This week, for just the third time in the 60-plus-year history of the Billboard Hot 100, a song spent its 15th week atop the chart. That song of course was Lil Nas X's "Old Town Road" — which has also included Billy Ray Cyrus for the 14 weeks since that remix debuted, and which now sits one week away from tying the all-time record for the longest reign atop the marquee chart. 

But will a superstar addition to the song just below "Old Town Road" in the rankings get in the way before Lil Nas X can join the historic rankings of Mariah Carey and Boyz II Men's "One Sweet Day" and Luis Fonsi and Daddy Yankee's Justin Bieber-featuring "Despacito" remix? And what do those songs tell us about what it takes to make this level of Hot 100 history? Billboard staffers debate these questions and more below. 

1. When Lil Nas X first hit the Hot 100's top 40, most of us thought we were being optimistic to say that the song might one day make the top 10. Now at 15 weeks at No. 1 and on the doorstep of Billboard history, what's the biggest thing you think we all underestimated when it comes to Lil Nas X and "Old Town Road"? 

Trevor Anderson: I underestimated nothing! But I think there’s two factors at play here: One, the streaming landscape has slowed a bit in 2019 compared with last year. In 2018, 69 (nice) songs debuted in the top 10 of Billboard’s Streaming Songs chart. A little over halfway through 2019, we’re still only at 25 top 10 debuts, so fewer songs are crash landing like a meteor to shake up the top of the charts out of nowhere.

Second, with the controversial dust surrounding the song mostly settled, a lot of people discovered “Old Town Road” is…a good song! It has clever lyrics, great production and is a step removed from the rest of the crowd, so though most may have expected the song to plummet when the headlines vanished, the fact that the song isn’t just a viral, gossip phenomenon has played into its favor.

Gab Ginsberg: Its longevity, certainly. We can’t forget the other select few songs that come from viral trends or memes, and proved to be more than mere flashes in the musical pan — the dance challenge-driven “Harlem Shake" enjoyed five weeks at No. 1, and the "Macarena," also popularized by a dance craze, spent 14 weeks at the summit. So this has happened before… but for this length of time? Guess we’re really in the new frontier with OTR. The lesson is that in 2019 especially, it doesn’t pay to underestimate the power of meme songs, and the kids who obsess over them for months on end.

Carl Lamarre: To be completely frank with you: The power of Billy Ray Cyrus. Now, that's not to diminish Lil Nas X's hitmaking prowess, but Billy Ray polished an already strong record into a superior gem. We all knew he was a country savant, but to see him attack "Old Town Road" to the point he's doing hip-hop shows, it's honestly just dope and mindboggling to me all at the same time. He's a bad man on that guitar. 

Jason Lipshutz: We all overlooked how damn catchy that hook is. I certainly dismissed the original version of “Old Town Road” as a novelty that could gain some Hot 100 traction thanks to its utilization as a meme, but the reality is that the song’s refrain is a perfect sing-along — simple and immediately memorable, familiar yet unique enough to separate itself in your brain. The Billy Ray Cyrus remix re-contextualized that hook into a proper chorus and unlocked its full power, but the foundation for a monster hit had been there all along.

Andrew Unterberger: I think we underestimated LNX's ingenuity, and just how many cards he had to play to keep the song at the forefront of the conversation. He timed the whole thing beautifully — from the initial Billy Ray Cyrus remix that propelled the already-massive song into the stratosphere, to the song's star-studded video, to the release of debut EP 7, to this newest trot around the track with Young Thug and Mason Ramsey in tow. He spaced them out well enough from one another that it always seemed like there was something new to talk about with "Road," and that's why 15 weeks into its run atop the Hot 100, it still doesn't feel like it's all that tired. 

2. We've lived with Justin Bieber's new Billie Eilish remix for the better part of a week now. What chance do you think it has of giving "Bad Guy" enough of a boost to launch it from No. 2 to No. 1 on next week's chart? 

Trevor Anderson: One thing’s guaranteed: It can’t hurt. “Old Town Road” has certainly departed the chart heavens and returned to the atmosphere, so other songs finally have a shot at taking it down. Even if “Bad Guy” isn’t dominating the competition – it sits at No. 10 on the U.S. Spotify Top 50 today (Tuesday) – the combo platter of the original and remix make it a serious threat to Lil Nas X. “Bad Guy” is now above “Old Town Road” on radio (No. 5 vs. No. 8 on the latest chart) and remixes tend to drive a good sales boost. And I suspect savvy Bieber fans will be keen on returning their king to No. 1 and preserving his current record-tying mark, so they’ll likely consume the song in several ways to boost his chances.

Gab Ginsberg: The good news is that streaming, sales and any airplay of The Biebs’ remix of “Bad Guy” will contribute to Billie’s solo version, certainly giving it a boost. However, Lil Nas X pulled the same trick on Friday, so his remix with Young Thug and Mason Ramsey will also count towards his No. 1 with Billy Ray. Hard to say whether Bieber’s helping hand will be enough.

Carl Lamarre: No chance. Again, you know I think the power of Billy Ray and Lil Nas X is too strong of a duo to oust of the top spot. While Justin's appeal will certainly help "Bad Guy" remain a top-three lock, I do think Post Malone and Young Thug's "Goodbyes" has a chance to stifle their run. Hate it or love it, Posty has a thing for ending streaks. If you remember, he stopped "Bodak Yellow's" mini-run at No. 1 and dethroned the single with "Rockstar". Because of his die-hard fanbase, I think Posty is the dark horse that can still storm his way through "OTR."

