Kellie Pickler Has Had Quite The Transformation

The following article mentions suicide, substance misuse, and domestic abuse.

Kellie Pickler is perhaps best known for competing on "American Idol," but that's far from the only thing the country singer has done. She's a true Renaissance woman, someone who's determined to conquer every aspect of the entertainment industry. "I feel that today in the entertainment world it's all about building your brand," she told Broadway World in 2016. "I don't think it's about limiting yourself to just one profession. I think you can do it all."

Pickler has, indeed, done it all. (Okay, except maybe Broadway ... though she hopes to get there someday.) She's been a singer and an actor; she's been the host of both radio shows and talk shows; and she's been a reality television mainstay across three different shows.

While it may seem like Pickler is on top of the entertainment world, her life has also been marked by tragedy, from a difficult upbringing in North Carolina to more recent losses that have defined her personal life. Her career has been one of constant reinvention and transformation, but Pickler herself has had to transform. She's had to find the inner strength to just keep moving when the world seems set against her. "Everyone pays their dues in different ways," she told The Oregonian. "When you're in this business for a while, you're always going to have to pay your dues. Nothing is going to be handed to you." Here's how Kellie Pickler did it.

Kellie Pickler was born in 1986, and she grew up in Albemarle, North Carolina. When she was only 2, her mother, Cynthia Morton, left the family; she regained custody for another two years, but then disappeared for good. In her song "I Wonder," Pickler would later sing, "Did you think I didn't need you here? / To hold my hand, to dry my tears / Did you even miss me, through the years at all?" 

Morton addressed exactly that when her daughter became famous, offering a justification for why she'd been absent while Pickler was growing up. "I'm not as bad as they say," she insisted, detailing a past filled with domestic abuse (via StarNews Online). Morton added, "I just made bad choices."

Because Pickler's mother wasn't around, she was instead raised in her early years by her father, who struggled with alcoholism and frequently spent time in jail. "It was a battle to have to go and visit him in the penitentiary as a child, but that was so normal for me," Pickler later told The Boot. "Looking at it now, as an adult, that's not normal." As both of her parents struggled, Pickler was left to essentially raise herself and her siblings. "When you grow up around the drugs and the alcohol and that kind of abuse, the people that you interact with, drug dealers," she reflected, "there's a lot of stuff that people don't know."

When she was 12, Kellie Pickler and her siblings were handed over to the care of her grandparents. Suddenly, her family life was very different than what she'd known, because she now had support. Pickler became particularly close with her grandmother, whose book of children's hymns shaped her love of music. "Grandma and I would sit together on the porch with that book in our laps and sing our way right through it," Pickler later wrote in an essay for Guideposts. "I got lost in those songs. If I was feeling sad, mixed-up or scared before we started, by the time we were a couple bars in, my troubles took a backseat."

Her grandfather, too, encouraged her love of singing. Pickler told Rolling Stone that he was a big fan of Hank Williams Sr., and when she helped her grandpa out on his construction jobs, they would sing together. "It's one of my most fond memories as a child, being with my grandpa in his big red work truck and being his little assistant, handing him tools," she said. "I was such a little tomboy."

When Pickler was 15, her grandmother died of lung cancer the day after receiving her diagnosis. In her essay for Guideposts, Pickler wrote, "If I thought I knew what emptiness felt like before, I was wrong."

In 2006, when Kellie Pickler was 19, she participated in the 5th season of "American Idol." She later told Bella Online that she was nervous when she saw how many people were trying out. "My grandfather went with me to the auditions," she said. "It was very intimidating, but my grandfather said, 'Kellie, what do you have to lose?' I'm so glad I stuck in there." It's a good thing she stuck it out, because Pickler did very well on the show. The country sweetheart ultimately came in 6th place, losing out to Taylor Hicks, though she won legions of fans all her own. One of those fans was the notoriously ornery Simon Cowell. 

