Welcome to Sleeper Hit Support Group, a column diving into the song currently occupying the bottom spot of the Billboard Hot 100.

In a pop landscape that asks more questions that it answers, I'm setting out to answer three questions about each of these songs: how it got here, if the song is good, and where it's going. In this 100th spot we'll find unlikely ascents, falls from grace, and resurgences of hits from bygone eras.

Today, we're looking at Kenny Chesney's "Carry On" and the country boom that's defining the 2020s.

How did it get here?

The presence of this song on the Hot 100 at all, albiet at the bottom spot, doesn't really have much to do with Chesney himself. Now that we're squarely in the back-half of the 2020s, a lot of critics and culturati are going to try to pin down what the "sound of the 2020s" are. As it pertains to both mainstream and indie music, the answer seems to be country.

Today, Ella Langley's "Choosin' Texas" earned its 12th nonconsecutive week at #1. For the last several months, it's filled in the slot by default when no other powerhouse artist like Taylor Swift or Drake was there to snatch it from her for a week or two.

It's not just Ella Langley, though. Shaboozey tied Lil Nas X for the longest uninterrupted #1 run with "A Bar Song (Tipsy)" a couple years ago, Morgan Wallen has been a chart titan for the past handful of years, and capital P Pop Stars like Sabrina Carpenter and Chappell Roan have made their own country diversions with "Manchild" and "The Giver" respectively. This all comes on top of the alt-country resurgence in the indie world from acts like Wednesday, MJ Lenderman (who until recently was a member of Wednesday), and Waxahatchee.

Kenny Chesney still being able to chart singles at all 30+ years and 21 albums into his career is a feat on its own, but it'd be foolish to not consider the country boom's assistance to his cause.

For the sake of brevity, I won't go too detailed into Chesney's career, so here's the gist of it:

Kenneth Chesney was born into the average southern American life he talks about in his music. Born in raised of the suburbs of Knoxville, Tennessee, Chesney was the son of a schoolteacher father and hairstylist mother. He got his first guitar in high school, teaching himself to play and write songs. While studying advertising at the nearby Eastern Tennessee State University, he recorded a demo tape to sell at gigs he played at local bars and clubs.

After graduating, he moved to Nashville to pursue his music career, eventually earning himself a residency at a honky-tonk bar called The Turf. A couple years later, he was referred to Opryland Music Group executive Troy Tomlinson (now the CEO of Universal Music Publishing Group Nashville), who offered Chesney a publishing contract after his audition.

He released his debut LP In My Wildest Dreams via Capricorn Records, the label responsible for launching the careers of Otis Redding and the Allman brothers. He had to immediately jump ship to Sony (who he'd remain with until 2018) after Capricorn shuttered its country division less than a year after starting it.

For those unfamiliar with Chesney's music, I would best describe it as proto-bro-country. It doesn't quite veer into the territory that the most pandering of his contemporaries do, but the songs' subject matter definitely plants the seeds for what would become post-9/11 "Bro Country." He sings a lot about the summer and drinking some brewskis with your fellas. His highest charting hit, 2009's "Out Last Night," is about exactly what the title suggests with Chesney recounting "hitting on everybody and their mother" and "Jimmy in a fist fight out by the car."

Chesney's most memorable track, 1999's "She Thinks My Tractor's Sexy," truly epitomizes his brand of country. There's not a lot of storytelling, and he often sings about topics so stereotypical to country music that it borders on self-parody.

The sharpest contrast to that pattern, though, was "That's Why I'm Here," his first Hot 100 entry in 1998. The song, much to my surprise, is from the perspective of a man who just checked into rehab and is explaining (as the title implies) why he's there. Again, not for me, but I can't really knock it in good conscience. From looking at the comments under the music video, it's seemed to have helped a lot of people struggling with addiction. "I sober up after playing this song over and over. I begged God to heal me of my own self destruction...and he did. I've sober [sic] for 11 years now. It took alot [sic] of praying, a lot of meetings, and a lot of hard work, but now I'm here . Thank you Jesus and thank you Kenny for such a touching song," one comment reads.

