I love Kenny’s Castaways. It’s always been sort of the Bitter End’s neglected little brother, but from the standpoint of actually hearing music, it’s better laid out, and the atmosphere and decor are just classic.
The building dates from the 1820s. Round about 1890, when it was known as The Slide, one of the papers called it “the wickedest place in New York.” Well, in the Giuliani-Bloomberg era there’s not too much wickedness to be had, at least not in touristy areas like Bleecker Street, but you can feel the history when you walk into the bar, musical and otherwise. From Aerosmith to The Smithereens, the list of acts who played at Kenny’s Castaways when just starting out reads like a Who’s Who of rock royalty. Bruce Springsteen’s first NYC gigs with the E Street Band were at Kenny’s.
Seems every time I go in there, whether to play a gig with my band or to catch another act, if it’s early enough I see a lone guitar guy singing folk songs to practically nobody. That’s the 7 PM hour, before the bands show up with their hangers-on, before the tourists wander in, even before most of the regulars who hang out at the bar up front arrive. Well, tonight was my turn to be that guy. 
You can see from my expression that I was having a good time. Didn’t matter that only a few people came (my dad, my aunt, my girlfriend, and a buddy from work, to be exact.)
I felt bad for the duo that played after me – they’d come all the way from Philadelphia and nobody was there to see them (as opposed to me, who might have a thin crowd but gets to walk home.) We couldn’t even hang out to watch them because I hadn’t had dinner, and much as I like to support other musicians, the stomach always wins.
But hey, that’s rock and roll – you gotta play to an empty room sometimes. For a long time, sometimes. Years, sometimes. Till you die, sometimes. The next Whisperado gig is at R Bar the day after Christmas, when we’ll have the whole band and be celebrating our fifth bandiversary. Be there or forever regret it!