The Checkerboard Hat Guy: Music by Jerry 'Toledo' Northup
Updated: 7 days ago
"I can see clearly now, the rain is gone ... When I'm with you it doesn't matter where we are ... Here comes Johnny singing oldies, goldies ... Summer breeze makes me feel fine ... How far is Heaven? ... Brother bought a coconut, he bought for a dime ... You know I wish that I had Jessie's girl ... Picking up the pieces of my life without you on my mind, I'm still standing ... yeah, yeah, yeah!"
So it goes as I kick off a show. Great songs and singalongs from the 70's and 80'. There's a few newer and older songs in the mix, too. But all aimed at keeping an upbeat, entertaining and engaging vibe.
"My name's Jerry, everybody say, 'Hi, Jerry!'"
I'm not big on schtick, but mostly people are happy to respond in-kind. It's become a bit of trademark in my shows as a stand-up, solo acoustic guitarist and vocalist. That, of course, and my checkerboard hat.
About 12 years ago, at the Green Iguana in Tampa, I wore it (a gift from my daughter from like ... 1996), people seemed to like it so it stuck. Since March 2024, live performance has been my full-time occupation.
Hundreds of songs played by heart with heart!
My repertoire largely hits the sweet spot between the songs people know by heart and others that ring familiar in the same kind of way. Van Morrison, Chicago, Stevie Ray Vaughn, Clapton, Squeeze, Eagles, Beatles, The Who, Cheap Trick, America, and, of course, Tom Petty, Elvis Presley, Johnny Cash, Jimmy Buffet, Santana … the list goes on. In any given show, I'll also play a touch of jazz, a few instrumentals, blues, and a handful of original tunes that catch the ear ... in a good way!
Live music without a laptop or backing tracks.
What I play comes from more than 44 years of experience behind the instrument. That's a lot. So I've developed a good sense of how to read a room. When to pick it up or slow it down. I see my job as accompanying the conversation in any venue. Not to dominate it. But also to deliver music that's makes an event in itself.
More importantly, my eyes aren’t buried in an iPad, music stand, or cellphone reading chunks of lyrics and chords. I've found those create barriers between myself and the audience. I try to maintain eye contact from the stage outward. I live in Tampa. So, I’ll play anywhere within a couple hours’ drive. Beach bars, restaurants, special events, corporate gigs, dive joints, and any place on the way there or the way back.
Thank you for allowing me in your living room.
I approach every gig with the idea of being a guest in someone's home. I'm courteous and friendly in my stage banter with a measure or two of good humor. In large part, I’ve learned what works and what doesn't. No two gigs are exactly the same, so what I play and when changes with the flow of every show.
My effects rig is a single loop pedal. No cloud-based AI gadgets or vocal harmonizers.
The strumming, the rhythm, the tone, the phrasing, and the touch is 100% me. And that’s a good thing because I always give 100% of what I’ve got to give. I often joke that any mistakes are "human-generated."
With a big tip of my checkerboard hat to booking partners Street Spirit Entertainment and Chandler Entertainment in particular, I've been blessed to have made a go of making "plan B" my "plan A" for earning a living right here in Tampa.
I'd also like to extend my thanks to the following venues for their continued support of me and my music over the years: Bauser's, Indian Rocks Beach VFW 10094, Thomas P's Sports Bar and Patio, VFW Post 2550 Dunedin, Pete's Place South, Walk-On's Sports Bistreaux (Midtown), Whistle Stop Grill & Bar (Safety Harbor), The Niagara Tap, Soggy Bottom Brewing Co., Sandpearl Resort Clearwater Beach (Tate's Island Grill), American Legion Dale Mabry Post 139, Crabby Bill's Palm Harbor, Coconut Charlie's North Reddington Beach, Caddy's Madeira Beach, Cane and Barrel, Bon Appetit Restaurant and Marina Bar, Red Star Live Tampa Bar & Grill, Yuengling Draft House, Beach Birds Beach Bar (Clearwater Beach).
If you're game to take a look and listen, I've got some links for you.
Here's my most recent: Music by Jerry 'Toledo' Northup August 2026.
My most popular has turned out to be this take on the jazz standard "Take Five"
Let's start the conversation! To learn more or discuss potential dates/rates for bookings, I encourage you to text or call me at 567-868-9563 or email to: gnorthup1979@gmail.com.
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