Uncle B’s Damned Ole Opry Plays and Sings The Greatest Christmas Show Ever!

Uncle B’s Damned Ole Opry is Bryan Simpson’s irreverent trippy-trad tent revival of a musical experience currently in residence in the Neon Steeple at Chief’s on Broadway in Nashville. It’s Billy Strings meets Barnum & Bailey, He-Haw meets Half-Baked. In short, a serious musical circus. Uncle B assembles an A-List of Nashville’s finest talent (past guests have included  Charlie Worsham, Dan Tyminski, Sierra Hull, Madeline Edwards, Trey Hensley, Caitlyn Smith, The Band Loula, Ashley Monroe, Jason Carter, Suzanne Cox, Ashley Gorley, Sarah Buxton, Brit Taylor, Sam Williams, among many others), and each month Uncle B and his guests tackle a new music assignment.

Website

 Madeline Edwards

Madeline Edwards makes music for the deep feelers—the ones who’ve known loss but still choose love.

Raised in Houston after moving from California in grade school, she’s the oldest of five and grew up fast in a broken home. By 14, she was gigging in bars and eventually put herself through college at the University of Houston, studying advertising and law—while picking up side hustles (including walking dogs) to help support her family.

After over a decade of writing, producing, and performing independently, a Tiny Desk performance with Tobe Nwigwe changed everything. A few DMs and one roommate-wingman later, she met her now-husband Jim. They got married and moved to Nashville to give music everything she had.

In just two years, she signed with Sony Music Publishing and Warner Music Nashville, sang with The Highwomen on a Lady Gaga track, opened for Chris Stapleton and Willie Nelson, made her Grand Ole Opry debut, and performed at the CMA and CMT Awards.

Then, everything shifted. Edwards lost her brother to suicide after his battle with schizophrenia. Months later, she was dropped by her label, management, and most of her team.

What followed was FRUIT—a record born from grief but rooted in hope. A revolution: her music doesn’t just transcend genre, it transcends generations. With FRUIT, she’s ignited a quiet movement of people healing through story, spirituality, and song. In 2025, she joined Willie Nelson and Bob Dylan on the Outlaw Tour.

Cadillac Sky

Nashville-by-way-of-Texas-based bluegrass quintet Cadillac Sky are led by singer/mandolin player/guitarist/violinist Bryan Simpson and feature Matt Menefee (banjo, upright piano, drums, glockenspiel), David Mayfield (guitar, percussion), Ross Holmes (mandolin, Mellotron), and Andy “Panda” Moritz (piano, percussion, bass). The group signed to the Skaggs Family label and released its debut album, Blind Man Walking, widely considered to be one of the greatest albums in Progressive Bluegrass music. Gravity’s Our Enemy followed in 2008, and Cadillac Sky switched to Dualtone Records for Letters in the Deep, produced by Dan Auerbach of the Black Keys.

After a 17 year hiatus, Cadillac Sky has reunited to celebrate the 20th anniversary of their debut album.

Jehry Robinson

Jehry Robinson is an American genre-blending rapper, singer-songwriter, and producer from Long Island, New York. Known for creating a “genre-less” sound, he weaves together a sonic tapestry of hip-hop, reggae, alternative rock, and pop. He is currently signed to Tech N9ne’s independent powerhouse label, Strange His debut project under the label, 20/Twenty – Chapter 1, quickly validated the signing by peaking at #23 on the Billboard Rap chart. He followed this momentum with major full-length studio albums, including 20/Twenty (2020), Hella Highwater, and Drink More Water (2023). His prominent tracks often feature collaborations with label boss Tech N9ne and heavy hitting lyricists like Rittz. Known as a highly personable performer, Robinson has toured heavily, including opening on Jelly Roll’s Son of a Sinner tour in 2022 and subsequently launching his own successful headlining tours.

Mother/Son

Mother-Son (Suzanne Cox & Brandon Ratcliff)  have become viral sensations with their heartfelt renditions of favorite hymns. Suzanne Cox is  a member of The Cox Family. They can be heard on the O Brother, Where Art Thou? soundtrack, and their 1994 collaboration with Alison Krauss which won the 1995 Grammy Award for Best Southern, Country or Bluegrass Gospel Album. In recent years, the band has celebrated many opportunities starting with debuting their latest single on the Dailey and Vincent Show and performing to a sold-out crowd at Nashville’s famed Station Inn.  Brandon Ratcliff burst onto the scene in 2019 with his debut single “Rules of Breaking Up.” After a year of highlights including opening for Kelsea Ballerini, Brett Young, and Keith Urban, being selected as a Pandora Ones to Watch artist, and topping Rolling Stone’s all-genre Breakthrough Artists Chart, the world came to a screeching halt in 2020. At a crossroads with his music, and his life, Ratcliff went back home to figure out who he was and what he wanted to say, and write his next project. Greatly influenced by the music of the Louisiana delta and the bluegrass engrained in his blood from his Grammy Award winning mother, Suzanne Cox of the legendary bluegrass group The Cox Family, Tale of Two Towns is a coming-of-age record that reads like a book of Ratcliff’s life these last few years.

Colin Nash

Born & Raised in the little town of Salem, Missouri, Collin Nash grew up surrounded & consumed by music. The sounds of George Jones, Roger Miller, Tom T. Hall and Merle Haggard taught him how to tell stories. For nearly a decade, he has written & been a hired gun for many country music artists. He has co-written songs for Tyler Halverson, Ben Chapman, Harper O’Neill as well as many others. Now stepping out on his own with a blend of raw country, americana & bluegrass, Collin brings forward a fresh, yet familiar approach to the craft of songwriting & storytelling.

Corduroy Cadets

Corduroy Cadets are a Nashville-based band blending elements of folk, bluegrass, and country into a rich, harmony-driven sound. Known for their tight vocal harmonies and inventive arrangements, the band reimagines beloved classics while showcasing compelling original songs that highlight their musicianship and storytelling. Each member of Corduroy Cadets is a multi-instrumentalist, singer, and artist in their own right, creating a dynamic and versatile live performance. From driving bluegrass rhythms to heartfelt folk ballads and high-energy country favorites, their shows move seamlessly between intimate and electrifying moments.