A career-defining song almost went to another artist
When Rascal Flatts released “What Hurts The Most” in 2006, it became one of the most emotional and successful singles in modern country music. But according to bassist Jay DeMarcus, the band nearly missed out on the song entirely because it was originally being considered by Keith Urban.
Producer Dann Huff held the song for the right moment
Speaking with Audacy’s Katie Neal, DeMarcus explained that legendary producer Dann Huff brought the song to Rascal Flatts while they were shaping what would become their landmark album Me and My Gang. Although the track had previously been recorded by Mark Wills in 2003, Huff believed it still had untapped potential.
Huff had originally held the song for Keith Urban, but after Urban passed on recording it, the producer felt Rascal Flatts were the perfect fit. According to DeMarcus, Huff told them plainly that while the song had a history, he believed the trio could elevate it to another level.
An instant gut reaction from the band
As soon as DeMarcus, Gary LeVox, and Joe Don Rooney heard the chorus written by Jeffrey Steele, they knew it was special. DeMarcus described it as a “no-brainer,” recalling that the song stood head and shoulders above everything else they were considering at the time.
That instinct proved correct. “What Hurts The Most” went on to become Rascal Flatts’ fifth No. 1 on Billboard’s Hot Country Songs chart, their first Top 10 hit on the all-genre Billboard Hot 100, and a No. 1 on the Adult Contemporary chart. The song also earned two Grammy nominations and helped redefine the band’s career trajectory.
Capturing lightning in a bottle
DeMarcus reflected that Rascal Flatts were never precious about who wrote a song, only about choosing the strongest one. In his words, “What Hurts The Most” felt like capturing “lightning in a bottle,” a moment where everything aligned creatively and emotionally.
The band also faced the challenge of honoring the song’s raw vulnerability. Written by Jeffrey Steele and inspired by his love for his youngest daughter, the demo carried deep emotional weight. DeMarcus credited Gary LeVox’s vocal performance for successfully translating that intimacy into a version that resonated with millions.
A cornerstone of Me and My Gang
Released as the lead single from Me and My Gang, the song helped propel the album to massive success. The project became both the best-selling country album and the best-selling album overall of 2006, eventually reaching 4x platinum status. It also featured other defining tracks like “Stand,” “My Wish,” and Rascal Flatts’ cover of “Life Is A Highway.”
A Grammy moment that changed everything
DeMarcus recalled a powerful memory from the Grammy Awards that underscored just how big the album had become. Sitting among global superstars like Beyoncé, Jay-Z, Lady Gaga, and Elton John, Gary LeVox leaned over and reminded him that Me and My Gang had sold more records than any album in the world that year.
For DeMarcus, that realization remains one of the most emotional moments of his career—a reminder that childhood dreams of success had been surpassed in ways he never imagined.
A legacy that still resonates
Nearly two decades later, “What Hurts The Most” remains one of Rascal Flatts’ most beloved songs, a testament to timing, instinct, and emotional honesty. Had Keith Urban chosen to record it, the song’s legacy might have sounded very different. Instead, Rascal Flatts’ harmonies and vulnerability turned it into a generational anthem.
As the band continues touring and reconnecting with fans in 2026, the story behind “What Hurts The Most” stands as a reminder that sometimes the biggest hits are born from near-misses—and the courage to trust your gut at exactly the right moment.
