Caleb has become a captivating performer, having graced stages across the United States, from Tennessee to California. In summer, 2024, he will return to Nashville to perform at various venues, as well as numerous fairs, festivals, and venues across the Western United States, to share his debut album, "Food Stamps Don’t Buy Flowers," released via Label22 on April 12th, 2024. The album features over ten original songs, all written by Caleb Montgomery himself. The album debuted at #1 on Apple Music Americana charts and #2 on Apple Country. iTunes debuted at #5 country top 100 and iTunes top 50 all genres, an incredible feat for a new, small town artist. Furthermore, he has been nominated for JMA's 2024 male vocalist of the year as well as emerging artist of the year and will be seen on the red carpet at the Grand Ole Opry this October.

Caleb Montgomery is an independent country singer-songwriter. His music is a unique blend of neo-traditional and Western styles, infused with troubadour-style lyrics that are perfect for storytelling. Caleb is one of the newest artists signed to Nashville-based Label22/RCA, Nashville. 

Caleb has a strong fan base across the west with national popularity scores of 40%. (Musicstax, Spotify) Monthly listeners of 22k.