Brandon Stallard and Matt Henley are core members of the Maine blues band Cryin’ Out Loud, a group known for blending traditional blues with Southern rock, soul, and original songwriting. Brandon, a guitarist and vocalist originally from Virginia, built the band through years of performing and drawing inspiration from classic blues and rock artists. Matt, a Maine pianist and keyboardist with jazz and classical roots, brought a new depth to the group through his Hammond organ and dynamic playing style. Together, they’ve helped Cryin’ Out Loud grow into one of Maine’s standout live blues acts, touring throughout the Northeast and building a reputation for energetic, authentic performances.
Brandon Stallard and Matt Henley of the band Cryin’ Out Loud have built their reputation the old-fashioned way — by playing everywhere they can, night after night, and letting the music speak for itself. Their sound blends traditional blues with rock, soul, improvisation, and original songwriting, creating a live show that feels rooted in classic American music while still sounding fresh and modern. Whether performing as a full band or stripped down to a smaller acoustic setup, the chemistry between the two musicians is easy to see.
For Brandon Stallard, music started early. His father was a professional musician, and growing up meant always being surrounded by instruments and working players. As a kid, Brandon remembers top-level musicians constantly coming through the house. His father tried teaching him guitar around the age of eight, but at first it didn’t stick. Brandon learned a couple chords and moved on. Then came Back to the Future. Watching Michael J. Fox’s famous performance in the film changed something. Suddenly he wanted to play for real. He went back to his father and said, “Let’s do this,” and this time the guitar stayed in his hands.
Over time, Brandon fell deeply into blues music. The genre connected with him in a way other music didn’t. He grew up on classic rock from the 1960s and beyond, but once he discovered the blues, it became the center of everything. Eventually, he moved from Virginia to Maine after visiting the state on vacation with his wife. What started as a trip quickly turned permanent. Brandon jokes that even if he lived in Maine for 180 years, he would still never technically be a “Mainer,” but the move completely reshaped his life and music.
Cryin’ Out Loud grew slowly. Brandon spent years cycling through different musicians, searching for the right combination of players before realizing he finally had a true band. He wanted more than technical ability. He wanted chemistry, reliability, and musicians who genuinely pushed each other creatively. Once the right lineup formed, the band quickly gained momentum around Maine and throughout the Northeast.
One major turning point came after the group opened for the Paul Nelson Band at a venue near Sugarloaf. After the show, Grammy-winning guitarist and producer Paul Nelson invited the band to breakfast the next morning. There, after hearing their original songs, Nelson asked if he could produce their debut album. For Brandon and the band, it was a surreal moment. Nelson had spent years working closely with legendary blues guitarist Johnny Winter, and suddenly Cryin’ Out Loud found themselves working with someone they deeply admired.
The resulting album, Play Loud, Smoke Often, helped push the band to another level. Recorded in Bangor and featuring contributions from several notable musicians, the album mixed blues roots with Southern rock and original songwriting influences inspired by groups like The Allman Brothers Band, Little Feat, and The Band. The title itself came from Brandon’s song “I Smoke Cigars and Play the Blues,” inspired by his life after moving to Maine.
Not long after, keyboardist Matt Henley entered the picture.
Matt grew up in Maine and started playing piano when he was just four years old. His grandfather, who played by ear, would sit him on his lap and guide his hands across the keys. The first song Matt learned was “She’ll Be Coming Around the Mountain,” and from there the instrument became part of daily life. As he grew older, he developed strong backgrounds in jazz and classical music while drawing inspiration from artists like Ray Charles, Billy Joel, and keyboardist Reese Wynans.
When Matt joined Cryin’ Out Loud, he was immediately welcomed by Brandon and the rest of the group. Brandon later said he knew Matt was the right fit within seconds of hearing him play. Matt’s keyboard work added a new dimension to the band, especially his Hammond organ playing and ability to move between blues, jazz, and rock influences seamlessly. Though he was the newest and youngest member, Brandon described him as someone who pushed everyone else in the band to raise their level.
Today, Cryin’ Out Loud continues touring throughout the Northeast and beyond, including East Coast runs stretching as far as Florida. The group has become known not only for strong musicianship, but for the camaraderie between band members. Brandon describes life on the road as feeling like “summer camp forever,” full of long drives, jokes, and nights spent making music together.
At the center of it all is a shared love for live performance. Whether playing to packed crowds at the Ivy Manor Inn in Bar Harbor or touring outside Maine, Brandon Stallard and Matt Henley bring a style that feels genuine, soulful, and deeply connected to the traditions that inspired them in the first place.
More From Brandon Stallard and Matt Henley of Cryin’ Out Loud
- https://www.cryinoutloudmusic.com/
- Facebook: @cryinoutloudmaine
- Instagram: @cryinoutloud_blues
- YouTube: https://www.youtube.com/@CryinOutLoud
- Ivy Afternoons: concert series
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Ivy Afternoons logo music of Bar Harbor Every afternoon from May through October, musicians from Mount Desert Island and abroad gather at the Ivy Manor Inn’s garden in Bar Harbor, Maine for good drinks, great music, and some outside goodness.
Ivy Afternoons is a 6 part documentary series.
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