in 1983 when he became lead vocalist of the Tennessee River Boys, a group that performed at the Opryland USA theme park in Nashville. This band was originally intended to perform a one-time show to promote the park, but became one of several regular performers there. Herndon left the band after only a year to become a contestant on the television talent show Star Search. Following Herndon's departure, the Tennessee River Boys underwent a number of membership changes and became Diamond Rio. When his tenure on Star Search proved commercially unsuccessful, Herndon attempted to secure a recording contract in Nashville. He told The Tennessean in 1995 that multiple labels rejected him as they considered him a "pretty boy". Despite this, he found work singing jingles for Pepsi and Dodge, as well as demo tracks for other artists. He lost a significant amount of money due to an unfavorable management deal, which led to his mother having to sell her house in order to refinance the amount of money lost. In addition, Herndon's father died of a brain hemorrhage, putting further strain on both him and his family. Herndon then moved to Texas and found work performing in various honky-tonks across the state, in order to regain some of the money he had lost. His tenure in Texas included a stint with Louise Mandrell in 1987 at Billy Bob's Texas, a country music nightclub in Fort Worth. He competed on another television talent show titled You Write the Songs in 1987, but was unsuccessful. Herndon also appeared on The Porter Wagoner Show, a musical variety show hosted by country singer Porter Wagoner. By 1989 he had formed a backing band called Bayou. This act opened for Little Texas in 1989 prior to that band's signing with Warner Records. In 1993, Herndon won a local music award called Texas Entertainer of the Year. At the awards ceremony, Herndon was discovered by a representative of Epic Records, and he signed with the label later in the year. Career 1995–96: What Mattered Most Herndon began recording music for Epic in 1994. He made his debut in early 1995 with the single "What Mattered Most", a song written by Gary Burr and Vince Melamed. The song went to number one on the Billboard Hot Country Songs charts in the United States and the former RPM country music charts in Canada. Follow-up single "I Want My