Under the Checkerboard Hat: Music by Jerry 'Toledo' Northup
- Gerald Northup
- Aug 19
- 3 min read
Updated: Aug 26
Let me first say ‘hello’ and thank you right off the bat for taking a moment to read a few words from me about me and what I do in my shows as a solo acoustic guitarist and vocalist. 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 in the 70's and 80's. Van Morrison, Chicago, Stevie Ray Vaughn, Clapton, Buffet, Eagles, Beatles, The Who, Cheap Trick, America, and, of course, Tom Petty, Elvis Presley, Johnny Cash, Jimmy Buffet, Santana … the list goes on and on … but not endlessly.
Live music without the laptop or backing tracks.
What I play comes from more than 44 years of experience behind the instrument. That's a lot. Fortunately, I've found that even for those with the most expansive playlists out there, none of them can play more than one song at a time.
My eyes aren’t buried in an iPad or cellphone reading chunks of lyrics and chords.
With that in mind, I try to make the ones I play count for a bit more. I vary my established sets with older and some newer tunes, along with a few of my own originals that people from every age group in just about every audience can relate to and enjoy among themselves and each other.
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.
No matter where I play, I consider it a privilege.
I work hard to perform songs that fit the place and the people in it.
One guitar, one voice, and a one-pass-loop.
In any given set, I’ll play all the best music I’ve learned how to play.
I don’t download tracks from the cloud or use AI or high-tech gadgets. I’d prefer to leave that work to the DJs. I’m not one and I don’t try to be. I’ve come to believe that for me those tools just put barriers between myself and the audience.
Reading the room (playing songs appropriate for the crowd)
I started playing guitar when I was around 16. From that foundation, 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.
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. Since March of 2024, I've continued to put myself on the line without a net making live music my full-time job.
With a big tip of my 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, Florida.
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).
I like to say that I'm a classically trained marketing copywriter, old enough to have been schooled in the Mad Men form of advertising. Lots of different personalities in that line of work. Almost perfect training to succeed in this line of work as it goes.
Thank you again for reading. 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! Text or call me at 567-868-9563 or email to: gnorthup1979@gmail.com.
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