late 1980s

Kellie Pickler

A Rocky Start

When Pickler is only two, her mother, Cynthia, flees the alleged physical abuse of her husband, Clyde. Cynthia leaves Pickler with paternal grandparents – Clyde Sr. and Faye Pickler – who raise her. "I've been singing since I was a little girl‚" Pickler says. "My grandma had a collection of children's musical books‚ and we used to sing together all the time." While Pickler's father struggles with alcohol and drug addiction and serves a succession of prison stints, Cynthia is convicted for prescription forgery and charged with writing bad checks.


Kellie Pickler

Custody Tug-of-War

Pickler's mother reappears and is granted legal custody of Pickler. But mother and daughter don't get along. Pickler's grandparents allege in court that Cynthia abused Pickler, although a judge finds her not guilty. Still, Cynthia relinquishes custody, and in 1997, Pickler (pictured with her grandmother Faye) returns to her grandparents. "I'm not as bad as they say," Cynthia tells the Charlotte (NC) Observer. "I just made bad choices."

early 2000s

Kellie Pickler

Eyes on the Prize

During high school, Pickler juggles her role as a varsity cheerleader with her job as a roller-skating waitress at Sonic. At 17, she wins the 2004 Miss Stanly County contest and advances to the Miss Carolina pageant, where she is eliminated. However, as she tells the Memphis' Commercial Appeal, "I really am not a beauty queen. I'm the biggest slob. All I could think about was 'I want to win the talent portion.'"


Kellie Pickler


Pickler Auditions for American Idol

In Greensboro, N.C., the country blonde auditions for the fifth season of American Idol. After three rounds of auditions (all before she met the judges Paula Abdul, Simon Cowell and Randy Jackson), "the American Idol people knew me pretty well," Pickler explains on her website. "So I had nothing to hide about my background. All I had to do was sing. I did 'Since U Been Gone' and then about 20 seconds of 'Broken Wing,' and the next thing you know, I was going to Hollywood!"


Kellie Pickler

January 17

Pick Pickler!

With her loveable babe-in-the-woods persona and powerful country pipes, Pickler cracks Idol's Top 10. But some skeptics feel Pickler's ditzy antics – blundering the pronunciation of "salmon" and admitting she's never heard of calamari – are a shrewdly calculated act. "I never think about what I say before I say it, and that always comes back to bite me in the ass," she tells the Las Vegas Review-Journal. "I don't know how to be anything but myself."

Kellie Pickler

April 26

Goin' Out Big

After making Idol's Top Six with Taylor Hicks, Katharine McPhee and Chris Daughtry, Pickler is eliminated. But less than two weeks later, the plucky singer signs a record deal with Sony BMG Nashville. In September, her first single, "Red High Heels," is released just ahead of her debut album, Small Town Girl. The album debuts at No. 1 on Billboard's Top Country Albums chart.


Kellie Pickler


Pickler Breaks Down

Pickler performs "I Wonder" at the Country Music Association Awards – breaking down in tears toward the end. "This song...has been kind of like therapy for me," Pickler says on Good Morning America. "[Also] I think it's really helped a lot of other people who might be going through similar circumstances." In 2008, her tearjerker performance wins her a CMT Award for Performance of the Year.

Kellie Pickler


Smarter Than Who?

Pickler appears on the quiz show, Are You Smarter Than A 5th Grader, exposing her lack of knowledge that France and Hungary are countries – a gaffe that draws more than 3 million views on YouTube. "It kind of pissed me off that people made such a big deal out of that," she told the Buffalo (NY) News. "Maybe I'm not book-smart, but I'm street-smart." On a sweeter note, Pickler is later nominated for Top New Female Vocalist by the Academy of Country Music, and wins three Country Music Television awards, including Breakthrough Video of the Year for "I Wonder."


Kellie Pickler

September 30

Kellie Goes Two for Two

Pickler, who tops Billboard's Top Country Albums chart with her sophomore album, reveals to PEOPLE that writing songs for her self-titled LP helped her battle a year-long depression. She also opens up about her new love, Nashville songwriter Kyle Jacobs, who wrote two songs with her on her album. "I didn't know someone like Kyle existed," she says. " He makes me feel so good about being me."


Kellie Pickler

June 15

Kyle Picks Pickler!

After more than two years together, Jacobs proposes to Pickler. "It turned out to be the most amazing day of my life," she says of the meticulously planned proposal. "My whole world changed." On New Year's Day, the country singer and her songwriter beau make it official, exchanging vows in an intimate ceremony on a private island in the Caribbean.

Photo Credits

BIOGRAPHY (top to bottom): Courtesy Kellie Pickler; Courtesy Kellie Pickler; Courtesy Kellie Pickler; Ray Mickshaw/WireImage; Ray Mickshaw/FOX; Clark Samuels/Startraks; Rob Hill/FilmMagic; Everett Collection; Joe Buissink

Edited by Julia Wang

Kellie Pickler

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