Top 10 Kellie Pickler Songs

Feature Photo: Featureflash Photo Agency

Our top 10 Kellie Pickler songs list looks at the body of work of an American Idol alum renowned for her impactful contemporary country music career. At the TV show, Kellie Pickler performed songs by reputable artists such as Bonnie Raitt, Melissa Etheridge, Bobbie Gentry, Patsy Cline, and Vivienne Segal. Before she was eliminated, Kellie Pickler took on the love song “Unchained Melody” by Todd Duncan.

Despite finishing sixth in the fifth season of American Idol, Kellie Pickler had already attracted a cult following. Kellie Pickler’s fame and popularity saw her picked signed by BNA Records. The singer-songwriter started her solo career, releasing breakout hits that catapulted her to global fame.

Kellie Pickler’s Career Beginnings and Breakthrough

After signing a recording contract with BNA Records, the country singer released her debut single “Red High Heels” in 2006. “Red High Heels” brought Kellie Pickler to newfound fame, rising to number sixty-four on the Billboard Hot 100. The song was also Gold-certified after its sales shot to above five hundred thousand copies.

“Red High Heels” only opened the way to Kellie Pickler’s debut album, Small Town Girl. Kellie Pickler issued the LP almost a month later, featuring another dazzling hit, including “I Wonder” and “Things That Never Crossed a Man’s Mind.” Small Town Girl saw Kellie Pickler become among the few reputable artists to receive the top ranking on the Billboard Top Country Albums chart. The LP managed to rise to the ninth spot on the Billboard 200. Small Town Girl was finally certified Gold marking Kellie Pickler’s success in the country music scene. The album has sold more than nine hundred thousand copies to date.

Kellie Pickler’s Album Releases over the Years

After the success of her 2006 LP Small Town Girl, Kellie Pickler hit the studio to record her eponymous sophomore LP. Kellie Pickler was also a massive release, topping the Billboard Top Country Albums chart. The LP replicated Small Town Girl’s performance on the charts, also peaking at number nine on the Billboard 200.

While Small Town Girl and Kellie Pickler delivered identical results on the charts, the sophomore album failed to sell as many copies as the debut album. Kellie Pickler is currently about thirty thousand copies away from being Gold certified. The album is home to some of the best Kellie Pickler songs, including “Don’t You Know You’re Beautiful,” “Best Days of Your Life,” “Didn’t You Know How Much I Loved You,” and “Makin’ Me Fall in Love Again.”

Later in 2012, Kellie Pickler returned with her third studio album, 100 Proof. 100 Proof managed the second spot on the Billboard Top Country Albums chart. This was a drop from the top spot, as seen with Kellie Pickler’s debut and sophomore LPs. Nevertheless, 100 Proof outshined Small Town Girl and Kellie Pickler on the Billboard 200, rising to the seventh spot. The mixed performances by the album were also replicated with its songs, having none of its featured hits rise to the Billboard Hot 100. Some of the best Kellie Pickler songs from the LP include “Tough” and the album title track “100 Proof.”

After a mutual agreement not to renew her contract with BNA Records, Kellie Pickler signed to Black River Entertainment. Her song “Someone Somewhere Tonight” marked Kellie Pickler’s debut hit on her new record label. The song served as the lead track to Kellie Pickler’s fourth LP, The Woman I Am. Other musical gems from the LP include “Little Bit Gypsy” and “Closer to Nowhere.” The Woman I Am topped the Billboard Independent Albums chart. It also managed to rise to the fourth and nineteenth spot on the Billboard Top Country Albums chart and Billboard 200.

The Woman I Am is the most recent LP release by Kellie Pickler. However, the female country artist has released three other promotional singles, including “The Man with the Bag” in 2013, “Feeling Tonight” in 2015, and “If It Wasn’t for a Woman” in 2017. Eventually, Kellie Pickler left Black River Records in 2016.

Kellie Pickler’s Other Musical Pursuits

In the early stages of her career, Kellie Pickler interacted with tons of artists, cementing her reputation as a top-tier artist in the country scene. In 2007, she took part in Brad Paisley’s concert tour and later featured in the accompanying music video to his song “Online.” Kellie Pickler has also accompanied Rascal Flatts, Sugarland, and Taylor Swift on their musical tours. The singer would later get involved in the sixteenth season of the TV series Dancing with the Stars, where she was announced the winner alongside ballroom dancer Derek Hough.

