New Hits From Tommy Richman, Shaboozey & Sabrina Carpenter Are Scaling the Hot 100 — Which Has the Best Chance to Hit No. 1?

As Taylor Swift rules the Billboard Hot 100 for a second frame with her Post Malone collab “Fortnight” — and before an onslaught of tracks resulting from the culture-dominating Kendrick Lamar/Drake feud likely swarms the top tier of the chart next week — a trio of newer hitmakers move into the chart’s top five.

This week’s Hot 100 (dated May 11) features a debut from Virginia singer-rapper Tommy Richman at No. 2 (“Million Dollar Baby”), along with a rapidly rising breakout smash from country singer-songwriter Shaboozey at No. 3 (“A Bar Song (Tipsy)”) and the biggest crossover hit yet for burgeoning pop star Sabrina Carpenter at No. 4 (“Espresso”). Along with enduring top 10 hits from newly minted hitmakers Benson Boone (“Beautiful Things,” No. 5) and Teddy Swims (“Lose Control”), this week marks the highest concentration of first-timers in the chart’s top 10 since June 2022.

Which one is most likely to claim the top spot in the weeks to come? And is it meaningful to be getting so many big hits by newer artists at once? Billboard staffers discuss these questions and more below.

1. Despite being each artist’s first visit to the chart’s top 10, within a month of their Hot 100 debuts, each of Tommy Richman’s “Million Dollar Baby,” Shaboozey’s “A Bar Song (Tipsy)” and Sabrina Carpenter’s “Espresso” finds itself in this week’s top five. Which of the three hits has been most impressive to you with its rapid rise?

Rania Aniftos: Shaboozey! Black artists are slowly but surely staking their claim in country music and country-adjacent genres, and it’s been long overdue. I’m so glad Shaboozey had his time to shine on Beyoncé’s Cowboy Carter, and has since been able to amplify his own career. I’m impressed by his skyrocketed success and excited to see where he goes from here!

Kyle Denis: Definitely Tommy Richman’s “Million Dollar Baby.” You can track both Shaboozey’s (two Queen Bey collabs + each of previous singles was bigger than the last) and Sabrina’s (Eras Tour opener who has recently solidified herself as a formidable presence on top 40 radio) success pretty easily. Outside of some significant underground motion, Tommy Richman’s name didn’t even exist in the zeitgeist last month – now he has the most-streamed song in the country this week with his very first Hot 100 entry. 

Josh Glicksman: Shaboozey. Parlaying guest turns on a blockbuster album into solo chart success is a much more difficult task than he’s made it seem, and particularly so given that country music typically doesn’t have the immediate streaming power — save for a handful of marquee artists — as some of the other genres filling the top 10 of the Hot 100. Sure, the J-Kwon “Tipsy” interpolation gives “A Bar Song” a boost, but the latter is unquestionably a hit in its own right, avoiding the over-reliance on nostalgia that songs of a similar ilk have fallen victim to in the past year.

Jason Lipshutz: While Sabrina Carpenter has already enjoyed pop radio success prior to “Espresso” and Shaboozey’s profile grew significantly thanks to his multiple features on Beyoncé’s Cowboy Carter, Tommy Richman’s “Million Dollar Baby” has seemingly come out of nowhere to thus far out-chart both of them. Yes, Brent Faiyaz has co-signed Richman and brought him on tour — but Faiyaz has yet to score a solo hit within the same stratosphere as “Million Dollar Baby,” which exploded on TikTok to such a degree that it debuted at No. 2 amidst stiff competition. We’ll see how durable of a hit “Million Dollar Baby” proves to be, but that start was breathtaking.

Andrew Unterberger: All three are undoubtedly impressive, but the real jaw-dropper to me here is Richman. To drop a new single at very possibly the most crowded moment for major new releases we’ve had so far this decade and not only make a major impression, but immediately zoom to the very head of the class — outside of the reigning valedictorian, anyway — is simply stunning for any artist, especially one with so little established chart history.

2. All three songs figure to be contenders for the top spot in the weeks to come. If you had to bet on one of them to eventually get there — or to be the first to get there, if you think multiple will — which would you opt for?

Rania Aniftos: I have to say “Espresso,” because I know I’m not the only one who can’t get that damn “I’m working late/ ‘Cause I’m a singerrrrrrr” line out of their head. It’s such a catchy song and it’s everywhere! 

