No Artist Has Ever Had a Career on the Billboard Charts Like Billy Ray Cyrus

Ebet Roberts/Redferns
Billy Ray Cyrus photographed circa 1992.

As you almost certainly know by now if you've been paying attention to the story currently overtaking the entire music industry, Lil Nas X's "Old Town Road" is No. 1 on the Billboard Hot 100 this week for a second week -- and now, the 20-year-old rapper is joined in chart-topping credit by his featured partner on the song, via its new remix: 57-year-old country star Billy Ray Cyrus.

While Lil Nas X has been making new chart history with his first-ever Billboard chart entry seemingly every week now, being No. 1 on the Hot 100 for the first time marks an unexpected late-career peak for Cyrus, who now has one of the most interesting chart resumés of any artist in Billboard history.

Of course, Billy Ray Cyrus first broke out on the national scale in 1992 with his debut single "Achy Breaky Heart." Thanks to a supremely catchy chorus and a video that made line dancing a nationwide phenomenon, "Heart" charged all the way to No. 4 on the Hot 100 -- an exceedingly rare country crossover hit for the early '90s, when genre stars like Garth Brooks and Brooks & Dunn were largely siloed from the Hot 100. Though Cyrus later grew a reputation in the mainstream as a one-hit wonder, that would undersell the stratospheric success of "Heart" parent album Some Gave All, which spawned another pair of top 10 hits on Billboard's Hot Country Songs chart (where "Heart" reigned for five weeks), topped the Billboard 200 albums chart for a staggering 17 consecutive weeks, and has sold 7.5 million copies in the U.S., according to Nielsen Music.

But it is true that none of the album's follow-up singles crossed over in nearly the same way -- nor did the singles from any subsequent Billy Ray Cyrus album. He had further country success: Both "In the Heart of a Woman" (from 1993's It Won't Be the Last) and "Busy Man" (from 1998's Shot Full of Love) hit the Hot Country Songs top five, but neither reached higher than No. 46 on the Hot 100. Indeed, 27 years after "Achy Breaky Heart," Billy Ray has yet to send a solo single back to the chart's top 40. 

That's not to say he's been totally absent from the region, though. After largely fading from commercial radio at the outset of the early 21st century, Billy Ray made a pronounced return to the charts in the late '00s, thanks to the boost in exposure provided by his role as Robby Stewart, father to the title character on the hit Disney show Hannah Montana -- played, of course, by real-life daughter Miley Cyrus. As Miley quickly rose to pop stardom that seemingly surpassed Billy Ray's at his peak, her dad also returned to the Hot 100 for the first time since 2000 with the 2007 father-daughter tearjerker "Ready, Set, Don't Go." While the song was a minor hit in its original solo incarnation, reaching No. 85 on the Hot 100, a second version added Miley to the mix -- which catapulted the song into the top five on Hot Country Songs, as well as into the Hot 100's top 40, where it peaked at No. 37. 

From there, Billy Ray scored another Hot 100 hit with a second Miley duet, "Butterfly Fly Away" (from 2009's Hannah Montana: The Movie), and had some minor country radio success with the singles off 2009's Back to Tennessee album, but again largely receded from the charts as the decade turned to the 2010s. His most pronounced Billboard success this decade came as a guest on 2014's "Achy Breaky 2," a trappy, EDM-flavored redo of Cyrus' signature hit from rapper/producer Buck 22, which got to No. 80 on the Hot 100 -- and No. 11 on Hot Rap Songs, marking Cyrus' first visit to the genre ranking.

That collab would presage the song that would improbably take Cyrus all the way to the top of the Hot 100, three spots higher than he even managed with "Achy Breaky Heart." As early as December of 2018, Lil Nas X was tweeting his desire to get the country vet on the remix to his debut single, "Old Town Road" -- despite "Heart" mania occurring seven years before his birth, he was familiar with Billy Ray from watching Hannah Montana growing up. Earlier this April, the rapper born Montero Lamar Hill finally got his wish, as Cyrus offered an extra hook and an original verse to the viral smash. The song's new version drew rave reviews on social media, and quickly outpaced the original in overall Hot 100 chart metrics, on its way to securing "Old Town Road" a resounding second week at No. 1, including a record-shattering 143 million U.S. streams in the latest tracking week.

Now, Billy Ray Cyrus has his first Hot 100 No. 1 hit at age 57 -- making him one of the oldest artists to reach the top spot for the first time, though still five years behind Louis Armstrong, who first topped the chart (at age 62) with "Hello, Dolly!" in 1964. Cyrus also ranks just behind Santana's 30-year span between his first Hot 100 entry (1969's "Jingo") and first No. 1 with his own 27-year gap between "Achy Breaky Heart" and "Old Town Road." And along with daughter Miley, who topped the Hot 100 with her own "Wrecking Ball" in 2013, he joins an exclusive group of fathers and daughters who have led the Hot 100, a family tree whose branches include Frank and Nancy Sinatra, Pat and Debby Boone, John and Chynna Phillips, and Brian and both Carnie and Wendy Wilson

Perhaps most interesting and rare of all: Billy Ray Cyrus now has visited the Hot 100's top 40 exactly three times, and each of those times in a different decade: "Achy Breaky Heart" in the '90s, "Ready, Set, Don't Go" in the '00s, and "Old Town Road" in the '10s. You might think that if an artist were to pull off such an unusual chart feat, they'd do it by straddling the line on two of those decades -- like, say, hits in 1999, 2001 and 2010 -- but Billy Ray's three hits have over a decade of distance between each of them, coming in 1992, 2008, and now 2019.

It's an extremely impressive run of longevity from an artist who's never been able to maintain a sustained run at the core of the mainstream, but it's a testament to an artist who found early-career kinship with Kurt Cobain and is now offering veteran wisdom to Lil Nas X that he's been able to keep finding his way back there nonetheless. When Billy Ray Cyrus sings on the "Old Town Road" remix that he's gonna ride till he can't no more, you really have to take his word for it.