with the way things had turned out. I rewarded myself with straight bourbon and some brass band action up the street at DBA, then an oyster po’boy after midnight with my friends. A great night.