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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 June 22), a recently minted new pop superstar has two songs that could take over the top spot next week.  

Sabrina Carpenter, “Please Please Please” & “Espresso” (Island/Republic): Sabrina Carpenter’s set at New York’s Gov Ball music festival on Saturday (June 8) was something of a coronation, as the ascendant pop star played to a headliner’s-worthy crowd in the late afternoon, creating near-hysteria in Flushing Meadows Corona Park with her now-hits-filled set. It helped that she also had a brand-new hit to play live for the first time: the slapping, pleading and unexpectedly twangy “Please Please Please.”  

“Please” was released just the Friday before, along with a buzzy video starring her now-confirmed real-life paramour, Oscar-nominated Saltburn star Barry Keoghan. By the time of her Saturday performance, the song had already gone viral, proving particularly catchy on TikTok for its radio-unfriendly chorus hook “Heartbreak is one thing, my ego’s another/ I beg you don’t embarrass me, motherf—ker.” (Signs held up in the audience read “Please please please play ‘Please Please Please.’”)  

While the song was immediately successful on streaming, Carpenter’s Gov Ball set (which also caught a good deal of online interest) just poured gasoline on the fire — helping the song reach the top of the daily and real-time charts for both Spotify and Apple Music, as its video continued to reign on YouTube’s Trending for Music page. It has only continued to grow on DSPs in the days since, netting over 5 million daily U.S. plays on Spotify as of Tuesday. The song has been less immediately dominant in sales and radio airplay, but has also reached the top 10 on iTunes’ real-time chart, and is starting to get some early curiosity spins on the airwaves, led by SiriusXM’s Hits 1 channel.  

But of course, the bigger the song gets, the more traffic it runs into from her current piping-hot smash: “Espresso,” which slips 5-6 on this week’s Hot 100 (dated June 15), but which is also up across the board following the release of “Please” and Carpenter’s Saturday festival set. On Spotify, the song is No. 2 behind “Please” on its Daily Top Songs USA chart, while rating at No. 5 on Apple Music’s real-time chart. It leads “Please” on iTunes, and obviously it’s way ahead of the new song on the airwaves, having moved into the top 10 on Billboard’s Radio Songs chart for the first time this week. (Incredibly, both songs still trail her Emails I Can’t Send deluxe edition cut “Feather” there, which gently falls to No. 8 on that chart after hitting a No. 5 peak in May.)  

Both “Please” and “Espresso” are likely to populate the Hot 100’s top five this week, and may even have a shot at the No. 1 spot. Their chances should depend on how both songs continue to maintain their post-weekend momentum in the final days of the tracking week – or grow even further – with “Please” likely having the inside track between the two songs based on how stratospheric its streaming numbers have already gotten.  

Post Malone feat. Morgan Wallen, “I Had Some Help” (Mercury/Republic/Big Loud): Speaking of Gov Ball: The Friday headliner was none other than Post Malone, who of course got a massive reception across the board – particularly for his encore performance of his and Wallen’s current four-week Hot 100-topper, “I Had Some Help.” (No Wallen guest appearance, sadly for those in attendance.) The performance did not have the galvanizing effect on streaming that Carpenter’s had – maybe he could’ve used a brand new song, too, as “Help” was the only new song from Post’s long-hyped country pivot to appear in his Friday setlist – but the song still holds at No. 3 on the Spotify and Apple Music charts, and No. 5 on iTunes.  

The key for “Help” maintaining separation from the pair of Carpenter hits is, of course, its still-growing radio dominance. The song holds at No. 5 on Radio Songs this week — up 13% in reach, according to Luminate – and jumps 4-3 on Country Airplay and 14-10 on Pop Airplay. If, as trending, its presence continues to expand on those formats this week, while Carpenter’s hits perhaps have a sort of vote-splitting effect on the airwaves, it would certainly help “Help” in its campaign for an uninterrupted fifth week of Hot 100 ruling.  

IN THE MIX

Shaboozey, “A Bar Song (Tipsy)” (American Dogwood/EMPIRE/Magnolia Music): A little further outside of the pop zeitgeist than Posty or Sabrina, Shaboozey’s solo breakthrough smash just continues to get bigger and bigger. While holding in the top five on Billboard’s Streaming Songs and Digital Song Sales charts, it also leaps 22-16 on Radio Songs, with an unusually prolific presence across formats. Billboard’s charts team reports this week that “A Bar Song (Tipsy)” is the first song to be rising in the top 25 simultaneously on the Country Airplay, Pop Airplay, Adult Pop Airplay and Rhythmic Airplay charts — which have coexisted since 1996. The song should continue to contend in the Hot 100’s top five as it keeps rising at radio, meaning it might never be more than a well-timed remix away from making a serious bid for No. 1.  

Billie Eilish, “Birds of a Feather” (Darkroom/Interscope/ICLG): “Birds” (No. 11, a new high) passed “Lunch” (No. 13, after reaching No. 5) last week for the highest-ranking of Hot 100 hits from Billie Eilish’s new Hit Me Hard and Soft album – and next week, “Birds” could hit the top 10 for the first time, as it continues building on streaming (No. 3 on Spotify, No. 8 on Apple Music). It is also beginning to soar on radio, with 1.3 million all-format impressions June 7-10, on the back of airplay from early leaders including SiriusXM’s TikTok Radio and Hits 1, KMVQ San Francisco, WWWQ Atlanta and WIHT Washington, D.C. 

Chappell Roan, “Good Luck, Babe!” (KRA/Amusement/Island/Republic): Of course, discussion of the overall Gov Ball bump would be incomplete without mention of Chappell Roan, whose headline-grabbing Sunday afternoon set – featuring the singer-songwriter in full Statue of Liberty getup, including green skin paint – has also given her overall catalog a major boost. Leading the way there is newest single “Good Luck, Babe!,” which rises 31-26 on the Hot 100 this week, and should be due for another big jump next frame. Whether or not the song can crack the chart’s top tier may depend on if it can secure further radio support, as “Babe” has yet to make the 50-spot Radio Songs listing, but is getting close – including a No. 31-29 move on Pop Airplay this week.