Listening to Orba Squara’s The Trouble with Flying on a blustery cold London day in October can seem about as pleasant as nursing a summer holiday hangover. Of course, that is in no way an indictment of Squara (aka Mitch Davis), who joins the burgeoning legion of talented one-man shows with all the whimsy of a circus and warmth of spring. But what really gives Squara distinction is the endearing sincerity of his delivery, which belies his dishevelled hirsuteness.

In fact, so unassuming is Squara that it seems churlish to imagine him a troubadour as whack as Ken Kesey or Hunter S. Thompson traversing the heart of America with a wagon full of gnomes to discover the elusive “dream”. But it’s easy to be misled. Squara road-tripped through the country to promote The Trouble with Flying, which includes songs like opener “Treasure Map”, a Moby Dick-like ode to finding “a sunken prize” among every mystical creature and crevasse imaginable. And the title track features a sitar.

But far removed is he from a Tom Wolfe novel; Squara is most disarming when he whispers such lines as: “It’s raining again / But I don’t mind / It’ll give us a chance to get reacquainted”. Perhaps the effect is due to the total unexpectedness of someone who could pass as a hardened hobo summoning such sentiments with a delicate, almost cooing intonation—and be believed.

Gentle life affirmations abound on The Trouble with Flying, their platitudinous quality lining the stomach like cordial thanks to Squara’s authenticity and unassailable musicianship. The album’s title itself suggests that contemporary life is hurtling forward at speeds that prevent us from waking up and smelling the flowers, and other keepers of sanity. Hence Squara’s decision to road-trip through his country like a contemporary Ed Ruscha, taking in every billboard and gas station that one glibly misses travelling by air.

But as Squara explains on his (handsome but not so user-friendly) website, the album’s lyrical matter came as an afterthought to its sonic composition. If there is a theme—which happens to be “searching and finding”—then it is wholly serendipitous. For what we have here chiefly showcases Squara’s precociousness for making something out of “beat up” old instruments including the mandolin, classical guitar, xylophone, sitar, and pump organ. The result is one man’s soundtrack of Americana, harvested from sun-kissed alt-country terrain, that is as distinct as a fingerprint and as universal as the yearning for health and happiness. The voice and guitar tricks of Squara’s childhood rock hero, Billy Squier, feature on the album, most prominently on the title track. 

Equal parts George Harrison, Fleetwood Mac, and Jimi Hendrix, “The Trouble with Flying” is undoubtedly a high point in Squara’s preening of his virtuosity with stringed instruments. “Treasure Map” is a delightfully gleeful, folksy pantomime that anticipates songs like “Very Very (Snow in June)”, unforgettable for its saccharine music box constitution, and “Brand New Day”, a jaunty honky-tonk/ragtime track that could squeeze a tear from even the greatest cynic. But just when you think Squara is headed dangerously down the road of parody—something that would not do for this earnest musician—he springs beautiful no-frills guitar numbers like “Come So Far” on the listener. Coming on the heels of “Treasure Map”, this song has Squara meekly delivering a plea to keep the love he’s found over a lulling nine-string backbone and tender dusting of xylophone. But his plea, winnowing into a near tear-choked whisper toward the end, seems more an aching wish than a newfound reality. The song’s simplistic appeal makes a strong case for Squara’s song-writing talents, a case that is only buttressed by the frontier-finding “Tomorrow” and “New Guitar”, an honest love song to an old guitar.

Given the maudlin fabric of The Trouble with Flying, there’s bound to be a cheesy wrinkle, such as “All the Colors (Picture Perfect)”. With its balmy breeze of chiming guitars, tinkling xylophone, and regulation “ah yeahs”, Squara sullies this carbon copy of a The Boy That’s Least Likely To production with Hallmark lines like, “You go out, the birds all clap their wings / ’Cos you’re a picture perfect painting and you’re awful sweet”. Much worse, though, is “Millionaires”, an infantile tale of Squara’s make-belief about being—you guessed it—a millionaire together with his girl, cabaret-style.

Still, much kudos should be handed to Squara for being brazen enough to pen music that goes straight for the heart, paints hope into a dark horizon, and does so with refreshing anachronism.