If at first you don’t succeed, try, try again (with a cowboy hat on).

Conway Twitty

In the mid-‘50s, every record label wanted their own Elvis Presley. MGM hired Harold Jenkins, a singer-songwriter from Mississippi just home from fighting in the Korean War. Thinking his real name was boring, he renamed himself “Conway Twitty” (after towns in Arkansas and Texas, respectively). MGM released several Elvis-esque Twitty rockabilly singles, but none were hits. Then in 1958, an Ohio DJ played a B-side of one of those, a country song Twitty wrote called “It’s Only Make Believe.” It went to #1. Within a few years, Twitty had gone country full time. By the time of his death in 1993, Twitty amassed 75 top 10 hits on the country chart, including 40 #1 hits.

Jessica Simpson

Like Christina Aguilera and Britney Spears, Simpson rode the wave of blonde-teen-pop stars to fame in the late 1990s. She’s probably better known for her reality show, Newlyweds, because she scored just one top hit 10 (“I Wanna Love You Forever.”) In 2008, she made a country single called “Come on Over,” which hit. A full country album called Do You Know debuted at #1.

Darius Rucker

Hootie and Blowfish sold a staggering 16 million copies of their debut album Cracked Rear View in the mid-‘90s. They won a Grammy for Best New Artist, but album sales dropped off substantially ever since. Lead singer Darius Rucker took a stab at R&B in 2002 to little attention, and so the South Carolina native signed with Capitol Nashville.

Learn to Live came out and Rucker became a star again. The first three singles from the album all hit #1 on the country chart. Only three other country stars had had their first three singles reach the top: Clint Black, Wynona, and Brooks & Dunn.