In fact, the "American Idol" judge told Pickler that he preferred her over Season 4 winner and fellow country artist Carrie Underwood. "I would never say that about someone because I imagine it probably hurt her feelings," Pickler told Entertainment Weekly. "At the same time, I know she knew it's just a TV show and it's about ratings. You can't take what they say personally."

Years later, looking back on her time on the reality juggernaut, Pickler made sure to credit what she believes to be the source of her success. She told E! News, "['Idol'] was obviously the rocket that launched my career, but it was God that was the fuel."

After her "American Idol" season concluded, Kellie Pickler embarked on a live concert tour with her fellow finalists. At the same time, over the phone with producers, she was writing what would become her debut album "Small Town Girl." She told All Your TV, "I'd never really written songs before. But it's what your life is about, your feelings, your emotions. The songs I wrote all have special meaning to me, they show what's in my heart and in my thoughts." Pickler wanted her debut album to be very personal, as is often the case with country music.

Pickler's candor paid off, and the album — released later in 2006 — became a hit, selling more than 900,000 copies. The album spawned hits like "Red High Heels," "I Wonder," and "Things That Never Cross A Man's Mind," all of which hit the Top 20 on the Billboard Country Airplay charts.

In other words, Pickler's life changed quickly, and her country stardom had even more of an effect on her life than her early "Idol" success. Pickler revealed to Bella Online that she'd moved to Nashville and was heavily involved in her career. "This is my life now," she reflected. "Right now I'm paying my dues as a new country artist. I see my family when I can. They know this is my lifelong passion and dream."

After her time on "American Idol," fans started to speculate about Kellie Pickler's physical appearance — namely, whether or not she'd had a breast augmentation. When Pickler stopped by Ryan Seacrest's radio show in 2007 (via People), the two got into a back-and-forth about her décolletage. "Are you talking about my boobs again? Why are you looking at my boobs anyways?" Pickler teased Seacrest. He responded, "I'm not looking at them, America is looking at them."

The "Idol" host came right out and asked her whether she'd gone under the knife, and Pickler played coy. "I like to be the center of attention, and right now me and the girls, we are pretty much getting a lot of attention," she said.

In 2008, the conversation was still ongoing. At an "American Idol" event that Pickler attended, "Idol" producer Nigel Lythgoe told Fox News that her new look was to blame for her successful career. "She's acquired two accoutrements that (naturally) photographers and men love," he said. (Yikes.) This time, Pickler seemed to finally admit that she'd had surgery. Fox News indicated that she gestured to her breasts while explaining that she'd changed in the years since her debut album was released. "Let's just say I feel much more mature now," she said.

Early on in both of their careers, Kellie Pickler linked up with another young country artist by the name of Taylor Swift. The future global superstar co-wrote Pickler's song "Best Days Of Your Life," singing background and even making an appearance in the song's music video. It wound up becoming Pickler's biggest hit, peaking at #46 on the Billboard Hot 100 and reaching the Top 10 on the Country Airplay chart. 

In 2009, Pickler opened for Swift on the Fearless Tour. The twosome told The Boot that they'd become quite close while touring, even considering each other sisters. "I have the most fun with Taylor after the show, when we can just sit in our PJs and talk. It's just girl talk, you know?" Pickler said. Swift agreed, gushing, "I can trust Kellie with all my secrets because she's really unbiased."

It's unclear whether the two are still close. Pickler sang Swift's praises on "Larry King Now" in 2015, telling the host, "She's very talented. She's one of the most incredible songwriters, she's a great entertainer, and she's, I think, really marketed herself and protected her brand." A few years later, however, Pickler denied being part of Swift's infamous "Squad" in an interview with FOX411. "I'm not a part of any squad, per se," she laughed. "I'm just kind of my own little thing." 

