19. Travis Tritt
Kentucky born Travis Tritt started out by playing with music in church. He decided to pursue music in high school after receiving compliments from his friends about a song he wrote about heartbreak. Tritt recorded 7 albums for Warner Bros.
His songs charted over 40 times on the Hot Country Songs charts, including five number ones; “Can I Trust You with My Heart”, “Anymore”, “Help Me Hold On”, “Foolish Pride”, and “Best of Intentions”, in addition to 15 more top ten singles.