At age 20 Toby formed the Easy Money Band and played at local bars while working in the oil industry. At 22 he traveled to Nashville to pass out demos of his recordings, he found no interest in him and he returned home. Luckily for him a flight attendant gave one of his demos to a music producer on one of her flights and the producer saw Keith in concert and went on to sign him with Mercury Records. Toby's career skyrocketed immedietly because "Should've Been a Cowboy" off his first album went number one. In 2005 Toby started his USO tour in Iraq where he performed for the troops. Throughout his career he has released 13 studio albums with 19 number one hits.