Ladies love Ray LaMontagne. The singer-songwriter’s striking mix of rugged manliness and bohemian introspection is irresistible. With his virile beard, gruff voice and achingly tender music, he’s like a cross between Manassas-era Stephen Stills and Elliott Smith: macho and hard, yet sensitive and even a wee bit broken as well. These qualities really come out in his lyrics. LaMontagne is a formidable craftsman when it comes to transforming damage and pain into romantic imagery. “Jolene,” from his 2004 debut, Trouble, lays this out perfectly in its opening lines. “Cocaine flame in my bloodstream/ Sold my coat when I hit Spokane,” he growls methodically. “Bought myself a hard pack of cigarettes in the early morning rain.” Brand-new single “Drive-In Movies,” off Supernova, also testifies to this unique skill, especially when he croaks, “I want to be the guy who doesn’t like to fight, who could kick your ass if you touch his girl/ I want to be the guy who breaks all the rules, but the cops let him off because they think he’s cool.” Hell, even bros can fall for a guy that badass.

Musically speaking, LaMontagne is significantly more complex than most singer-songwriters who have achieved a comparable level of popularity. He pens tunes that mass audiences find catchy and appealing, but he is not averse to challenging his fan base. After Trouble made him a pop darling, he returned to the studio and unleashed Till the Sun Turns Black, a slow-motion sojourn into Van Morrison-inspired orchestral rock. God Willin’ & the Creek Don’t Rise represented a similar switcheroo for the artist. The follow-up to 2005’s suave and velvety Gossip in the Grain, the album is at times a crabby slog through ’70s-style folk rock replete with comedown bummer vibes. Hooking up with Black Key Dan Auerbach (easily one of rock ‘n’ roll’s most in-demand producers at this point), LaMontagne has released his most aspiring work to date in the aforementioned Supernova. Fairly reminiscent of Jim James and My Morning Jacket, the record is a dreamy, echo-soaked marriage of rural-fried rock, retro tropicalismo, Southern soul and indie eccentricity. So yeah, LaMontagne is both sexy and ambitious. Our playlist includes selections from each and every one of the singer’s albums. Enjoy. — Justin Farrar