In the history of male friendships, there have been a few great and memorable bromances: King David and Jonathan. Alfred Tennyson and Arthur Hallam. Ben Affleck and Matt Damon. This Saturday, a budding musical bromance will reach fruition when local singer-songwriter Steven Fiore takes to the Charleston Music Hall stage backed by new pal and musical admirer Andrew Walker, leader of the shape-shifting Entropy Ensemble.

Fiore, a strummy guitarist with a knack for achy love songs, will be enlisting the help of Walker’s band of musical alchemists for his biggest Charleston show to date. Pianist Walker, cellist Lonnie Root, and an as-yet-unnamed violinist will join Fiore’s usual backing band of drummer Michael McCrea and bassist Mannie Schumpert.

Birthed out of a 2007 orchestral performance of Radiohead songs at the College of Charleston, Entropy Ensemble works exclusively on collaborative projects, from scoring the silent film Charleston, A Love Letter to writing songs to be choreographed at the Charleston Dance Festival. “For Entropy, I’ve always wanted to collaborate with a singer-songwriter, and I was just waiting for the right moment for it to happen,” Walker says.

That magic moment came at the hands of a matchmaker. Eddie White, curator and owner of Awendaw Green, suggested that Fiore play an opening set at a concert of the Ensemble’s Radiohead material at the Hippodrome this spring. Fiore sat in a corner of the lobby at the former IMAX theater, playing through a tiny amp and quickly winning Walker’s admiration. “I remember just being like, ‘Whoa, oh my gosh,'” Walker says. “It was just really honest.”

The Music Hall show will feature more than just bromance, of course. Haley Shaw, a frequent Fiore collaborator, will also lend her crisp, Nashville-worthy vocals to Fiore’s songs. But to see Fiore and Walker sitting on the thinly carpeted mezzanine floor at the Music Hall, each one leaning back and crossing his ankles in a near-perfect mirror image of the other, it’s easy to forget that there’s more to this show than these two guys, locked in a musical embrace.

“I’ve never been more excited about a show in my life,” Fiore says. “This one is a big deal to me.”

In his own right, Fiore (it’s pronounced “fee-OR-ay,” by the way) is a gifted writer with a voice made for heartbreak and confession. On his most recent album, 2011’s words and numbers, on the song “Stay on the Ground,” he sings, “Hey Mr. Teacher / They wrote my name on the bathroom wall / Along with my number / Now all I get is calls looking for a good time.” As funny as the lyric looks on paper, Fiore’s delivery lends a haunted quality and a pathos that make it the most memorable moment on the record. He’s a master of the quirky line that cuts to the quick. Fiore has also been playing a Katy Perry cover at live shows recently, wringing a surprising amount of wistful Americana out of “Teenage Dream.”

Around Charleston, most of Fiore’s shows have been in tight quarters, from dinner shows at Octobachi to house shows and cramped concerts at the Communication Museum. The intimacy of those settings always seemed to fit with the personal nature of his songs, but the upcoming show at the 928-seat Music Hall hints at grander pop ambitions. There’s no telling what Fiore and company will have cooked up by the time the show begins.

“I don’t know any of Steven’s music, and I think that’s honestly an advantage,” Walker says. “I wasn’t a fan of Steven’s because I just wasn’t exposed to any of his music, so now, when I’m learning one of his songs, it’s the first time, so there’s so much freshness.”

Fiore has even enlisted Walker’s help in the songwriting process. In addition to his performance career and a freelance graphic design business, Fiore has a gig selling songs to Universal Music Group. His three successes so far have been a pair of songs for Howie Day and another that got picked up by 2008 American Idol semifinalist Jason Castro — although that wasn’t his original plan. The song, “You Can Always Come Home,” was originally meant for Alison Krauss, but Castro’s label caught wind of it and snatched it up first. “He ended up singing the song, so it’s an interesting compromise,” Fiore says. “But that’s how I got the publishing deal, so I can’t really complain too much.” Fiore still hopes to get the song in Krauss’ hands one day.

Aside from Walker and Fiore, there is one other bromance at the heart of the Music Hall concert. The opening act will be The Prayers and Tears of Arthur Digby Sellers, a project of North Carolina songwriter Perry Wright, whom Pitchfork described in 2005 as “the sort of restrained, concise singer that [Conor] Oberst might one day grow into.” A friend introduced Fiore to the band’s first and only full-length album last year, and Fiore was instantly smitten with Wright’s music. “I’ve never seen him play, but he’s one of my favorite writers,” Fiore says.

“I, being the shameless creep that I am, found him on Facebook,” Fiore says. “I started out the message with, ‘This is going to sound really creepy, but I just love your band, and I needed to Facebook stalk you, find you, and find out what you were doing.'” It turned out the band hadn’t played together in years, but as Fiore and Wright exchanged songs, Wright said he’d be interested in playing a show together.

“He wrote back and was like, ‘I’ve been listening to your stuff,’ and he basically said the words, ‘Your music is inspiring me to play again,'” Fiore recalls. “And I just lost it.”