Taylor Swift wasn't the only songwriter Kellie Pickler bonded with early in her career. She also got to know Kyle Jacobs, the man behind country hits like Garth Brooks' 2007 smash "More Than A Memory." After striking up a relationship, Jacobs proposed to Pickler in 2010. The venue he chose for the romantic question was a picturesque beach setting, but his timing might have been seen as questionable. Pickler told People that June 15th was the anniversary of her grandmother's death, and that's the day Jacobs chose to get down on one knee. Thankfully, rather than making her more upset, she felt that they had her grandmother's blessing. "It turned out to be the most amazing day of my life," she told the outlet. Jacobs added, "Afterward, we just held each other and had the most beautiful prayer. We had a little champagne and talked and laughed and cried."

They eloped on New Year's Day 2011. Pickler later admitted on "The Ellen DeGeneres Show" (via the Los Angeles Times) that she got fed up with planning her wedding, realizing that she didn't even like most of the people they planned to invite. They ran away to the Caribbean and got married on a whim. "We totally just put faith in God that it was all going to work out and it did," she gushed. "And it was the most incredible day of my life."

In 2013, Kellie Pickler made a grand return to reality television when she competed on the 16th season of "Dancing With The Stars." Sporting a close-cropped pixie cut, Pickler and her partner, Derek Hough, wowed the judges each week with their commitment to various forms of dance. Fans loved the behind-the-scenes banter between the two, such as one interview where Pickler told E! News, "It is very physically demanding. But you're working muscles, or, I'm working muscles that I've never worked before ... I'm definitely sore, but I guess no pain no gain!" Gesturing toward Pickler's head, Hough teased, "Definitely working muscles she hasn't worked before."

The pair went on to win the whole season, beating fan-favorites like Zendaya for the iconic mirrorball trophy. Pickler's grandfather supported this next chapter in her reality TV journey. The singer told "Good Morning America" that "Dancing With The Stars" is his favorite show, and he was at the finale when she won. "It was so great, because he actually talked me into doing the show," she said. "[The trophy is] going in his bedroom, he said, on his nightstand."

Pickler later told Broadway World that she had a blast, discovering a love for the art of dance that she'd never expected. "Well that was by far my favorite thing I've ever participated in as far as television projects go," she said. "I would do it again in a heartbeat!"

In 2015, country superstar Carrie Underwood gave birth to her first child, a boy named Isaiah. At that point, Underwood's friendship with Kellie Pickler was well-publicized, and the latter started to get questions about whether she'd be joining her friend in starting her own family. Speaking with OK! magazine, Pickler said that no, she didn't plan on having any kids of her own. "It's so exciting for Carrie, but I don't want the responsibility of raising a human being," she said, insisting that she would be perfectly okay with just being "Aunt Kellie."

Along those same lines, Pickler told Us Weekly in 2019 that she and her husband were focused on their fur babies rather than planning for any human babies. "We have two little small puppies," she said. "We're dog parents for now."

The following year, at the height of the COVID-19 pandemic in 2020, Pickler was once again grilled about her future plans when Us Weekly asked whether she and her husband wanted to join in on the pandemic baby boom. During a round of the magazine's Zoom game "Quarantine Confessions," Pickler asked, eyes wide, "A quarantine baby boom? Is that a thing?" As her off-camera husband joked about needing a drink, Pickler answered emphatically, "No. I love being Aunt Kellie, and that is perfect for me." 

Though she'd made her mark on the country music scene, Kellie Pickler couldn't resist returning to her roots: reality television. Between 2015 and 2016, Pickler and husband Kyle Jacobs anchored a CMT reality show called "I Love Kellie Pickler." The series gave them the perfect opportunity to enjoy married life together, she told Broadway World. "My husband and I, we actually get to see each other a lot more now because we get to work together on the show," she said. "It's given us the chance to capture our fun memories that we've made with our friends, who we consider to be our family."

When that reality show ended, another TV series began. In 2017, Pickler launched a new daytime talk show called "Pickler & Ben," which she would end up hosting for two years alongside Ben Aaron. She told The Boot that she was sold on the show as soon as they pitched her the concept: it would shoot in Nashville, and it would focus on good things. "It's positive, uplifting, a lifestyle talk show, and we get to shine a light on people in the community doing do great things," she said. "I fell in love with it instantly."

