The 10 Best Kellie Pickler Songs of All-Time

Kellie Pickler is a country music singer, songwriter, and television personality who first rose to fame as a contestant on the fifth season of American Idol. She has released five studio albums, all certified Gold or higher by the RIAA. In addition to her music career, Pickler has starred in the television series Dancing with the Stars, Celebrity Apprentice, and I Love Kellie Pickler. Over the years, she has become known for her relatable, down-to-earth personality and her catchy, heartfelt songs. Here are the 10 best Kellie Pickler songs of all time.

10. Red High Heels (2006)

 

“Red High Heels” is the debut single from Kellie Pickler’s album Small Town Girl. The song was co-written by Pickler and songwriter Chris Lindsey. “Red High Heels” peaked at number 12 on the Billboard Hot Country Songs chart and helped Pickler gain mainstream attention. The song’s music video was directed by Roman White and featured Pickler dancing around a city street in a red dress and high heels.

9. Feeling Tonight (2015)

 

Feeling Tonight is a song from Kellie Pickler’s album, The Woman I Am. The song is about a woman trying to move on from a past relationship but finds herself still thinking about the man. The song is written by Pickler, Hillary Lindsey, and Luke Laird. The song is a mid-tempo ballad with a country-pop sound. The lyrics are about a woman struggling to move on from a past relationship. The song was released as the album’s second single on November 13, 2015. The song has been met with positive reviews from critics.

8. Santa Baby (2020)

 

The song “Santa Baby” was released as a digital download in 2020 by Kellie Pickler. It is included in her Christmas album, Country Christmas. The song was written by Joan Javits and Philip Springer and is a cover of the original 1953 version sung by Eartha Kitt. The lyrics talk about how the singer has been good all year and asks for several luxury items for Christmas. The song has generally received positive reviews from critics. Many have praised Pickler’s vocals and called the song a “flirty” and “sexy” Christmas tune. The song peaked at number 21 on the Billboard Holiday Digital Songs chart.

7. Don’t You Know You’re Beautiful (2008)

 

Don’t You Know You’re Beautiful is a song about every woman’s insecurities and how beauty isn’t skin deep. This was Kellie Pickler’s first single off her self-titled album. The song is about Pickler’s insecurities and how she was teased by other kids when she was younger because of her weight. Don’t You Know You’re Beautiful is one of those songs that makes you feel good about yourself. The message is simple but effective: every woman is beautiful, no matter what anyone says. The production is catchy and upbeat, making it impossible not to sing along. And Kellie Pickler’s vocals are perfect for the song, conveying both the vulnerability and strength of the lyrics.

6. Bad Boys Get Me Good (2013)

 

This sassy tune is all about how the bad boys always seem to get the girl in the end. Kellie Pickler puts her spin on things with her funny and relatable lyrics. The song describes how girls usually go for the wrong type of guy and then get hurt. It’s a catchy tune that will have you singing along. The lyrics perfectly capture the feeling of being drawn to bad boys, even though you know you shouldn’t be. If you’re looking for a song that sums up the bad-boy appeal, look no further than “Bad Boys Get Me Good.”

5. Makin’ Me Fall In Love Again (2010)

 

This upbeat song is all about the joys of a new relationship. Pickler sounds happy and in love as she sings about how her new partner makes her feel. The song is a perfect pick-me-up for anyone in a good relationship. The lyrics are simple but effective, and the production is top-notch. They describe Makin’ Me Fall In Love Again as a “feel-good love song.” It’s no wonder it was so popular when it was released.

4. Selma Drye (2013)

 

“Selma Drye” is a song co-written and recorded by American country music artist Kellie Pickler. It was released in May 2013 as the lead single from her album The Woman I Am. The song was written by Pickler, Ben Hayslip, and Jimmy Yeary. The song received mixed reviews from critics. Taste of Country critic Billy Dukes gave the song a thumbs down, saying that it “has a retro feel that feels fresher and more vibrant when other artists attempt it.” However, Dukes praised Pickler’s vocal performance, saying “she sounds great” on the song.

3. Little Bit Gypsy (2013)

 

Little Bit Gypsy is one of the best Kellie Pickler songs. It was released in 2013 as part of her album, The Woman I Am. The song is about a girl who is tired of being underestimated and wants to break out of the mold that others have put her in. She declares herself a little bit gypsy and says that she’s not be held back anymore. The song is up-tempo and has a catchy melody that will stay with you long after hearing it. It’s a great song for anyone who has felt like they’ve been held back and wants to break out and be their person.

2. I Wonder (2006)

 

I Wonder, is a song co-written and recorded by American country artist Kellie Pickler. It was released in September 2006 as the second single from her debut album, Small Town Girl. The song was written by Pickler, Bob DiPiero, and Troy Vergas. What makes I Wonder so great is its relatability. Written by Pickler, Bob DiPiero, and Troy Vergas, the song is about a girl in love with a boy who is in love with someone else. It’s a song about unrequited love and the heartache that comes with it. But what makes the song so great is that it’s not just about unrequited love; it’s a song about hope. The song’s protagonist is hoping that one day, the boy she loves will love her back. And that’s what makes it so great.

1. The Letter (to daddy)(2012)

 

Kellie Pickler sings about the struggles of growing up without a father in her song “The Letter (To Daddy).” The song was released in 2012 as a single from her album 100 Proof. Pickler wrote the song with Monty Powell and Shane McAnally. The song is a touching ballad about a daughter longing for her father’s love and attention. Pickler sings about everything she wishes she could tell her father if he were still alive. She sings about the pain of growing up without a dad and how that has shaped her life.