Tom Rush is a storyteller by trade Credit: courtesy photo

“I’ve come to realize, by the way, that 2025 is my 65th annual farewell tour.”

This is a joke that singer-songwriter and folk-music legend Tom Rush has been making for years now, but hearing it delivered directly … Orlando Weekly can’t help but cackle like a banshee.

Tom Rush is a storyteller by trade and, well into his 80s, he hasn’t lost a step. He’s got an admirably dry wit and a bottomless well of tales, evidenced by both between-song banter and conversation with Orlando Weekly. (This is the man who, when told he ushered in the age of the singer-songwriter, replied that this was a charge he “was never indicted for.”) And Rush is more musically active than he has been in years, touring and writing new songs at a prolific pace.

“I’ve written more songs in the past 10 years than in the first 50 years,” says Rush. “The songs seem to be popping out, and I think they’re good ones. Of course, if I write a bad one, you’re never going to hear about it. It’ll disappear.”

Orlando gets to experience this particular creative bloom on Friday when Rush plays two shows at Judson’s Live as part of a swing of Florida dates with accompanist and close creative collaborator Matt Nakoa. “I’m lucky to have Matt along for this run,” deadpans Rush, “because he loves to drive.”

Beyond his skills behind the wheel, Nakoa has helped usher in his new creative era for Rush, playing shows together and producing Rush’s latest album, Gardens Old, Flowers New, from 2024 — often knocking out songs in the first or second take. “I think he just got tired of hearing me talk about how maybe someday we’ll make a record,” says Rush. “He booked a studio and hired some fabulous players. Next thing I know, I’m having the time of my life sitting in this studio in Connecticut, and I think it’s my best album yet.”

That’s high praise from a songwriter who penned one of the epochal breakup songs in the popular music canon, 1968’s “No Regrets” — a bleak but clear-eyed lament covered by the likes of the Walker Brothers (“My favorite because it put my first two kids through college”), Ultravox’s Midge Ure and U2.

“A girl came up from New York City, flew up to Boston and spent the weekend with me in Cambridge. I’d never spent that much time with anybody before, and when I took her back to the airport on Monday to fly back to New York, it felt strange walking away alone,” remembers Rush of the song’s genesis. “I went back to my digs and wrote that song, imagining that it was the end of a long relationship, which then actually came to pass. We had this long relationship and it finally ended.”

Beyond his formidable skills as a songwriter, Rush has always possessed an unerring ear for a tune. In the late 1960s, Rush recorded songs by then-unknowns James Taylor, Jackson Browne and Joni Mitchell for his third album The Circle Game (named after his sublime cover of the Mitchell tune) on Elektra. Columbia Records promo copy in the 1970s would duly dub Rush “America’s song-finder.” It’s a quality he still cultivates, most recently in his webcast series “Rockport Sundays,” which sees Rush performing alongside old comrades and, crucially, young performers.

“Some of my guests have been my contemporaries, Jonathan Edwards and Tom Paxton and folks like that. But a lot of them have been youngsters, in some cases, people I’ve never heard of that came recommended. So I said, ‘OK, let’s have them on.’ And they’re brilliant. So yeah, I’m back in the business of trying to expand the audience for young talent.”

For Rush, it’s crucially not about nostalgia but the next thing. “I’ve always been more interested in what’s happening now and what’s going to happen next than what happened before. I’ve had some very fun memories of some wonderful experiences and some not-so-fun experiences, but I’m more focused on now and what are we going to do next. That keeps me engaged.”

And Matt Nakoa is a big part of “what’s next” for Rush musically. The collaboration almost wasn’t, as Nakoa wanted to get a little extra shut-eye (initial response, per Rush: “Tom who? Leave me alone, I want to get some sleep”) when he got the call to show up to rehearsals for a gig Rush was headlining at Symphony Hall in Boston.

“Matt played on one song, and then he played on another song, and then he played on all the songs, because it just sounded so much better with his keyboard parts. At the end of the afternoon, I said, ‘Would you like to do a show with me on the 28th of December?’ And he said, ‘Oh, I don’t know, maybe. What club is it?’ And I said, ‘Well, actually, it’s Symphony Hall.’ And there was a moment of silence, and he allowed as how he could clear his calendar. That’s the first show where we were onstage together. Then a few months after that, I called him and asked him if he’d like to do some more, and we’ve been together ever since, it’s been just over 10 years now.”

On Friday, Rush and Nakoa promise a mix of new songs, old favorites, Nakoa taking the solo spotlight for a few numbers, and even a brand-new ditty. “It’s called ‘It Takes a Whole Lot of Liquor to Like Her.’ People seem to enjoy that one very much.”

Rush has a lot of history in Florida, and he’s happy to escape the lingering New England winter to revisit old stomping grounds. “Early on in my career, I took a year off from Harvard. I was about to flunk out, so I dropped out. I was spending too much time at Cub 47 and I set out to go to California, but ended up in Coconut Grove — geography was never my best subject,” says Rush. “I stayed there for some months, and David Crosby was there and a whole bunch of really talented people. I came in with a whole lot of different guitar techniques and songs and stuff that they’d never experienced before. So I was a sensation for about 20 minutes, until they caught up with it all.”

Florida, it’s time to give Tom Rush another 20 minutes or so.

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This article appears in Feb 26 – Mar 4, 2025.