The Contenders is a midweek column that looks at artists aiming for the top of the Billboard charts, and the strategies behind their efforts. Next week (for the upcoming Billboard Hot 100 dated May 11), Taylor Swift’s second week for The Tortured Poets Department should be less Hot 100-dominant than the first, allowing room for challengers from some much-less established stars (and one of her Eras Tour openers).  

Taylor Swift feat. Post Malone, “Fortnight” (Republic): Taylor Swift of course sets a record this week on the chart dated May 4 by locking down all 14 of the Hot 100’s top 14 spots with songs from her blockbuster new album The Tortured Poets Department, led by the Post Malone-featuring album opener and lead single, “Fortnight.” That song drew over 76 million official U.S. streams in its first week, according to Luminate – the best single-week mark for a song since YouTube user-generated content was removed from chart calculations in 2020 – while also bowing as the week’s top-selling track with 19,000 sold, and entering Radio Songs at a lofty No. 14 with its 31.1 million radio airplay audience impressions. 

The streams and sales should both drop considerably in the song’s second week – as is typical for debuts of its size – but radio should only continue to heat up from here, with the song already challenging for a top 10 spot on next week’s Pop Airplay chart. And while the streams will be down, they should still be fairly mighty in number, as the song remains in the top five on both Spotify’s and Apple Music’s daily US charts and its official music video in the top five on YouTube’s Trending music chart.  

Sabrina Carpenter, “Espresso” (Island/Republic): Swift’s primary competition for the chart’s top spot next week may come from her good friend and international Eras Tour dates opener Sabrina Carpenter. The multi-platform star’s new single “Espresso” became easily her highest-charting single on the Hot 100 with its No. 7 debut last week, and though it slides to No. 22 on this week’s chart, it remains the sixth-highest non-Swift song on the listing.  

“Espresso” should be due for an enormous rebound on this week’s chart, as it continues to grow across the board (and some of Swift’s Tortured Poets tracks vacate the premises). It’s taken over the top spot on Spotify’s Daily Top Songs USA chart from “Fortnight,” and is currently scaling the Pop Airplay chart, bounding 32-25 there in its second frame. One of the only things holding it back is the fact that it’s competing on the airwaves with another of her recent hits: “Feather,” which is still hanging in the Hot 100’s top 50, and hits a new peak of No. 5 on this week’s Radio Songs chart.  

Shaboozey, “A Bar Song (Tipsy)” (American Dogwood/EMPIRE): As Beyoncé’s Cowboy Carter continues to reel in the accolades, its widespread influence on pop culture is already undeniable. Perhaps the most obvious and immediate impact it has had is in the breakthrough success of country artist Shaboozey, who was a collaborator on two of the chart-topping album’s tracks and who just weeks later is already enjoying a crossover hit growing to near-”Texas Hold ‘Em” size, with the celebratory (if slightly melancholy) “A Bar Song (Tipsy).”  

The breakout hit, which interpolates chorus and verse hooks from J-Kwon’s 2004 pop-rap classic “Tipsy,” is one of the only climbers on this week’s Swift-stuffed Hot 100, rising 36-27 on the chart despite the 20 Tortured Poets songs debuting above it. With the song still soaring on streaming – now top five on both Spotify’s and Apple Music’s daily U.S. charts — while also leading on the iTunes real-time chart and beginning to get a foothold in country radio (as it hits No. 1 on the multimetric Hot Country Songs chart), it should be a contender on the Hot 100 for weeks to come, perhaps even challenging the No. 2 peak for the original “Tipsy” 20 years ago.  

Tommy Richman, “Million Dollar Baby” (Pulse/ISO Supermacy): Virginia singer-rapper Tommy Richman first came to public prominence as the signee of (and opening act for) R&B hitmaker and fellow DMV native Brent Faiyaz. Now, he’s on track to score a crossover hit beyond any Faiyaz has yet enjoyed, with the TikTok-teased “Million Dollar Baby.” Released on Friday (April 26), the song has already reached the apex of Apple Music’s real-time chart, and its virality seems to only really be getting started – likely leading to a debut in the Hot 100’s top 10, and possibly the top five if it continues its early momentum.  

Benson Boone, “Beautiful Things” (Night Street/Warner): Can’t count out Benson Boone, whose “Beautiful Things” has been in the mix for the spot for the last couple months now, and who only now seems to be finally peaking at radio, reaching No. 2 at Radio Songs and threatening to end Teddy Swims’ three-week reign on top. It might not be enough to unseat Swift and hold off all her many rising challengers, but ”Beautiful Things” is the highest-ranking non-Swift song on this week’s chart, so who knows? With a little late bump, maybe it could eclipse its prior No. 2 peak and finally get all the way to the Hot 100’s mountaintop.  

Kendrick Lamar, “Euphoria” (pgLang/Interscope/ICLG): The big wild card on next week’s Hot 100 is of course Kendrick Lamar’s Drake response track “Euphoria,” which had a world-stopping debut on YouTube on Tuesday (April 30), and very quickly became what feels like the only song in the world that people are talking about. It arrived on other DSPs and online retailers later in the day, so it should have two full days of tracking along with a partial Tuesday to make up its incomplete first week of chart eligibility – not likely enough to fight for No. 1 in a crowded field, but certainly enough for a splash debut. We’ll see in the weeks to come whether it can follow Lamar’s Future and Metro Boomin collab “Like That” to pole position, and become the rapper’s second Drake-dissing Hot 100-topper of 2024.