Theo and Brenna MacMillan are originally from Winchester, Kentucky where they grew up with ten other siblings. A variety of creative talents among all of the siblings were recognized, encouraged and supported in their childhood home. Theo and Brenna assembled the Theo & Brenna Band in 2018, cut their first record (When You Go), and spent 2019 playing shows throughout the Southeast.
Growing up, Brenna sang harmony parts in bluegrass bands, children's choirs, church choirs, and family gatherings. She began to play the banjo when she was nine. Throughout highschool, she dabbled in various genres of music, performing anything from R&B hits to gospel numbers. Through adoption, the family changed dramatically in size and lifestyle when she was eleven, and at this time her love for the rhythm of a banjo roll developed from researching the banjo in West Africa and listening to Liberian drumming. In college, she joined Theo in the college bluegrass band, an experience that solidified a latent love for playing bluegrass music. Brenna toured with the Berea College Bluegrass Ensemble in the United States and Europe, and was the recipient of the Red Foley Memorial Music Award in 2018. She completed her Bachelor's Degree in Chemistry and then moved to Nashville in May of 2018.
Brenna is often praised for her exciting banjo playing and gentle soprano singing. Her vocal abilities are highlighted by tonal purity. She loves traditional roots music, classic country, waltzes, and sad songs; she creates her own songs out of personal stories and writes regularly.
From a young age Theo had an intense interest in music. Performing in local choirs, churches, family concerts and talent shows kept him on the stage. He started playing piano at five years old and fiddle at seven. His interests in writing grew when he picked up guitar at eleven. Theo was introduced to bluegrass when Brenna was given a banjo that same year. Theo continued to write throughout high school and began to make plans to move to Music City after a visit to Nashville in 2010.
While attending Berea College, Theo was connected with Al White, the director of the Bluegrass Music Ensemble at Berea College (previously of the Bluegrass Alliance, McClain Family Band). Theo played with the Bluegrass Ensemble for three years, singing lead, harmonies and playing fiddle. His senior year Theo was given the Red Foley Memorial Music Award by Berea College for his role in the Bluegrass Ensemble and his active involvement promoting roots music on campus. Theo works as a software engineer in addition to playing with the Theo & Brenna Band.
Theo writes and co-writes regularly, supplying the band with new material to supplement other originals, traditional songs, and covers.
Building on two years of participating in the Berea College Bluegrass Ensemble together, Theo and Brenna began scheming up plans to continue playing music after graduation. 2016 saw Theo move to Nashville where he continued writing and producing music. He also began playing occasional gigs as a side-man and fronting local shows to work out new material. Meanwhile, Brenna continued to play a prominent part in the college group. After she made the post-grad move to Nashville in 2018, the siblings began booking local shows and recruiting their band.
Theo & Brenna Band has had the honor of including such talents as Mary Meyer, Maddie Denton, and Evan Winsor, among others. Both siblings are avid songwriters; live shows prominently feature original material from the sibling duo, along with re-imagined classics from the likes of Glen Campbell, Emmylou Harris, Paul Simon, and Willie Nelson. The shows also incorporate traditional bluegrass standards from groups like the Osborne Brothers, Stanley Brothers, and Bill Monroe.