Jon Cleary’s musical heart was already in New Orleans while he was growing up in the English town of Cranbrook, Kent (population: 6,000), where he happily attended nearby shows by The Clash, The Damned, The Adverts and other upstart young English punk-rock bands in the second half of the 1970s.
“Most of the pop music then was dreadful!” said Cleary, who moved to New Orleans in 1980 at the age of 18 and won his first Grammy Award in 2016. He and his Big Easy-based band, The Absolute Monster Gentlemen, will headline the 2026 edition of San Diego’s four-day Gator by the Bay festival next weekend. They will return in the fall as the opening act for Bonnie Raitt’s concert at The Rady Shell at Jacobs Park.
Cleary was a member of Raitt’s band for more than a decade, starting in 1999. His many recording credits also include work on albums by such varied artists as B.B. King, former Ocean Beach resident Rickie Lee Jones, India.Arie, John Scofield, Taj Mahal, Jimmy Smith, Ryan Adams, Eric Burdon, D’Angelo and such past and present Louisiana music greats as Irma Thomas, Dr. John, Walter “Wolfman” Washington, Charmaine Neville, Johnny Adams, Rockin’ Dopsie Jr., Bobby Charles and Marva Wright.
That makes him ideally suited to be one of the headliners at Gator, which takes place at Spanish Landing Park, trucks in 10,000 pounds of crawfish from Louisiana and bills itself as “Mardi Gras by the Bay.” This year’s four-day edition will feature more than 100 performances on seven stages by a lineup that also includes 2011 Grammy Award-winner Chubby Carrier; Geno Delafose & French Rockin’ Boogie; The Pine Leaf Boys, featuring Wilson Savoy, and many more.
“I get hired to do recording sessions and perform with other artists because the New Orleans piano tradition is my default, my natural way of playing music,” said Cleary, who in a 2006 San Diego Union-Tribune interview memorably noted: “I speak with an English accent, but I only play music with a New Orleans accent.”
The tradition Cleary is immersed in is a zesty stylistic gumbo that incorporates elements of ragtime, stride, gospel, boogie-woogie, rhythm-and-blues, rhumba, mambo, jazz, gospel, blues, rock ‘n’ roll, funk and the rollicking second-line parade marches that were born in New Orleans in the late 1800s.
It’s a tradition that he first embraced as a kid. His family included several generations of musicians.
“I had the same influences all my friends at school did, from just being where I was at the time,” said Cleary, whose hometown is not quite midway between London and Dover.
“And then I had all this extra stuff from my family members, the grown-ups in my family, who all were passionate about music. So, I got a pretty good education and feel for, essentially Black American music, with a lot of other incidental stuff, like traditional Irish music. My mum was part of the generation of English teenagers who — in the post-World War II years — embraced the sound of New Orleans jazz as a new thing for them.
“People cherished rare 78 RPM records they would pass around amongst their friends, and that’s a passion my mother still has. I grew up going with her and my dad to see the local guys that played New Orleans jazz in England, where almost every village had a New Orleans Dixieland band.”
English-born musician Jon Cleary kicks back in New Orleans, his adopted hometown since 1980. (Courtesy Gator by the Bay)
Cleary started off on guitar when he was 5. He turned to piano after experiencing a key epiphany in 1974 when he was 11. One of his uncles, who had lived in New Orleans for several years, paid a visit to Cranbrook, Kent, bearing “lots of great stories and lots of great records.”
Most of those records were by pioneering pianist/singers who were largely unknown in England at the time, most notably Professor Longhair, Fats Domino, Allen Toussaint, James Booker, Huey Smith and Dr. John.
Cleary was further intrigued when he discovered that two of his favorite records released in 1974 — Frankie Miller’s version of “Brickyard Blues” and Robert Palmer’s version of “Sneakin’ Sally Through the Alley” — were both written and produced by Toussaint. He was similarly captivated by Longhair’s early 1965 single, “Big Chief,” which to this day is a mainstay in the repertoire of many New Orleans-based performers, Cleary included.
“All of those guys changed my life,” he said. “They were very inspirational to me.”
So inspirational that, as soon as he graduated from high school, Cleary moved to New Orleans to immerse himself in the city’s rich musical and cultural melting pot. He had to move back to England twice after his visa expired but returned to New Orleans as soon as he could each time.