Kellie Pickler’s Accolades and Legacy

The country singer received her first CMT Music Awards nomination for the Breakthrough Video of the Year award in 2007, credit to her debut hit “Red High Heels.” Other nominations that happened in the same year include the Academy of Country Music Awards for the Top New Female Vocalist of the Year and the Country Music Association Awards for the Horizon Award.

Kellie Pickler won the American Society of Composers, Authors, and Publishers’ accolade for the Songwriter Award category, credit to “Red High Heels.” In 2008, the country singer won three CMT Music Awards thanks to her single “I Wonder.” The awards were under the Performance of the Year, Tearjerker Video of the Year, and Breakthrough Video of the Year categories.

Once more, Kellie Pickler won the Songwriter Award in the 2008 American Society of Composers, Authors, and Publishers ceremony credit to the song “I Wonder.” The singer won a similar award in 2010, thanks to her single “Best Days of Your Life.” The singer has a string of nominations for awards that help back up her excellence in the country music scene. In 2016, Kellie Pickler was inducted into the North Carolina Music Hall of Fame.

Despite not being active since her last album, her success in the country scene placed her among the most successful American Idol alumna. On Valentine’s Day 2022, Kellie Pickler joined SiriusXM’s The Highway show, expressing to the world her excitement with the chance she got to interact with country music fans. Here are the ten best Kellie Pickler songs from her magnificent country music career.

#10 – 100 Proof

Opening our top 10 Kellie Pickler songs list is the splendid hit “100 Proof.” The song is the album title track to Kellie Pickler’s third LP. “100 Proof” had its lyrics penned by James T. Slater and Leslie Satcher. The song was recorded in a quaint manner, with the singer and her accompanying musicians all in a single room.

Kellie Pickler revealed in an interview that the song alludes to two diverse relationships. In the song, the singer describes an unhappy relationship between her friends, comparing it with her relationship, which she reveals to have been fine and happy. “100 Proof” peaked at number fifty on the Billboard Hot Country Songs chart.

#9 – Santa Baby

Our top 10 Kellie Pickler songs not only feature the singer’s original hit alone. The ninth song on the list finds us digging deeper into Kellie Pickler’s 2007 cover song “Santa Baby.” “Santa Baby” is a 1953 Christmas novelty song released by Eartha Kitt. Kitt performed the song alongside Henri René and His Orchestra.

On September 18, 2007, Kellie Pickler released a country-themed cover of the song. The song was warmly received in the Country scene, with critics praising it for its classic-style arrangement that added glamor to its sonic feel. Her cover version peaked at number thirty-three on both the Billboard Country Airplay and Billboard Hot Country Songs chart. Other artists who have covered the song include Kylie Minogue, Gwen Stefanie, Pink Martini, Taylor Swift, Ariana Grande, Trisha Yearwood, and Michael Bublé.

#8 – Don’t You Know You’re Beautiful

On the eighth spot of our ten best Kellie Pickler songs is the country power ballad “Don’t You Know You’re Beautiful.” The song is among the musical gems featured on her eponymous sophomore LP. Aimee Mayo, Chris Lindsey, and Troy Verges collaborated on penning the lyrics to the song.

“Don’t You Know You’re Beautiful” finds Kellie Pickler reassuring fellow females about their beauty. The song is filled with words alluding to raising one’s self-esteem, reminding them that they are beautiful no matter the flaws they see in themselves.

“Don’t You Know You’re Beautiful” peaked at number twenty-one on the Billboard Hot Country Songs chart. It also rose to the third spot on the Billboard Bubbling Under Hot 100 chart.

#7 – Things That Never Crossed a Man’s Mind

“Things That Never Crossed a Man’s Mind” is one of the best Kellie Pickler songs from her debut LP Small Town Girl. Tim Johnson, Wynn Varble, and Don Poythress are credited with penning the song. Its lyrics allude to the dissimilarities between the male and female gender.

In-depth, the song showcases the mediocre thoughts of women, which most men never get a glimpse of in their lifetime. Surprisingly, the lyrics were done by three men. “Things That Never Crossed a Man’s Mind” rose to number sixteen on the Billboard Hot Country Songs chart. The song also managed the ninety-sixth spot on the Billboard Hot 100.