Though the show only lasted two seasons, it was critically acclaimed. "Pickler & Ben" was nominated for five Daytime Emmys. Pickler picked up two nods for Outstanding Informative Talk Show Host. Unfortunately, they didn't win any.

Early in her career, Kellie Pickler told Bella Online that her entertainment industry idol was none other than Dolly Parton. Like the "9 to 5" star, Pickler said she hoped to someday move into acting, too. "She's an incredible singer, songwriter, performer and has the best personality. She can act. She's the whole package," Pickler exclaimed.

In the early years of her career, Pickler picked up a few acting roles here and there, including playing herself on a 2014 episode of "Nashville." In 2018, however, the country star finally made the leap into acting when she starred in "Christmas at Graceland," a Hallmark holiday movie. Fittingly, the film's storyline required Pickler to sing, and she told TV Insider that she was honored to have a chance to belt out some Elvis Presley classics. "I cannot believe that this opportunity even came along, but I'm so thankful," she said. "It's really been a wonderful experience and a safe place for me to explore the acting world."

Her film debut went so well that she returned to the network the following year for two more films, a sequel called "Wedding at Graceland" and then another Christmas movie called "The Mistletoe Secret." Pickler Hallmark clearly loved the gigs. As she quipped to MediaVillage, "I'm still a part of the Hallmark family and thankfully they still put up with me."

Ever since 2008, Kellie Pickler has been a regular entertainer on the United Service Organization Tours, an effort to bring entertainment to those serving in the military overseas. When she headlined the 2014 USO Gala, she told the organization, "I've been so blessed to be able to do what I love and travel, and sing my little songs, and take my little songs overseas and entertain the troops. It's life-changing."

In 2021, Pickler took on a new role when she was named a USO Global Ambassador alongside "That '70s Show" star Wilmer Valderrama. "The USO has allowed me so many opportunities to serve those who serve us, and this is another way I can help shine a light on something that matters," she said in a press release published by Sounds Like Nashville. She spoke with the same outlet about a campaign she was working on for the USO, called Give More Thanks. 2019 was the organization's 80th Anniversary, and they released commemorative t-shirts to raise funds to support the troops. "You can get your t-shirt and we can be twins!" Pickler said. "It's a beautiful thing to be a part of."

Not content to let any area of the entertainment industry go unexplored, Kellie Pickler picked up a new gig in 2022 when she joined the SiriusXM family. Pickler became a regular DJ on their country music station "The Highway." In a statement on the SiriusXM website, Pickler shared her enthusiasm for her latest career transformation. "This is such a fun and amazing opportunity to really connect with country music fans across North America," she said. "I'm looking forward to sharing some of my current favorite songs and artists, along with chatting with some very special guests!"

Unfortunately, the gig did not last. In April 2023, radio personality Macie Banks announced on Instagram that she was taking over Pickler's former time slot. Fans speculated that Pickler's absence from the radio might have something to do with a personal tragedy she'd suffered in the meantime — see below — but a SiriusXM representative told CountryNow that that wasn't the case. Instead, they said, her contract had simply run out.

In February 2023, Kellie Pickler's husband, Kyle Jacobs, was found dead. In May, an autopsy confirmed that he had died by suicide.

In the year since her tragic loss, Pickler has relied on friends, family, and fans to get her through. As reported by Realtor.com, she put their Nashville home on the market for $2,890,000, and she has also allowed Jacobs' parents to manage his estate. A lawyer named Goldie Schon told InTouch Weekly that she assumed that move was "to ensure that Kyle's estate receives all funds the estate is entitled to, pursuant to various contracts, copyrights and royalties related to his songwriting or copyrights." 

Pickler sent in a statement to People about how she was coping with her grief, noting that her husband had taught her to remain still when she wasn't sure what to do. "Thank you to my family, friends, and supporters, for the countless letters, calls, and messages that you have sent my way," she said. "It has truly touched my soul and it's helping me get through the darkest time in my life. As many of you have told me, you are all in my prayers."

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