When Cleary married former New York costumer Trish Gorman in 2005, Professor Longhair’s son, the Reverend Byrd, performed the service. It was held on the balcony of the couple’s home in the New Orleans neighborhood of Bywater, which inspired the title of Cleary’s latest album, the frequently galvanizing “The Bywater Sessions.”
Cleary spoke with the Union-Tribune recently from that same home, which houses his recording studio. The interview has been edited for clarity and length.
Jon Cleary will headline San Diego’s 2026 Gator by the Bay festival, then return to San Diego in the fall as the opening act for Bonnie Raitt’s concert at The Shell. (Courtesy Gator by the Bay)
Q: The legacy of New Orleans piano extends from Jelly Roll Morton through Professor Longhair, Huey ‘Piano’ Smith, James Booker, Ellis Marsalis and beyond. You’re obviously not a native of New Orleans, but I’m wondering how you see yourself — after 40-plus years living there — fitting into this legacy of New Orleans piano?
Cleary: I suppose, ultimately, that’s something for other people to assess — in retrospect. I just do the job. I do feel I have a certain privilege. Having been born in England and having spent the first 18 years of my life there, I’m blessed to have two cultures and a foot on either side of the pond. Perhaps that means I appreciate all this music more, because it’s never ceased to be remarkable to me.
The irony is, if I’d been born in New Orleans, I’d probably be listening to English rock music or something! But part of human nature that it’s “the other” that always seems more exotic, and that’s never ceased to be the case for me. I’m incredibly in awe of New Orleans musicians, New Orleans culture, the people in the city and everything about it. I’m also privileged in that I can have a take on all of it that comes from the inside and the outside at the same time.
Q: You started off as a guitarist. What was the allure of the piano over guitar for you?
Cleary: When I came to New Orleans, I didn’t bring a guitar with me and the house that I moved into had a piano. And it was piano that was getting my attention. It has such a wide range, and it’s such a great percussion instrument, that playing it is like suddenly bursting into a great big field. You’ve got so much room to romp in that going back to guitar always felt like a diminishing process.
Q: You moved to New Orleans when you were 18 and almost instantly got a job as a handyman at the Maple Leaf — one of the city’s great live-music bars — where James Booker lived and often performed. How pivotal was that?
Cleary: I was very lucky to get to see Booker a great deal. I had access to all this great information. As a kid, I was precocious and hungry for musical information, so I voraciously consumed as much as I could. So, by time I got to New Orleans, I was ready to take a deep dive.
Q: How did you come to work at the Maple Leaf?
Cleary: The owner gave me a job painting the joint. I’d be in there every day, painting and Booker used to stay upstairs. He had a little room at the back of the bar because he was being managed by one of the Maple Leaf’s co-owners. So, he would hang out there because he got free drinks. Quite often, in the daytime, it’d be me on a ladder painting and James Booker playing away at the piano.
Today, a lot of people have heard about James Booker and you can see his videos on YouTube. But back then, Booker couldn’t get arrested. Well, he could get arrested, but almost no one knew he was. He had a Tuesday night residency at the Maple Leaf and there’d be, like, 18 people there. Booker would play this amazing stuff. And it seemed bizarre that there was this gorgeous music going on and the joint would be empty. But that was what New Orleans was like at the time.
Q: Harry Connick, Jr. told me that when he was a kid, he took piano lessons from Booker. Did you, formally or informally, also take lessons from Booker?
Cleary: No, I never did. But I had so much exposure to him that that’s how I learned. I’ve never been very good at taking lessons. I prefer to ingest the music through osmosis and let it all soak in. I think that way you develop your own style a bit better. With hindsight, I probably should have been a lot smarter and asked Booker for lessons. But I didn’t have any money to pay him for lessons. And I don’t think he would have been interested in giving lessons. I think a big reason he gave Harry lessons is because Harry’s dad was the district attorney of New Orleans.
Jon Cleary accepts the Grammy award for Best Regional Roots Music Album for “Go Go Juice” at the 58th annual Grammy Awards in 2016, in Los Angeles. (Matt Sayles/Invision/AP)
Q: Your story could be a screenplay. A teenager from England moves to New Orleans, doesn’t know anyone there, and before too long is playing gigs as a pianist with Snooks Eaglin, Ernie K-Doe and other New Orleans music giants, before launching his own solo career. It almost seems like a script for a movie called “Pinch Me. I Must Be Dreaming!” Did it feel that way to you?
