Here Are The Best Kellie Pickler Songs That Caught The Nation’s Attention

Kellie Pickler caught the entire nation’s attention when she hit the stage of American Idol during its fifth season in 2005. Though she finished sixth, the North Carolina native charmed the audiences with her Southern twang and massive ambition. Soon enough, Kellie Pickler songs are playing on the radio to the excitement of country fans. 

Sadly, the acclaimed singer has been laying low since her talk show, Pickler & Ben, came to an end in 2019. We know a lot of fans miss her! So, we’ve gathered some of Kellie Pickler‘s best hits to take a look back at her refreshing musical career. Keep on reading below.

1. I Wonder

Co-written by Pickler herself, “I Wonder” describes her personal experiences during her childhood without a mother by her side and a father that has been in and out of jail. The emotion, misery, and sorrow felt in every lyric truly touched so many hearts that every time she performed it live, she would receive a standing ovation. 

The poignant ballad is also accompanied by a music video shot at Nashville’s Ryman Auditorium – it went on to take home three awards during the 2008 CMT Music Awards.

2. Someone Somewhere Tonight

The song was originally recorded by Walt Wilkins in 2005. Since then, it has been covered by several artists – this includes Kenny Rogers, Pam Tillis, and of course, Pickler – who said that it’s her favorite song that she has ever cut and released to country radio. 

“Someone Somewhere Tonight,” tells the point of view of a lover. She sings to her significant other as she looks into the different things people in the world are experiencing at the same time. Pickler believed people need to hear it to give them hope that finding a soulmate is possible.

3. Best Days of Your Life

When Pickler and Taylor Swift hit the road for a tour with Brad Paisley during the early days of their career, the two became fast friends and collaborated on a breakup ballad about a relationship that went sour – inspired by Pickler’s own love life.

Swift then joined Pickler to provide background vocals for the track and even appeared in the music video.

4. Red High Heels

Pickler showed her fierce side in this sassy track! Frustrated by a troubled past with a former lover, Pickler told him she would move on with her red high heels. It has since become one of her signature songs, especially that the singer loves collecting shoes.

5. Didn’t You Know How Much I Loved You

This powerful ballad finds Pickler describing the feeling of losing a lover you deeply love. It first appeared on Pickler’s debut album, Small Town Girl. However, Pickler insisted on releasing the song as a single – so she re-recorded it for her self-titled sophomore album.

6. Things That Never Cross a Man’s Mind

The third and final single off her debut album, this up-tempo ballad playfully describes the differences between men and women by listing down things that a woman could think of on a regular basis – but would never cross a man’s mind. What’s surprising was that the song was written by three male songwriters.

7. Don’t You Know You’re Beautiful

Pickler debuted the song during the 43rd annual Academy of Country Music Awards, and it definitely took everyone’s breath away. “Don’t You Know You’re Beautiful” finds Pickler assuring other women that they are beautiful just the way they are. The powerful message definitely speaks to female country fans that admire Pickler. 

8. Makin’ Me Fall in Love Again

Pickler now sings the euphoria of being in love! Despite being told that it will fade, she still finds love invigorating every time she’s with her lover. 

In one interview, Pickler revealed that the song is a reflection of her relationship at the time. But what’s more interesting was that it almost did not make it to her album and was almost shelved. Pickler noted that it was the last song they recorded for her self-titled second album.

9. Tough

Though Pickler did not write the song, the singer revealed that it was somewhat autobiographical and even summed up her personality. The powerful ballad finds Pickler singing about how she’s been able to overcome life’s challenges despite being just a regular girl. 

It comes with a poignant music video that reflects Pickler’s troublesome childhood. 

10. Little Bit Gypsy

Kellie maintains her classic country sensibilities in this funny song where she gives her man a warning, letting him know that she won’t be tied down anytime soon. It was actually co-written by Pickler’s husband, Kyle Jacobs.

More Of Kellie Pickler Songs You Need To Listen

Indeed, Kellie Pickler’s truck-sized twang gave us more songs to enjoy. You can find them below!

So, which among these are your favorite Kellie Pickler songs?