Harry Styles in 10 Songs

A crash course before we enter Harry's House

Harry Styles in 10 Songs
Harr Styles, photo by Lillie Eiger/Illustration by Steven Fiche

    Ever felt intimidated by a musician’s extensive back catalog? Been trying to get into a band, but you just don’t know where to begin? In 10 Songs is here to help, providing a clearcut entry point into the daunting discographies of iconic artists of all genres. This is your first step toward fandom — now all you have to do is take it.

    There just aren’t that many entertainers like Harry Styles these days.

    Harry is more than a pop hitmaker, and even more than the modern iteration of the charming, British rock star. He’s also more than a fashion provocateur, someone who regularly makes headlines for fairly gentle pushes against social boundaries and norms.

    The thing about Harry Styles is that he’s a true renaissance man, the sort that used to exist in the era of Old Hollywood and just beyond, when someone like Frank Sinatra could be one of the best-selling artists of the time while also moving hordes of tickets at the Main Street cinema. Pop stars these days aren’t called to appear in films, tour the country, jump in for a stint hosting a late night show, co-chair a fashion gala, appear on a sketch comedy program, and then head back to the studio — and no one called upon Harry Styles to do so, either. He took it upon himself.


    What’s so refreshing about Styles is that he genuinely seems to love learning about the work of being an entertainer, and does things because he wants to do them. It’s sometimes hard to believe that the nervous kid who auditioned for The X Factor and was tossed into One Direction has gone on to hone strengths in so many different areas, but Harry has also always had that indescribable It factor.

    Some fans expressed mixed feelings about his budding career on the silver screen — that trailer for Don’t Worry, Darling is truly something — but Harry put any fears of moving into acting full-time to rest by confirming a third album, Harry’s House, which arrives this coming Friday, May 20th.

    In preparation for Styles’ third solo effort, we’ve rounded up ten songs that speak to his story so far. Granted, they’re not the definitive top 10, nor are they the only 10 songs that paint a picture of his many strengths. What these 10 songs do demonstrate, though, is that Harry Styles isn’t afraid to try new things, and, more often than not, he ends up being great at them.


    Here’s Harry Styles in 10 songs, featuring a playlist at the bottom for you to enjoy as you read along.

    — Mary Siroky
    Contributing Editor

    Going One Direction (Up): “Olivia”

    It’s indisputable that One Direction was one of the biggest and most successful boy bands of all time. It was also, undoubtedly, a difficult time for the five young men, coming of age as they tumbled into almost overnight success following their time on The X Factor. While One Direction didn’t always offer space for Harry and his bandmates to authentically express themselves or explore their individual tastes, he seems to still have a soft spot for a deep cut beloved by Directioners to this day.

    Current relationship status aside, “Olivia” is a song that Harry Styles included in the pre-show playlist while touring his self-titled solo debut, as well as LOVE ON TOUR, which celebrated his Grammy-winning Fine Line. The truth is that we wouldn’t have the Harry Styles we have today, a full-fledged rockstar, without his roots in One Direction, and it’s nice to see that there’s parts of that time in his life, like this track, that he is able to remember fondly. — M.S.

    His Solo Arrival: “Sign of the Times”

    Just under four years after their smash debut single “What Makes You Beautiful,” and about a year after Zayn Malik left the group, One Direction formally announced their hiatus. While the boy band was careful never to use the harsh language of “breakup,” and dedicated fans continue to theorize about the band’s resurrection to this day, even just a year out from the announcement, things seemed pretty final.


    Malik, having a head start, had already begun establishing his solo presence with the edgy “PILLOWTALK.” Niall Horan quickly followed, contrasting Malik’s synth-pop with the singer-songwriter aesthetics of “This Town.” Louis Tomlinson took to collaborating with Steve Aoki, and Liam Payne would be the last to the party with his Quavo-featured “Strip That Down.” Arriving in April 2017, though, Styles’ first foray into solo artistry would prove to be distinct from his former bandmate’s efforts, telling of his previously unrealized interests, and the most lasting debut of any of them.

    “Sign of the Times” introduced Styles as a poppy classic rock revivalist in the spirit of (as you might have guessed from the name) Prince and early Bowie. A dramatic, building ballad, the track cemented Styles’ prowess as a performer and established him as a respected songwriting force. Even as he continued on his ascent to pop royalty, “Sign of the Times” remained an essential cut in his discography. The song silenced skeptics and reassured fans that Styles’ moment was far from over. It’s hard to imagine a more impactful hello. — Jonah Krueger

    The Essential B-Side: “Kiwi”

    While “Sign of the Times” officially kicked off Harry’s solo era, “Kiwi” immediately became the track to know when Harry Styles was released in full. The Brit-rock pop song is a scorcher, all sly digs at a chaotic lover, big drum fills, and hard-edged electric guitar, and it became even more essential to the Harry Styles Brand once he began performing it on tour.


    Famously, Styles even performed the high-energy song three times in a row in 2018 at the Los Angeles tour stop, which happened to be the closing night of the tour. He didn’t want to leave the stage, so he just kept going, and going, and going — and who would possibly complain about that? Within his discography, now on the precipice of growing with the arrival of a third album, there are quite a few treasured, expertly-crafted b-side tracks. “Kiwi,” though, is the most important. — M.S.

    Our Little Secret: “Medicine”

    Maybe someday Harry will share a studio version of his treasured track “Medicine.” It’s taken on almost mythological status in the Harry Styles canon — Styles is relatively tight-lipped when it comes to labeling his sexuality, preferring to express himself through his art. “Medicine” is the most explicit way he’s ever addressed questions his listeners might have.

    “Take my medicine/ Treat you like a gentleman,” he sings towards the opening of the song, but things really kick into gear in the second verse: “The boys and the girls are in/ I mess around with them/ And I’m okay with it.” (So are we, Mr. Styles.) The song is raunchy, it’s playful, and it’s just plain sexy. He might as well have just sent a video of him performing this live, along with the rapturous reactions, as his audition tape for the seductive MCU role of Eros. — M.S.


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