#6 – Someone Somewhere Tonight

Number six on our top 10 Kellie Pickler songs list is the charming hit “Someone Somewhere Tonight.” Initially, the song was released by Walt Wilkins on his LP, Mustang Island, issued in 2005. Kellie Pickler later covered and released the song as her lead single to her fourth LP, The Woman I Am.

The song finds Kellie Pickler crooning about the supreme might of redemption and affection. Kellie Pickler’s cover version is lauded by many for its amazing and heartrending performance. Her version peaked at number forty-nine on the Billboard Country Airplay chart. Other artists to have covered the song include Kenny Rogers, Pam Tillis, and Mark Blomsteel.

#5- Tough

100 Proof is home to our fifth pick on our ten best Kellie Pickler songs of all time, “Tough.” The song is a lyrical gem penned by songwriter Leslie Satcher. Leslie has also penned lyrics to songs by notable artists such as Vince Gill, George Strait, Gretchen Wilson, and Martina McBride.

This uptempo anthemic hit finds Kellie Pickler singing about how she has been able to overcome difficulties in her life. Kelly has achieved it all, credit to getting a little tough despite being like any other typical lady. “Tough” peaked at number nineteen on the Billboard Bubbling Under Hot 100.

#4- I Wonder

“I Wonder” is a musical gem that takes us back to the Country chart-topping debut LP Small Town Girl. Kellie Pickler collaborated with Aimee Mayo, Chris Lindsey, and Aimee Mayo in penning the lyrics to the song. The song was inspired by Kellie Pickler’s childhood experiences where she missed her mother.

This piano ballad finds the singer reflecting on her missed moments. The song won three CMT Music Awards in the Performance of the Year, Tearjerker Video of the Year, and Breakthrough Video of the Year categories. “I Wonder” peaked at number fourteen on the Billboard Hot Country Songs chart. On the Billboard Hot 100, “I Wonder” peaked at number seventy-five.

#3- Didn’t You Know How Much I Loved You

On the third spot of our ten best Kellie Pickler songs is the country power ballad “Didn’t You Know How Much I Loved You.” The song is among the musical gems featured on her eponymous sophomore LP. Its lyrics are a collaborative work by Aimee Mayo, Chris Lindsey, and Troy Verges.

“Didn’t You Know How Much I Loved You” finds Kellie Pickler crooning about a broken relationship. In the song, she describes losing the soul she loved the most. What makes the song alluring is her heartfelt vocal delivery that expresses the pain in her heart due to the loss. In the accompanying music video, the singer pours out her emotions by shedding genuine tears, which shows her deep connection with the lyrics she was singing.

“Didn’t You Know How Much I Loved You” peaked at number fourteen on the Billboard Hot Country Songs chart. On the Billboard Hot 100, the song rose to number ninety-seven. A rendition of the song was sung in the eleventh season of American Idol by Skylar Laine. Skylar Laine managed the fifth spot in the competition TV series.

#2 – Best Days of Your Life

Number two on our top 10 Kellie Pickler songs list is the alluring hit “Best Days of Your Life.” The song is the most popular release from Kellie Pickler’s eponymous LP. Kellie Pickler collaborated with her friend Taylor Swift in penning the lyrics to the song, with Taylor Swift providing her vocals in the background.

“Best Days of Your Life” find Kellie Pickler crooning about how her former lover’s infidelity moves. Eventually, the ex-boyfriend moved in with the new mistress, and all that Kellie Pickler wishes for them is the best days in their lives. “Best Day of Your Life” is the only Kellie Pickler song to achieve Platinum certification. The song is also her highest-charting release, peaking t number forty-six on the Billboard Hot 100.

#1- Red High Hills

“Red High Hills” is the debut single by the country female artist Kellie Pickler. The song was penned by Karyn Rochelle, Aimee Mayo, Chris Lindsey, and Kellie Pickler. It was later issued on Kellie Pickler’s debut LP Small Town Girl.

“Red High Heels” is a single ladies’ anthem after they just walk out of their toxic relationships. The song was Kellie Pickler’s first release to earn a Gold certification, becoming her signature single. “Red High Heels” features an aesthetic music video directed by Chris Hicky. Chris Hicky has also directed music videos for other reputable artists such as Florida Georgia Line, Carrie Underwood, Lady Antebellum, and Miranda Lambert. The song peaked at number sixty-four on the Billboard Hot 100.