Montgomery Gentry

Montgomery Gentry

Booking Montgomery Gentry

To book Montgomery Gentry or another Country music artist for your private party, corporate event, fundraiser or other function, please fill out our Artist Request Form to quickly connect with one of our Booking Agents.

The staff of Headline Booking Group will work with you to produce a memorable event. Get started now by filling out our no-obligation Artist Request Form and we will work with you to book Montgomery Gentry or another Country music artist for your event.




Montgomery Gentry’s journey into the front ranks of American music has been one of the most gratifying sagas of the past decade. Their road to gold and platinum albums, CMA and ACM awards, a Grammy nomination and highly successful tours has been paved both with musical integrity and with an abiding respect for the people and the genre they represent.


They have released more than 20 charted singles, with anthems like ‘My Town’ and ‘Hell Yeah’ becoming indelible parts of the honky-tonk landscape. They have hit the top of the singles charts five times, with ‘If You Ever Stop Loving Me,’ ‘Something To Be Proud Of’, ‘Lucky Man’, Back When I Knew It All and Roll With Me .

Brothers Eddie and John Michael Montgomery and Troy Gentry joined forces in a band called Young Country until John Michael landed a record deal. His brother joined his band and Troy went solo, winning the national Jim Beam Talent Contest in 1994. 1999’s Tattoos and Scars announced them as a new force in country music, deeply rooted in the blue collar honky-tonk ethos that had sometimes been overlooked in the crossover success of the e90s. By their third album, 2002’s My Town, they had become leaders of a movement that would come to breathe new fire into country music and help bring to the forefront artists like Gretchen Wilson and Big & Rich while drawing from established artists like Hank Jr. and rockers from Lynyrd Skynyrd to Kid Rock.

The hits came with regularity. Eddie and Troy were named the CMA’s Duo of the Year in 2000, and received that year’s American Music Award for Favorite New Artist–Country, the Academy of Country Music Award for Top New Vocal Group or Duo, and the 2000 and 2001 Radio & Records Readers’ Poll award for Top Country Duo.

Their place as honky-tonk ambassadors has long since been established.

Through it all, they remain one with their fans, people who live fully, and work and play for all they’re worth. Their rootedness can be seen in the fact that they are still playing with the band they had in their honky-tonk days. Back When I Knew It All continues their tradition of connectedness as it restates their position as the honky-tonk poets of their generation.

Our Services Include

  • Comprehensive needs assessment
  • Contacting and negotiating with celebrity talent representation
  • O​​ur production staff is available, when necessary to oversee all production elements, ensuring a performance that will exceed expectations.
  • ​Serving as a liaison between your staff and the artist ensuring a flawless performance​

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