Chesney didn't really get serious in his music again until relatively recently. He started getting vaguely political in the 2010s with songs like "American Kids" and "Get Along." This pivot proved solidly successful for someone two decades into their career, with those songs becoming his most successful on streaming. The latter echoes the centrist "why can't we all get along" sentiment that I hear all the time when visiting my midwestern hometown, so the song's success is wholly unsurprising.

That political pivot didn't carry over into the 2020s, though. Chesney's music since has returned to his regular beers and chicks and trucks programming, and he's fully crossed into legacy act territory by collaborating with the new generation of country stars like Kelsea Ballerini and Megan Moroney. Those features have garnered him his most recent charting hits, until this week.

In an unorthodox move, Chesney changed labels to become the flagship artist of the recently established HEY NOW Records, helmed by three Music Row veterans that were disenchanted with how business was being conducted at the majors. “HEY NOW Records was born out of conversations Clint [Higham], Kenny and I had about the increasing lack of focus that artists are getting as rosters increase while staffs shrink,” co-founder John Esposito shared in a statement. This is a very real and exponentially pertinent issue facing the music industry right now, so if a big ticket artist like this is willing to leave a cushy major-label deal for partners they believe in, that's always something worth applauding.

But with all that said...

Is the song any good?

I can't say I was really expecting anything I would enjoy from Chesney – his music has just never really been for me – but "Carry On" is astonishingly formulaic. It's written in service to get back to the chorus as quick as possible to an extent that feels insulting as a listener. The verses are so short that the chorus feels like a pop-up ad that won't stop duplicating.

In fact, the verses are so far from the song's focus that Chesney makes a Freudian slip about Elvis liking much younger girls. The song starts out describing a 69-year-old bartender, and the second verse implies that she was an Elvis groupie back in the day: "Well, it turns out she kissed Elvis / The story she told would make Penny Lane jealous." Even if these events happened at the end of Elvis' life, the oldest this woman would've been at the time is 19 or 20. Nobody working on this song seemed to have given that detail a second thought, but it's probably the only thing I'll remember about "Carry On" when all is said and done. Also, how dare you bring Penny Lane into this! My culture is not your costume, Kenny Chesney.

Where is it going?

This song? Probably nowhere. Chesney's spot on the chart was carried by country radio support based on his name recognition alone. The country boom, though, is hitting some sort of apex right now. "Choosin' Texas" will probably still be #1 next week, and I'd be shocked if it left the top five anytime soon. On the indie rock side of the equation, Wednesday frontwoman Karly Hartzman just featured on a Weezer song and opened for Bleachers at Madison Square Garden. MJ Lenderman would have opened for Zach Bryan this month had he not dropped the shows to take a much-needed break from touring.

Country's surge in popularity also seems to be catching the eyes and ears of Taylor Swift, who has been conveniently buddying back up with her industry friends in Nashville. Troy Tomlinson, the man who offered Chesney his first publishing deal, was a guest at Swift's wedding this past weekend. Ahead of the release of her rootsy Toy Story 5 end-credits song "I Knew It, I Knew You," Swift took the time to meet with a bunch of country radio programmers. So naturally, the song made history when it became the first song by a woman to have every country radio station reporting to Mediabase sign on to play the song in the first week. In a note shared to the industry trade publication Country Aircheck, Swift wrote, “Man, it’s been a while! Thank you for making history with me. To infinity and beyond.” 

Kenney Chesney has nowhere to really "go" at this point. He's 58 years old, he was inducted into the Country Music Hall of Fame last year, and he was the first country artist to have a residency at the Las Vegas Sphere. He'll be entertaining at amphitheaters and casinos in towns you forgot existed until he croaks or simply doesn't want to anymore. C'est la vie.