From down south to Down East: Charley Crockett plays Portland

Who knew there were so many cowboys around coastal Maine?

Well, in truth, I’d had an idea: Saturday night’s State Theater appearance by Charley Crockett, one of the hottest – and most unique – artists in current Country music, had been sold-out many months in advance. I’d secured tickets when they went on sale back in January, and my wife and I then proceeded with plans to host a Portland early-summer weekend built around the show for four of our closest friends, the brothers Zingarini, Paul and Marc, and their respective misseses, Maryellen and Chris, arriving from Pennsylvania and New Jersey, all upwards of 400 miles away. Among other things, the long lead time did give our group of sartorially conscious Northeast attendees ample time to get their all-important Western-wear outfits together.

What it is that makes Charley Crockett so unique is a bit difficult to categorize. I’ll give it a try: he plays modern country music that sounds totally old-fashioned. Or, is it that he takes almost musty, old-west stylings and bestows them with a sophisticated, present-day sheen. Alternately, that his razor-sharp production, instrumentation, and presentation feel like it might suitably be accompanied by a tumbleweed blowing past a swinging saloon door. Maybe those are all somehow about the same thing; Charley’s allure is admittedly hard to pinpoint.

Roughly 24 hours before Crockett was to hit the stage, we began to hit the town. Starting with some malty house-made whiskies at Maine Craft Distilling, as they were prepping to begin their part of Portland’s 2nd annual Feel Good Funk Fest, before moving on to dinner at the casually brilliant Old Port headliner Scales – for both menu and setting, still my favorite restaurant in town after close to ten visits (the breads alone make it worth your while).

Saturday/showday began with a casual stroll along Cape Elizabeth’s serene Crescent Beach, and continued with a midday roof-deck nosh back home facilitated by passes through Washington Ave.’s Cheese Shop of Portland and Commercial Street’s Browne Trading Market (oy, the cost of lobster meat these days!). Then, another exceptional meal, this time at Thistle & Grouse, an outstanding newcomer to Portland’s crowded, elite restaurant scene, where manager Susan, upon learning of the event precipitating our gathering, was nice enough to play some Charley Crockett tunes during the dinner hour.

Finally our highly-expectant group, now supplemented to eight by the surprise arrival from Vermont of Paul and Maryellen’s son “young Marc” and his friend Jane, a SoPo resident (thank goodness no show is truly sold-out in the age of StubHub), arrived at the corner of Congress and High Streets, at Portland’s historic and charmingly vibey State Theater. Double-fisted IPA’s, pilsners, and margaritas in-hand, we staked out our space on the crowded but never uncomfortable GA floor, awaiting the appearance of the new generation country traditionalist who’d brought us all together.

Our sharp-dressed crew about to enter the show

Crockett, who just turned 40, has not necessarily lived the typical cowboy life. Born in San Benito, Texas, tucked in at the southern tip of the Lonestar state mere miles from the Mexican border, he spent formative time in Dallas, New Orleans, New York City, northern California, Paris, and briefly in Spain and Morocco. At 17 Charley bought a guitar at a pawn shop and taught himself how to play. “I started to write songs immediately, without any chord knowledge or anything,” Crockett recounted. “I didn’t know what key I was in for 12 years. But my ear was good.”

His cinematic backstory also included some dark scenes. Coerced into a criminal operation, Crockett evaded potential prosecution when it was determined that his name had been forged onto financial documents…by his brother (that brother, however, was sentenced to seven years in prison for his part dealing in around $40 million worth of securities fraud). Then in 2019 Crockett underwent life-saving open-heart surgery to correct a congenital heart condition whereby two of his three aortic valves had fused together, leaving him with a gnarly scar across his sternum and an ever-present turquoise necklace of a phoenix draped across his chest. “People think my story is far-fetched,” said Charley sometime following that figurative re-birth, “but the thing is I’ve actually toned it down.”

The State show started auspiciously with ‘$10 Cowboy,’ the instantly catchy title-track off Crockett’s just-released new album, his 13th in a prolific recording career still under a decade long. This immediately set into motion a transportive, showman-like, and completely captivating 26-song set list which blended honky-tonk, some soulful R&B, and even blues numbers, along with a few revealing covers (the Waylon Jennings/Willie Nelson combo ‘Good Hearted Woman’ was a particular favorite of our crowd), into the time-traveling Country Western showcase Crockett proved uniquely qualified to deliver.

Charley Crockett, in short, is the real deal. Peering out from beneath his oddly high-perched cowboy hat, his dark, deep-set eyes give you the idea that he’s seen some stuff. With a plaintive, doleful delivery through a clipped Texan drawl, Crockett astutely manages the precarious sonic feat of feeling both retro and contemporary. He has self-described as “sounding like something out of a psychedelic Spaghetti Western.” And he is, as another observer once sensibly put it, “The Cowboy singer for the 21st Century.”

We arose Sunday morning for a two-hour Sail Portland boat charter, breezing past Pumpkin Knob IslandPocahontas Light (as we learned, the smallest lighthouse registered with the U.S. Coast Guard at just 6-feet tall), and the many beautific Casco Bay highlights, while enjoying literal smooth sailing aboard the Eleanor Hawkes led by Captain Kate and first-mate Leah. And our evening, as well as the eventful Crockett-themed weekend, wrapped up with scotch eggs and juicy lamb burgers at pleasantly just-off-the-beaten-path King’s Head Pub.

But in between there was time for a post-show appraisal and to further contemplate an elusive, proper identifier for Charley Crockett’s vintage approach. One thing for certain is that Crockett’s traditional old-west sound is most definitely not a product churned out of the now-dominant, arguably soulless, Nashville pop-country machine. How about one final attempt. After attending the last of Crockett’s recent run of three sold-out shows in London, none other than Jimmy Page – yes, that Jimmy Page – said of him, “I hadn’t seen anything quite like it for a very long time! I was blown away by the depth of his songs, his musicianship and communication with the audience. Charley is a performer in the true cowboy tradition. He’s a troubadour.”

Troubadour. Yeah. I think Jimmy is definitely on to something.

* This post, in only slightly abridged form, also appeared on the Op Ed page of the Portland Press Herald *

Opinion: From down south to Down East; Charley Crockett graces Maine


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