Hensley made his first public appearance on the Grand Ole Opry at age 11 with Marty Stuart and Earl Scruggs.

His interest in bluegrass guitar developed after hearing Charlie Waller and Jimmy Martin perform at a festival several years later.

Just a few months after Hensley learned to play the guitar (11 years old), he was invited to perform Jimmy Brown the Newsboy on the Grand Ole Opry with Marty Stuart and Earl Scruggs.

Over the years Trey Hensley has performed with and opened shows for many artists such as Charlie Daniels, Steve Wariner, The Oak Ridge Boys, Ricky Skaggs, Blue Highway, J.D.

[7] The album features guest artists including Vince Gill on the Grateful Dead's Brown-Eyed Women, and Taj Mahal on the original title track World Full of Blues.

[10] Bobby Osborne with Sierra Hull, Alison Brown, Rob Ickes, Stuart Duncan, Trey Hensley, Todd Phillips, Kenny Malone, Claire Lynch, and Bryan McDowell (artists), Original (album), Alison Brown (producer), Compass Records (label) Special Consensus featuring Rob Ickes, Trey Hensley, and Alison Brown (artists), Long I Ride (album), Compass Records