Jason Lipshutz: A pretty good one! We’re talking about a pretty enormous hit on its own merit receiving a well-timed boost from one of the most in-demand pop artists on the planet. We’ll see how the showdown between the “Bad Guy” remix and the new “Old Town Road” with Cyrus, Young Thug and Mason Ramsey plays out, but Bieber’s star power should not be discounted here.

Andrew Unterberger: I would've guessed that Bieber's additions to "Bad Guy" would have been novel enough to at least give the song a fighting chance at taking down "Old Town Road" next week. But I'm not sure that it's captured enough of the public imagination to really make that much of a difference — Bieber's slightly ill-fitting verse might ultimately have been too much of a wasted opportunity. Just goes to show that as much as these high-profile remixes might impact a song's chart math, it's still more about art than simple addition. 

3. Of course, Lil Nas X returned fire with his own new OTR remix this week, and has been (jokingly?) teasing still more remixes to come on his Twitter. Is there any potential "Old Town Road" remix guest at this point who you'd still be interested by, or has that well officially run dry? 

Trevor Anderson: Have to say we’re kind of maxed out – I’ll save a mention for Post Malone if he weren’t juggling three singles right now already. Let’s move on to what the people really want to hear, and an automatic 17-week No. 1 in my book, that Gordon Ramsay remix of “Panini.”

Gab Ginsberg: I honestly think the Billy Ray Cyrus version is where the whole thing peaked, and wouldn’t see myself getting too excited about any additional guests. Except for maybe Cardi B, who already appears on Lil Nas X’s EP elsewhere, but I’d still love to see her hop on OTR.

Carl Lamarre: I still think Da Baby would sound great on it. His delivery can fit any track, and he already has a penchant for anything country (See "Walker Texas Ranger"). I do believe Rihanna would inject an extra dose of life to the record if she chose to jump on the track. Think about it. Her fans are dying for some fresh vocals, why not easily notch another No. 1, while still appeasing to her fanbase with new material?

Jason Lipshutz: We’ve had the Cyrus patriarch on “Old Town Road” for months — it’s time for his superstar daughter to ride through. Miley Cyrus makes a ton of sense for one final remix: she’s been active with new music in recent weeks, has been supportive of Lil Nas X and has certainly moseyed around pop, hip-hop and country over the course of her career. If she can’t hop on a remix, however, Ashley O would be a great backup option.

Andrew Unterberger: C'mon, let's put a cap on the Reznorssaince by getting the man himself caterwauling over some extra buzzsawing guitars on the song's chorus. As every Revisionist Western of the past half-century has taken great pains to point out, there's a dark side to the Old Town Road, and Trent's the man to show us where it leads. 

4. "Old Town Road," "Despacito" (Remix), "One Sweet Day" — are there any common threads you see to those three songs? What lessons, if any, can we take away from them being the only three songs in over 60 years of Hot 100 history to spend 15 weeks at No. 1? 

Trevor Anderson: Everyone wins with collaborations! But truly, that seems to be a key thing in these four-month stays. Funny enough, they’re all different types: “One Sweet Day” united two proven powerhouse talents, “Despacito” catalyzed a global superstar to an already-on-its-way hit that reached into an underserved audience in U.S. popular music and “Old Town Road” was the Internet willing on an underdog with help from a sentimental favorite. That's about all I can come up with, but the fact there isn’t a Guaranteed Formula works for me — it’s more fun when it comes out of the blue.

Gab Ginsberg: All three songs are obviously collaborative efforts. OTR was a solo track at first, but truly took off once Billy Ray Cyrus got involved, and we don’t have to rehash what Justin Bieber did for “Despacito.” Then there’s "One Sweet Day," which was a duet from the start. This isn’t to say that dual or even triple star power is a sure bet for a long-reigning No. 1, but man, does it seem like it’s at least required.

Carl Lamarre: I think each record demonstrated how star power could fuel a record if done correctly. Boyz II Men and Mariah were upper-echelon stars in the R&B world in the '90s. Justin Bieber is a star magnet who helped accelerate Latin music on the mainstream circuit with his appearance on "Despacito (Remix)." For "OTR," it was the killer combination of old school meets new blood from two genres coming from the opposite side of the spectrum. When you pair up together, especially on the right track, great things can happen. 

Jason Lipshutz: There’s a unique braiding of sonic DNA and timing going on with all three. “Old Town Road,” “Despacito” and “One Sweet Day” are all special singles that made sense for the world to latch onto, but they also blew up at their different respective moments for a reason. “One Sweet Day” rode the wave of light-R&B balladry on pop radio in the mid-90s; “Despacito” captured a moment in which Latin trap was spilling over into mainstream pop; and “Old Town Road” harnessed meme culture and genre-smashing into the annals of history.

Andrew Unterberger: I think it shows that a song can't just be an undeniable radio favorite or club-killer to reign for 16 weeks — it sorta has to be an event. That's certainly what it was when the two preeminent Hot 100 forces of the first half of the '90s teamed up for "One Sweet Day," and that's what it was when one of the biggest North American pop stars of the '10s cosigned a blossoming Latin pop crossover by singing in Spanish for the first time. "Old Town Road" certainly didn't feel like that at first — a sub-two minute genre hybrid by a relatively unknown rapper — but countless memes, videos, remixes and controversies later, it's absolutely turned out to be one. All of these songs eventually felt strange to discuss as songs, not phenomenons; even though at the end of their chart runs, they were all just great songs, too. 

5. Final predictions time: What total number of weeks does "Old Town Road" notch at No. 1 before finally falling off for good?

Trevor Anderson: 17. 

Gab Ginsberg: 17.

Carl Lamarre: 21. 

Jason Lipshutz: 16. 

Andrew Unterberger: 18. 

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