Kyle Denis: Given that just three 2024 releases have spent more than a single week atop the Hot 100, I’m willing to wager that all three songs will get there – but they likely won’t enjoy very long stays at the pole position. Who’s getting there first? Probably “Million Dollar Baby,” it’s outpacing the other two songs on most major U.S. streaming platforms – and it feels like that kind of hit that won’t necessarily need radio to carry it. 

Josh Glicksman: “Espresso.” Its nu-disco production is tailor-made for sunny days and open windows and will garner endless airplay at pop radio. I expect both “A Bar Song (Tipsy)” and “Million Dollar Baby” to hang around for extended stays as well — and could very well see the former getting to No. 1 as well at some point — but it’s hard to bet against the bona fide pop hit, especially when it’s such an instantly obvious song of the summer contender. Did I already mention how much you’re going to hear it on the radio?

Jason Lipshutz: “Espresso,” since it sounds like one of the sturdiest pop hits of the year, it’s already a top 5 hit, and its radio run hasn’t even kicked off in earnest yet. Songs like “Nonsense” and “Feather” proved Sabrina Carpenter’s top 40 appeal, and “Espresso” is already a bigger hit than both of those previous singles; meanwhile, Carpenter is a more of a prominent star than she’s ever been, and she’s poured us a three-minute shot of bliss in time for summer. The top of the Hot 100 is crowded right now, but I think that “Espresso” will spend multiple weeks at No. 1 in the June/July range.

Andrew Unterberger: I would say “Million Dollar Baby,” since its initial velocity has been so impressive and it’s already so close to the top spot. But the fact of the matter is that it’s likely going to get stuck behind an onslaught of Kendrick Lamar for at least the next week or two, after which another new song (maybe something from the new Billie Eilish album due Friday after next?) very well may have lapped it momentum-wise. So I’ll bet on the long game with “Espresso,” as the song’s warm-weather vibes and Carpenter’s recently established history on the airwaves all but guarantees it ruling radio all summer — meaning it’ll always be in range of the Hot 100’s top spot, and able to seize it with a new remix or video or other viral moment (or if we ever just get another slow chart week again).

3. Beyond these already-minted hits, which of the artists behind them (between Richman, Shaboozey and Carpenter) do you expect to make the biggest/most extended chart impact in the years to come?

Rania Aniftos: Again, I’m going to give this one to Sabrina. She’s been working hard at her career since she was a child on the Disney Channel and I’m surprised it’s taken her this long to pop off. She has an excellent discography and Emails I Can’t Send is a completely underrated pop album. I’m expecting “Espresso” to lead music lovers to finally give Sabrina the success she deserves.

Kyle Denis: My money’s on Sabrina given she already has bigger chart hits than both Shaboozey and Richman. Couple that with the fact that she’s truly made the best of the once-in-a-lifetime opportunity that is opening for what will likely go down as the biggest tour of all time, Sabrina will be around for a minute. At the very least, she’ll become a true pop radio staple. Shaboozey’s path is obviously a bit different as he’s navigating the Nashville machine as a Black man, and Richman will probably collect one or two smaller hits before comfortably reassuming his cult hero status. 

Josh Glicksman: I’ll take Sabrina Carpenter here. She’s been bubbling just under the surface of A-list pop star for what feels like years now (it’s not too late to give “Sue Me” the full moment that it has always deserved!) and now that she’s collecting a handful of Hot 100 entries, I expect that to quickly grow into the size of an overdue grocery shopping list before long.

Jason Lipshutz: Carpenter, whose 2022 album Emails I Can’t Send contained a ton of promise, and everything she’s done since then has fulfilled that promise. “Espresso” represents a breakthrough hit, but Carpenter contains the personality and pop know-how of a superstar — and she’s becoming one now, after years of build-up and gathering momentum. Shaboozey and Richman are both on upward trajectories, but Carpenter has a higher ceiling, and should be a chart force for a long time.

Andrew Unterberger: It’s Carpenter, simply because this moment is the culmination of a good half-decade — arguably even longer — of work she’s put in building her audience and pop cred, and now officially joining the ranks of the A-listers. But honestly, I’m buying stock in all three of these artists. I’d be pretty surprised if this was the last we heard from any of them on the Hot 100.