Cleary: Well, it did, but it wasn’t sudden at all. It took a long time! Basically, I lived here in New Orleans for two years, just listening, and then going home every night and sitting at the piano playing for hours, trying to remember what I’d heard and figuring it out. It was like all my friends had gone to universities to study for two years, and I was in New Orleans, and it was like my university.
But I didn’t really hustle any gigs until I felt I was ready. I’ve got so much respect for the music, and I had so much respect for the musicians, I never would have dreamt of trying play with them if I didn’t know what the job was and how to do it. So, I spent two years and didn’t really play any gigs with anybody. I just listened and worked. And then I had to leave the country because of my visa. I went back to England, where I got a gig with my uncle, and started working as a professional musician in London on the pub scene. I did that for about a year and a half.
Q: What kind of music were you and your uncle playing?
Cleary: I was playing straight-ahead New Orleans R&B and using musicians that I met in London. It was a big deal being in London, and there was a good pub circuit. That’s where I really learned the trade, the business aspects of how to book a gig, how to get it listed in the magazines, how to hustle hiring musicians, plugging in a sound system, figuring out how much I could get made from ticket sales, and paying everybody at the end of the night.
It was sort of amateurish, but that’s a great way up, a great entre, and I learned a lot of nuts and bolts. I went back to New Orleans and then I felt right. I had the music under my belt, and I understood the business a little bit. That’s when I started hustling in New Orleans and when I got Professor Longhair’s old Monday night gig at Tipitina’s and James Booker’s old gig on Tuesday nights at Maple Leaf because he had died in the period while I was away in England.
I did some touring with John Mooney and then started playing in the rhythm section for Snooks Eaglin. Through that, I met Ernie K-Doe, Jesse Hill and Tommy Ridgely, and then I was working every night in New Orleans with them and then doing solo gigs, playing my own stuff.
Q: In hindsight, was there a major turning point for you?
Cleary: I remember the first night I got to play with Earl King on stage at Tipitina’s. I thought: “This is what I’ve been working for towards for years and years and years, since I was about 12 years old and first heard Earl King’s records in my uncle’s house in England. And now, I’m on stage with him at Tipitina’s, and he’s digging it!” I could tell he was digging having me on the piano because I knew the solos to his old tunes. That was a major rung of a long ladder that I’d managed to get to. I knew I still had a long, long way to go, but that felt really good.
Q: How old were you?
Cleary: I was 23. My first gig with Johnny Adams was also very special and I later got to perform with him in Tokyo. I am so lucky to have been shown so much kindness by all the music community here in New Orleans. I think a lot of the old cats were delighted to find a young person coming up that was so interested in in their music. And they were genuinely pleased I knew how to play their stuff, which was very encouraging to me. I’ve been so blessed in my career and have had so many magical moments.
The 23rd annual Gator by the Bay
Featuring: Jon Cleary & The Absolute Monster Gentlemen, Dumpstaphunk, Chubby Carrier & The Bayou Swamp Band, Geno Delafose & French Rockin’ Boogie, Pine Leaf Boys, Rick Estrin & The Nightcats, John Németh with the Johnny Vernazza Band, Deke Dickerson, Mitch Polzak
When: 5 to 9 p.m. Thursday, May 7; 4 to 10 p.m. Friday, May 8; 11 a.m. to 10 p.m. Saturday, May 9; and 11 a.m. to 7 p.m. Sunday, May 10
Where: Thursday at Sheraton San Diego Resort’s Lanai Lawn, 1380 Harbor Island Drive, Harbor Island; Friday through Sunday at Spanish Landing Park, 3900 North Harbor Drive, across from San Diego International Airport
Tickets: Children 17 and under are admitted free with a paying adult all weekend. The Thursday night event at the Sheraton is free. Single-day GA tickets on Friday, Saturday and Sunday are $80-90. Three-day GA weekend passes are $230. Single-day VIP tickets are $200-$250. Three-day VIP passes are $625. Discounted tickets are available for active-duty military members with ID.
Online: gatorbythebay.com
