In 1999, Shania Twain was at the peak of her commercial success. Two years prior, she had released the blockbuster country album Come on Over, a record that would sell a staggering 40 million copies worldwide (by comparison, Taylor Swift's best-selling release so far, Fearless, has tallied a little less than 9 million). Featuring hits like "Man! I Feel Like a Woman," "You're Still the One" and "That Don't Impress Me Much," Come on Over became a genre-busting sensation, due in part to a re-released pop mix of the album. An accompanying tour further solidified her as country's most recognizable female superstar.
Still, Twain didn't garner her first — and only — Entertainer of the Year nomination until 1999, competing against Tim McGraw, George Strait, the Dixie Chicks and Garth Brooks, who was angling to three-peat in the category. But when Reba McEntire, the last woman to win the CMA's top award in 1986, was chosen to present, Twain had to feel the odds were on her side.
Which, of course, they were. McEntire, visibly emotional over Twain having ended the 13-year drought of female Entertainer winners, pointed in her direction and informally beckoned the Canadian native to the stage. "Come on up, Shania Twain," she said.
"I'm embarrassed that I'm crying," Twain said during her speech, wiping away tears. She also offered a good-natured directive to Dolly Parton, who was inducted that evening into the Country Music Hall of Fame. "I have to meet Dolly Parton tonight after the show. She is my biggest inspiration of all time and she can't leave the building until I at least meet her!"
Twain went on to follow up Come on Over with 2002's Up! and a greatest hits compilation in 2004, before slowly dropping out of the public eye. She endured a divorce from her producer husband Robert "Mutt" Lange and subsequent vocal issues, before making a high-profile — and triumphant — return to the stage in 2012, headlining her own Las Vegas spectacle, Shania: Still the One. A regular showroom draw at Caesars Palace's Colosseum, the show is currently scheduled to run through summer 2014.
Remarkably, despite all her success, sales and stardom, Twain's 1999 Entertainer victory stands as her sole CMA Awards win.