It’s been said that everyone must find their own path to success but every now and again, country music fosters female vocalists who follow a similar pattern, parlaying parts in film and television into becoming international stars. Dolly Parton traveled this path after receiving global notoriety in the movie 9 to 5. Dottie West’s transition into becoming an international figure came after making guest appearances on TV shows like Love Boat and Hee Haw. One of country music’s newest discoveries Kellie Pickler followed suit, garnering fame as a live performer and recording artist after being a candidate in the fifth season of American Idol and later competing in the sixteenth season of Dancing with the Stars where she won first place with her partner Derek Hough.
Born in Albemarle, North Carolina, Pickler led a cossetted, yet turmoil life, having been bounced back and forth between her divorced parents before finally being raised by her grandparents. Since appearing on American Idol, she has released four studio albums, and her star continues to rise. A Top 10 list of best songs might be premature but she has recorded enough material that’s deserving of being on a Top 10 list.
10. “Red High Heels”
The first single from her debut album Small Town Girl, the track was released in 2006 and proved to be a good fit for Pickler, earning her a songwriter award from the American Society of Composers, Authors and Publishers (ASCAP) in 2007. The song became her calling card, showcasing her fun-loving attitude and independent spirit, giving her an advantage over her competition by displaying her feline and feisty toughness.
9. “Feeling Tonight”
The single has a rocking beat integrated with the traditional country twang of Pickler’s vocals, giving the tune a crossover polish. In the biography on her website, Pickler shares, “When I write a song, I just write about who I am and where I’ve been, where I am and what I’m going through, or about people who have had an impact on me.” The girl, who followed her dreams to country-pop stardom, resonates a starry-eyed look in this track.
8. “Santa Baby”
A favorite Christmas tune performed by the likes of Madonna, Emily West and Eartha Kitt, Pickler’s rendition of the song bodes well with her cheery persona and perky register. Flirty and free, Pickler’s delivery is one for the Best of Christmas tunes ever recorded. The single was released in 2007 by her then-music label 19 Recordings / BNA Records.
7. “Don’t You Know You’re Beautiful”
From her self-titled album released in 2008, the song became an anthem for girls both young and old, advocating a similar theme found in One Direction’s single “What Makes You Beautiful” and Christina Aguilera’s “Beautiful.” The song’s authenticity had a second life in 2012, propelling Pickler’s popularity when she had her head shaved that year as a show of support to victims of cancer like her friend Summer Miller.
6. “Bad Boys Get Me Good”
A duet with Pickler and Jasmine Rae, the southern rock vibe in the foundation of the track brings out the fiery side of Pickler’s persona. The two met while Pickler was performing at the CMC Rocks The Hunter Festival in Australia. They recorded the song for Rae’s 2013 recording If I Want To. The song reached number #1 on the Australian Country Music chart and broke the Top 20 on iTunes USA.
5. “Makin’ Me Fall in Love Again”
Harnessed in a swinging rhythm, the track was written by Karyn Rochelle, James T. Slater, and Shane Stevens and recorded by Pickler for her self-titled album. The song did not experience much commercial success but the catchy hook in the track made it a fun-loving number, a recurring theme in Pickler’s songs. The music video bolstered its positive message set in the 1940s with Pickler surrounded by U.S. military men.
4. “Selma Drye”
A tinge of bluegrass and Celtic folk in the mix, Pickler wrote the song about her pistol-packing, snuff-chewing great-grandmother. The song honors a strong figure steep in Pickler’s ancestry, a female role model that she keeps in her heart. She played a moving performance of the song on Bobby Bones’s radio show in Nashville.
3. “Little Bit Gypsy”
A fun, catchy, bouncy rhythm set to lyrics that reflect a positive outlook about one’s unconventional qualities, this track launched Pickler’s The Woman I Am album in 2013, shortly after her win on Dancing with the Stars. Pickler’s bubbly personality shines through in this number, exhibiting a commercial pop flare in a hybrid that blends elements of country, gypsy and folk. It’s a crossover track that showcases Pickler’s distinct vocal nuances.
2. “I Wonder”
Pickler earned critical acclaim for this song which she wrote for her wayward mother. The song won a CMT Music Award for “Video of the Year” and ASCAP’s Songwriter Award. Echoing her idols like Dolly Parton, Loretta Lynn, and Tammy Wynette, Pickler’s treatment of this sentimental ballad is tender, expressing a forgiving nature in the lyrics.
1. “The Letter (to Daddy)”
From her album 100 Proof, Pickler wrote the sensitive piece about her father, a troubled soul. She reflects in the lyrics, “The bottle took you from me / When I was a child / Robbed me of the love I needed / Robbed me of a smile.” The music video features Michael Keaton in the leading role of her troubled father and closes with images of Pickler and her dad.
The end of Pickler’s ride through international stardom isn’t in sight. In November 2015, she debuted her CMT-TV show I Love Kellie Pickler, a docu-comedy that co-starred her husband Kyle Jacobs. She expanded her portfolio from country music singer-songwriter and live performer to entering the home goods collection market with her company Selma Drye, which sells pieces for the home.
Once known as the country-pop version of Jessica Simpson for her “sweet southern style and ditzy demeanor,” proclaimed by US Weekly, Pickler claimed she hadn’t been exposed to much pop culture while growing up. Ironically, she has become a pop culture figure, honing a country-pop repertoire that bridges southern twang with a polished adult contemporary sheen.
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