Kellie Pickler; Photo via ABC, American Idol
Pickler’s appearance came during a special 20th High School Reunion-themed episode, which brought back several contestants from the Class of 2006, including Pickler, Bucky Covington, Taylor Hicks, Paris Bennett, and Elliott Yamin.
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The moment carried extra meaning as Pickler joined Harper for a performance of “A Broken Wing,” the same Martina McBride song she sang during her American Idol audition two decades ago at just 19 years old.
Pickler went on to advance in the competition, winning over viewers with her sweet Southern charm and ultimately placing sixth. She released her debut album, Small Town Girl, later that year on October 31, 2006. The project was anchored by her breakout single “Red High Heels” and also featured fan favorites like “Things That Never Cross a Man’s Mind” and the deeply personal “I Wonder,” which reflected on her tumultuous childhood and her absent relationship with her mother.
She also scored a major success with her Platinum-certified single, “Best Days of Your Life,” from her self-titled sophomore album. Later, she released two additional albums 100 Proof (2012) and The Woman I Am (2013).
In May 2013, Pickler and her partner Derek Hough took home the Mirrorball Trophy, winning Season 16 of Dancing With the Stars. She was later inducted into the North Carolina Music Hall of Fame.
From 2017 to 2019, Pickler co-hosted the nationally syndicated talk show Pickler & Ben, which earned five Emmy nominations. She has also expanded into acting, appearing in a variety of films and TV shows, including Christmas at Graceland, The Mistletoe Secret, 90210, Billy Lynn’s Long Halftime Walk, and Wedding at Graceland.
Kellie Pickler has largely stayed out of the public eye in recent years. Her last public appearance came in April 2024, when she stepped onto the stage at the Ryman Auditorium for a tribute performance honoring Patsy Cline. The moment marked her first appearance since the passing of her husband, songwriter Kyle Jacobs, who died at the couple’s Nashville home on February 17, 2023.
Monday night’s episode also featured original Idol judges Paula Abdul and Randy Jackson, appearing as guest judge and guest mentor, respectively. Dancing with the Stars pros, adding a touch of ballroom flair to the celebration, while America voted live to narrow the Top 5 down to the Top 3.
The American Idol grand finale is set for May 11, 2026, when the remaining finalists will take the stage one last time to earn America’s votes. Alicia Keys will serve as guest mentor and perform, with additional “music legends” set to be announced soon.
