It’s official: Shaboozey‘s “A Bar Song (Tipsy)” spends a 19th week at No. 1 on the Billboard Hot 100 this week, tying the all-time record set by Lil Nas X’s Billy Ray Cyrus-featuring “Old Town Road” in 2019.

The song holds at No. 1 the week the same week that his new single, “Good News,” debuts on the Hot 100 at No. 71. It also follows an eventful night at the CMA Awards for the singer-songwriter, where he performed and was a multi-time nominee, and made headlines at the awards for being the subject of several on-stage jokes that played off his name in a way that some found distasteful.

Will Shaboozey’s new hit be a success in its own right? And will “A Bar Song” eventually rack up a 20th week at No. 1?

1. Shaboozey’s “A Bar Song” has tied the 19-week record at No. 1 on the Hot 100. On a scale from 1-10, how momentous an occasion do you think this is in chart and/or popular music history?

Kyle Denis: 10. This is probably the single grandest Billboard chart achievement; it’s an incredibly momentous occasion. Especially considering Shaboozey did it as a new artist with no high-profile remixes. It does feel a bit muted because 2019 was just five years ago, but few things can truly take away from how insane it is that the two longest-running Hot 100 No. 1 songs of all time are hip-hop-infused country songs by Black men.

Jason Lipshutz: A 10. I am on record writing that I didn’t think “A Bar Song” would get to 19 weeks, because 19 weeks at No. 1 is literally historic, and only one other song and soared that high in the generations-spanning history of the Hot 100. Now that it’s here, “A Bar Song” deserves its flowers, and to sit alongside “Old Town Road” in the pantheon of new-school mega-hits, the type of months-long smashes that we’ll be happily humming many years from now. Shaboozey should savor this moment, but so should all pop-watchers. 

Melinda Newman: I’d give it a 9. Shaboozey had put out two albums prior to the album with “A Bar Song,” and several non-charting singles and now he’s verging on becoming a household name. He already has the record for most weeks at No. 1 for a non-collaboration in the 66-year history of the Hot 100. From here on out, every artist will be chasing his (co-) record.

Jessica Nicholson: 7. Like “Old Town Road” before it, Shaboozey’s “A Bar Song” was an inescapable hit this year, and both were led by Black artists, each crafting their own blend of elements of country, pop and rap into massive hits that resonated with nearly everyone, proving that the amalgam of those genres is a winning formula.

Andrew Unterberger: I’d say an 9. It doesn’t feel quite as momentous as when “Old Town Road” set the record five years ago — mostly because that was only five years ago, and because in the last decade the Hot 100 has clearly started to tilt towards longer-running No. 1s than in prior decades. But a 19-week No. 1 is a 19-week No. 1, and “A Bar Song” was one of the year’s most fascinating singles even before it began its incredible chart run, so it’s definitely still a very, very big deal.

2. Let’s say at Thanksgiving this week, a friend or relative of yours without much frame of reference for pop or country music asks what the deal with this song is. In one sentence, how would you explain this song’s popularity to them? 

Kyle Denis: Country and western sounds and aesthetics have been defining aspects of pop culture this year, and “A Bar Song” captured all that energy into a literal, ridiculously catchy, bar song. 

Jason Lipshutz: “It’s an anthemic, undeniable sing-along that became historically gigantic by appealing to all sorts of fans — country fans, pop fans, hip-hop fans, fans of J-Kwon’s impeccable 2004 jam ‘Tipsy’ — and clicking at every consumption platform that exists, from top 40 radio to TikTok.” That’s a long sentence, but still one sentence.

Melinda Newman: Even though the song is ostensibly about drinking away your troubles, it’s so insanely catchy, that you can’t help but tap your toes and sing along even if you’re nowhere near a bar or have no history with Jack Daniel’s.

Jessica Nicholson: This song blends a weekend barroom party groove, with lyrics steeped in laidback, workweek escapism, all rolled into one.

Andrew Unterberger: Whether you’re a pop fan, a rock fan, a country fan or a hip-hop fan — or best of all, if you’re all four — everyone loves a good barroom singalong.

3. Shaboozey’s “Good News” also debuts on the Hot 100 this week. We won’t ask if it’ll match the very-close-to-unprecedented success of its predecessor, but what kind of chances would you give it of quickly disqualifying Shaboozey from any one-hit wonder considerations? 

Kyle Denis: I’d say it’s still early. It honestly feels unfair to even begin speculating about how a new Shaboozey single will perform as long as it must exist in the domineering shadow of “A Bar Song.” “Good News” doubles-down on Shaboozey’s country framework and shifts away from the uptempo hip-hop nods of “Tipsy,” which might limit just how far it can crossover. Prior to “A Bar Song,” Shaboozey tracks weren’t debuting on the Hot 100 after the first week, so the performance of “Good News” is already promising. And even if this particular song isn’t his second hit, that doesn’t mean he won’t snag one with a different tune. 

Jason Lipshutz: I like “Good News” — it’s essentially “A Bar Song (Mournful),” with an impressive vocal take from Shaboozey and some nifty violin work snaking throughout the production — but I’m not sure it will replicate even a tenth of its predecessor’s success. “Good News” is arriving at a crowded moment at the top of the charts, with enduring hits, a new Kendrick Lamar album and the holiday music onslaught about to start. While I’m not sure Shaboozey’s latest will be able to hold on through January and make a chart push, I feel pretty confident that he’ll have something else in 2025 that can follow up “A Bar Song” and silence the one-hit-wonder chatter.

