Frederick Dierks Bentley was born in Phoenix, Arizona, on November 20, 1975, to Leon Fife Bentley, a bank vice president, and Catherine Childs. Dierks' biggest hits include “What Was I Thinkin'” and “Drunk on a Plane”.

Dierks married Cassidy Black on December 17, 2005, in Mexico. They, who would also become an inspiration for one of his albums. The couple have three children, including their firstborn Evelyn Day “Evie” Bentley, who provided additional vocals at the end of “Thinking About You.”

Other than music, the singer-songwriter has his pilot’s license and owns a Cirrus SR22. On top of that, Dierks has his own country bar, Dierks Bentley’s Whiskey Row. The bar has opened in 4 locations: Nashville, TN; Denver, CO; Gilbert, AZ; and Scottsdale, AZ. The Nashville branch has been the location for the Whiskey Jam event since September 2023.