City Winery Recap - Short & Sweet

May 19th. I finally did the thing I’d been circling for years, the way you circle a plate you’re not sure you should order, knowing full well you’re going to order it anyway.

Some of you have been around long enough to know the truth: before comedy, there was music. Before I learned to make a room laugh, I was dead certain I’d be a rock star. Tequila on private jets. Groupies. The whole stupid, beautiful fantasy. That dream never quite paid out. The jet never landed. But the appetite never died, and appetite, I’ve learned, is the only thing worth trusting.

A few years back, I started dragging my guitar onstage. I’d wanted to for ages, but I kept the two worlds sealed off from each other, like a clean kitchen from a filthy one. I needed to know the stand-up could hold its own first. No prop, no crutch, no six strings to hide behind. Eight years in, I finally trusted it. So I picked up the guitar. Game-changer. One of the kindest things anyone’s ever said to me came after a set: “You were funny, and the guitar didn’t replace the jokes. It lived alongside them. I felt like I got two shows for the price of one.” That one stuck to the ribs.

May 19th, I took it further. A full backing band behind me: drums, a singer, a saxophone wailing somewhere in the dark, bass holding the whole thing down like a good sauce. My entire set, scored. And here’s the part nobody believes: it felt like coming home. No train wrecks, no flop sweat. One quick soundcheck and we walked out and burned the place down. Watching something I’d carried around in my head for years finally take a breath in the real world, that’s the closest I’ve come to seeing the show I dream about when I should be sleeping.

It wasn’t a comedy show. It was an event. Something with a pulse. Comedy and music in the same room is a dangerous, gorgeous combination. Music drags the mood up by the collar. Comedy lightens the unbearable weight of being alive for a few minutes. You walk out feeling like you got away with something.

I can’t wait to do it again.

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What Music Taught Me About Comedy