'90s Country Music Icon Released First No. 1 Hit Song 27 Years After Beginning Career
Billy Ray Cyrus spent decades as one of country music's most recognizable voices before finally earning his first No. 1 hit on the Billboard Hot 100 in 2019.
The country singer, who launched his career with his debut album Some Gave All in 1992, reached the top spot thanks to his feature on Lil Nas X's smash remix of "Old Town Road."
The song became one of the biggest music hits of the decade and gave Cyrus a milestone that had taken 27 years to achieve.
"Old Town Road," originally released independently by Lil Nas X in December 2018, exploded in popularity after going viral on TikTok. The remix featuring Cyrus arrived on April 5, 2019, and quickly climbed the charts.
By April 13, 2019, the song hit No. 1 on the Billboard Hot 100, where it stayed for a record-breaking 19 consecutive weeks.
For Cyrus, the achievement marked a major comeback moment after years of chart success in country music but never reaching the top of the all-genre Hot 100 chart.
His signature 1992 hit "Achy Breaky Heart" had previously peaked at No. 4 on the Billboard Hot 100. While the song became a cultural phenomenon and helped launch a worldwide line-dancing craze, it stopped short of the chart's top position.
Cyrus first entered the music scene in 1992 with the release of Some Gave All. The album became a huge commercial success, debuting at No. 1 on both the Billboard 200 and Top Country Albums charts.
The project produced several hit singles, including "Achy Breaky Heart," "Could've Been Me," and "She's Not Cryin' Anymore." The album eventually sold more than 20 million copies worldwide and became one of the best-selling country debut albums ever released.
Even with his early fame, Cyrus never reached No. 1 on the Billboard Hot 100 during the peak of his '90s popularity.
Over the years, he continued releasing albums, acting in television and movies, and later introduced himself to a younger generation through Disney Channel's Hannah Montana, where he starred alongside his daughter Miley Cyrus.
Still, his career received an unexpected resurgence when Lil Nas X invited him to join the "Old Town Road" remix in 2019.
Cyrus said he immediately connected with the song when he first heard it. He later explained that the lyrics reminded him of the Old Town Bridge in Kentucky, where he spent time as a child.
The collaboration also arrived during controversy surrounding the song's removal from Billboard's Hot Country Songs chart. Billboard stated the track did not contain enough elements of today's country music, sparking widespread debate about genre boundaries and representation in country music.
Cyrus publicly supported Lil Nas X after the decision.
The remix of "Old Town Road" shattered records around the world. The song topped charts in multiple countries, including the United States, Canada, Australia, Germany and the United Kingdom.
It also became the fastest song ever to receive Diamond certification from the Recording Industry Association of America after selling 10 million units in the U.S. The single has since surpassed 17-times Platinum certification in America and sold more than 18 million copies worldwide.
The song blended country, rap, and trap influences, creating a sound that stood out from mainstream radio at the time. Produced by YoungKio, the track sampled Nine Inch Nails' "34 Ghosts IV" and featured banjo sounds mixed with trap-style drums and bass.
Lil Nas X reportedly bought the beat online for just $30 before recording the song in one day.
The success of "Old Town Road" also earned Cyrus his first Grammy Awards. At the 62nd Grammy Awards, the remix won Best Pop Duo/Group Performance and Best Music Video.
The track's historic 19-week run atop the Billboard Hot 100 broke the previous record held by Mariah Carey and Boyz II Men's "One Sweet Day" and Luis Fonsi and Daddy Yankee's "Despacito" remix featuring Justin Bieber.
For Cyrus, the chart-topping moment proved that his music career still had room for new milestones nearly three decades after it began.
Related: Billy Ray Cyrus Reacts to Major Update on 'Hannah Montana 20th Anniversary Special'
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This story was originally published May 1, 2026 at 1:53 AM.