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Top 5 Kellie Pickler Songs

Kellie Pickler
Ethan Miller, Getty Images

Kellie Pickler has been rolling out great songs since finishing sixth on Season 5 of ‘American Idol’ — and she’s come a long way. The 28-year-old has since made quite a name for herself. Her debut, the 2006 ‘Small Town Girl,’ produced three Top 20 hits. These are just a handful of the best Kellie Pickler songs.

Black River Entertainment
Black River Entertainment


‘The Woman I Am’

From ‘The Woman I Am’ (2013)



The title track from Pickler’s 2013 album ‘The Woman I Am’ almost didn’t make it onto the record. The singer and her husband, Kyle Jacobs, wrote the song together after the album was complete. With a chorus belting, “I’m stubborn and proud / And get loud with a beer in my hand / Sometimes I curse too much ’cause I don’t give a damn / And that’s the woman I am,” you can’t help but cheer Pickler on as she continues the journey in becoming the woman — and star — that she’s meant to be.




‘Don’t You Know You’re Beautiful’

From ‘Kellie Pickler’ (2008)



On this song, Pickler used her position as a role model to speak to young girls. She addresses self-worth and beauty in the poignant, mid-tempo track, and with every listen, women of all ages gain strength and confidence through Pickler’s true words and honeyed vocals.




‘Best Days of Your Life’

From ‘Kellie Pickler’ (2008)



Co-written by Pickler and Taylor Swift, ‘Best Days of Your Life’ off her eponymous 2008 record is upbeat, electric and utterly addictive — much like the singer herself. Pickler admits that the song is based on a true story, and Swift encouraged her to write about it while they were on tour with Brad Paisley. ‘Best Days of Your Life’ was Pickler’s first Top 10 hit on the country charts and her first Platinum track. It’s a must-have on this Best Kellie Pickler Songs list.


Black River Entertainment
Black River Entertainment


‘Someone Somewhere Tonight’

From ‘The Woman I Am’ (2013)



This song was originally recorded by other artists, including Kenny Rogers and Pam Tillis, but Pickler brought it new life as the first single from her fourth album. She describes it as her favorite song she’s ever cut, and we can see why. As opposed to many of her other heartfelt songs, ‘Someone Somewhere Tonight’ is hopeful and joyful, instead of pain-filled and heartbreaking. The music video was also a treat, and Pickler showcased her enviable dance moves with ‘DWTS’ partner Derek Hough.




‘I Wonder’

From ‘Small Town Girl’ (2006)



Pickler has been audible about her tumultuous childhood, which included (or rather, didn’t include) an absent mother and an alcoholic father. ‘I Wonder,’ which Pickler co-wrote, is written from the eyes of a child, and the songstress digs deep into her emotions to sing this autobiographical ballad, which is arguably the best Kellie Pickler song ever. Her tearful performance of ‘I Wonder’ at the 2007 CMAs was easily one of the most touching performances the awards show has ever seen.


Next: See Kellie Pickler in a Bikini!

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