4. While these are the three biggest breakout hits currently challenging Taylor Swift’s “Fortnight” for the chart’s top spot, they’re hardly the only new singles currently making waves on the chart. Who that’s a little lower down on the listing could you see elbowing your way into the top tier before long?

Rania Aniftos: I feel like Chappell Roan is on a similar wavelength with the artist we’ve been discussing today. “Good Luck, Babe!” is a great track and Chappell is a great artist. I would love to see a snippet from that song go viral and project the track into the top 10. 

Kyle Denis: I’m definitely keeping an eye on Lay Bankz’s “Tell Ur Girlfriend” (No. 58), GloRilla & Megan Thee Stallion’s “Wanna Be” (No. 34, this week) and Bryson Tiller’s “Ciao,” which does not currently rank on the Hot 100. 

Josh Glicksman: Aside from the obvious picks in the Kendrick Lamar-Drake rap battle, Chappell Roan’s “Good Luck, Babe!” and Dasha’s “Austin” both feel like they have plenty of runway left and may jetset well into the summer. The former act is coming into a superstar moment of sorts of her own, while the latter hit continues to build on a global scale. Both currently sit in the 40s, and as the Taylor Swift takeover clears out a bit in the coming week, there should be ample room to grow.

Jason Lipshutz: Chappell Roan’s “Good Luck, Babe!” hasn’t entered the top 40 yet, but the single sounds like a smart, charismatic commercial breakthrough for an artist with a dedicated fan base that’s been growing exponentially over the past few months. I’d expect it to keep climbing in the coming weeks based on its promising streaming returns, and depending on radio’s reaction, challenge for the top 20 (at least) soon enough.

Andrew Unterberger: All signs are clearly pointing to Chappell Roan being next up — though I’m still hoping Nashville stops messing around and finally embraces Dasha’s viral “Austin” as the future of pop-leaning country, which it almost certainly is and should be.

5. Along with Benson Boone’s “Beautiful Things” and Teddy Swims’ “Lose Control,” first-timer artists in the top 10 take up five of the top six spots this week. Do you think it’s meaningful that there has been such a presence for breakout artists in the chart’s top tier this year, or is it just a fluke of timing?

Rania Aniftos: While my gut is telling me it’s a fluke while we wait for the slew of major artist releases this year, I really hope it’s not. It’s been so refreshing seeing new names on the Hot 100, and I want to see more! 

Kyle Denis: I think we’re still in a weird place where pop culture is trying to move forward, but our near-constant nostalgia loop is keeping us beholden to stars of yesteryear. Of course, some of those stars genuinely are still cranking out releases that do meaningfully shift the culture: We’ve gotten back-to-back blockbuster albums from Beyoncé, Ye & Ty Dolla $ign, Ariana Grande, Taylor Swift, and Future & Metro Boomin (twice!) Yet tracks from those albums — barring most of their lead singles — aren’t the ones setting up shop in the Hot 100’s upper regions this year. 

Josh Glicksman: If anything, it’s especially meaningful given the deluge of superstar releases so far in 2024. It could be that there have been so many blockbuster albums that the A-listers are canceling one another’s opportunities for extended chart runs a bit, but regardless, the hits from breakout artists this year are well beyond the point of calling it a fluke.

Jason Lipshutz: The timing is a little fluky — in recent weeks, veteran stars like Beyoncé, Future & Metro Boomin, Ariana Grande and Jack Harlow also occupied the top 10 — but this happy upswing in newcomers to the top 10 also underscores a general hunger for unfamiliar voices in heavy rotation after a run of high-profile albums. The release calendar has been packed so far in 2024, but thanks to a mix of TikTok virality, new pop trends like the country-folk revival, and undeniable singles from non-superstars, the top of the Hot 100 looks revitalized. We’re in for a fun-as-hell summer slate, as big projects and out-of-nowhere hits balance each other out on the Hot 100.

Andrew Unterberger: I think it’s simple: Popular music is up right now. Pretty much all genres, from pop to rap to country to rock, are hitting right now — while also intertwining inextricably, of course — and there’s plenty of room for exciting new releases from both the ruling class of hitmakers and an entirely new wave. It’s a fun time to be a top 40 fan, which is not something we’ve often said this decade around this time of the year.