Melinda Newman: Here’s the “good news”: With “A Bar Song,” Shaboozey has already established himself with an instantly recognizable voice. I heard “Good News” and knew it was him without waiting for the song to be ID’d. Having said that, it’s going to take more than one hit and several years for Shaboozey to escape one-hit wonder status. And no matter how many hits he gets, this will be his signature song, but that’s not such a bad thing. I doubt Garth Brooks complains that fans wait all show to hear “Friends in Low Places.”

Jessica Nicholson: The song is already making strong inroads on the Hot Country Songs chart with a top 20 debut, so it seems very likely that this track will void any potential “one-hit wonder” notions. Like “A Bar Song,” “Good News” incorporates a singalong chorus and rustic-leaning acoustic guitar rhythms, which also lends a bit of familiarity for fans of “A Bar Song.”

Andrew Unterberger: Between its rousing chorus and capo’d acoustic guitar melody — and more than a hint of Zach Bryan on the verses — it certainly feels like it could (and should) find a big fanbase on streaming, radio or both. That doesn’t mean it necessarily will — plenty of prior non-“A Bar Song” Shaboozey songs were worthy singles that ended up not really catching fire — but I like its chances.

4. While this is a triumphant, headline-grabbing moment for Shaboozey, he has also been in the news the past week for last week’s CMA Awards, where he went home empty-handed and had his name used as a punchline in a variety of on-stage jokes. Do you think the CMA stuff taints the moment for Shaboozey, or will it soon become a footnote to his and his song’s historic accomplishments? 

Kyle Denis: It’s a footnote that only reflects poorly on the CMAs. Hopefully, this moment can help crystallize Beyoncé’s true aim of Cowboy Carter – or at least what I think she was trying to get at. Through its expansive envisioning of Western and Americana aesthetics and collaborations with genre-bending artists like Shaboozey, Cowboy Carter found Beyoncé trying to remind us that being “country” and country music are far bigger than the CMAs or Nashville or any other institution. Shaboozey played the game and earned one of the two biggest songs in Billboard history — that still wasn’t enough to receive basic respect at his genre’s biggest awards show. Why continue to grovel for a seat at their table when you could build several dining halls elsewhere in the vast expanse that is country music?

Jason Lipshutz: Definitely a bizarre moment that possibly left a poor taste in Shaboozey’s mouth, but I’d bet every other artist at the CMA Awards would have wanted a 19-week No. 1 smash instead of a trophy that evening. I’d guess that Shaboozey has a good shot at the best new artist Grammy, and “A Bar Song” is one of the favorites for song of the year — possible redemption, although even being blanked at the Grammys won’t diminish the song’s achievement. 

Melinda Newman: Definitely a footnote. He’s already been very classy about the jokes on social media and the simple fact is 80% of the nominees lose, so there’s no shame in going home empty-handed. He gave a fine performance of “Highway/A Bar Song,” and performances are, by and large, what move the sales/streaming needle post-awards show, not whose name is called when the envelope is opened.

Jessica Nicholson: In the short-term, it does feel like it temporarily taints the moment a bit, given all of the big milestones he’s had this year, from being featured on Beyonce’s Cowboy Carter album, his huge CMA Fest performance that shut down Nashville’s Lower Broadway this summer, his Billboard cover, sold-out shows and his Grammy Awards nominations. But in the long run, it will likely be a footnote, given the historic chart run of “A Bar Song,” and Shaboozey’s musical talent, which will likely be giving us more hits in years to come.

Andrew Unterberger: It’s part of his story now, but obviously not as big a part as having one of the two longest-running No. 1 hits in Hot 100 history. You just hope that everyone learns from this moment and Shaboozey is treated more like an insider than an outsider at the next such awards show.

5. The Hot 100 was already about to get crowded with the Christmas rush, and now Shaboozey has a new Kendrick Lamar album to deal with as well. Do you think “A Bar Song” manages to score a record-breaking 20th week at No. 1? 

Kyle Denis It’s possible! Kendrick will probably snag a week or two on top before the holiday songs begin to dominate, so if I were on Team Boozey, I’d keep an eye on January. Release a remix – Maybe J-Kwon gets a call? Tease a Beyoncé version at either of their respective NFL halftime sets? — as the holiday songs begin to fade, but before Kendrick gets a double-whammy of a boost come February with the Grammys (Feb. 2) and the Super Bowl (Feb. 9) in back-to-back weeks. 

Jason Lipshutz: Look, I have been the one saying “No way it gets to 10 weeks,” “No way it gets to 15 weeks,” “No way it gets to 19 weeks.” You know what? I’m calling it: “A Bar Song” gets to 20 weeks, somehow, some way! I am now drinking the whiskey, going to the party downtown near 5th street.

Melinda Newman: Sadly, no. Even though “A Bar Song’s” sales are going up, its streams are slowing, and it seems unlikely to hold off the juggernaut that is Kendrick Lamar, and, most notable, “Squabble Up” from Lamar’s new album. Plus, Christmas songs will start re-entering and soaring back up the chart. But that doesn’t take away from his remarkable accomplishment.

Jessica Nicholson: Even though “A Bar Song (Tipsy)” has had a stellar run, between the chart surge of holiday songs and the buzz around this new Kendrick Lamar album, it seems likely that “A Bar Song” will get overshadowed on the Hot 100.

Andrew Unterberger: Not in 2024, I don’t think. But we’ve likely got a sleepy January ahead, and I bet it can get at least one more week at that point.