It’s hard to pin down just which musicians will stand the test of time. Once they’ve achieved icon status after 40 or 50 years in the biz, it’s nice to take a trip down memory lane to chart a course through their meteoric rises.
However, there are a rare few artists that you can see the iconic moments forming in real-time. Whether it’s a landmark album that seems to shake up the industry as we know it, a colossal show that you can nearly see as the penultimate moment in a biopic, or a record-shattering milestone reached that solidifies them in the annals of music history forever.
One such artist is Harry Styles. From heartthrob boy bander to pop-rock mainstay, Styles is a legend in the making. While his stint in One Direction is iconic in its own right, below we’re sticking to Styles’ solo career, taking a look at just a few top moments from his journey so far.
1. Styles Shares His Self-Titled Debut Album
As One Direction came to a rolling stop (the group softened the break-up blow by announcing a “hiatus,” though the time-out doesn’t seem to be stopping any time soon), each individual member of the group began foraying out on their own, dropping such a vast array of music it’s a wonder they could ever agree on anything at all.
The world waited with particularly bated breath to see what the floppy-haired, Mick Jagger-esque Styles would share for his first solo release. The lead single from his debut ended up being the anthemic, rock-steeped “Sign of the Times.” Drawing on his classic influences—everyone from The Beatles to Rod Stewart—Styles distinguished himself as the breakout star of the group, far outselling his bandmates’ burgeoning solo careers.
2. Christopher Nolan’s Dunkirk
The early days of Styles’ solo career were not only characterized by a solid 10-track album, but also by an expectation-defying role in Christopher Nolan’s Dunkirk.
In particular Nolan fashion, not much was known about the war-time epic prior to its release. Though one notable aspect that audiences began to grasp quite quickly was the addition of a certain ex-boyband member to the cast.
Joining the likes of Tom Hardy, Kenneth Branagh, and Mark Rylance, Styles seemed to fit comfortably in the mix of seasoned actors, quieting the widespread criticism that flew around social media ahead of the film’s release. An unexpected—and pretty ballsy—decision for so early on in his solo career, the role broadened Styles’ appeal even more.
3. Duet With Stevie Nicks on “Landslide”
After years of selling out the world’s biggest stages alongside his One Direction bandmates, Styles opted for a more intimate slew of dates for his debut tour. It seemed Styles wanted to do things in the tradition of an “up-and-coming artist” rather than resting on his stadium-filling laurels.
The dates saw Styles play at iconic venues like The Troubadour in West Hollywood and the Ryman Auditorium in Nashville. In addition to setting the perfect contrasting tone against his 1D days, his new soft-rock sound was validated by Stevie Nicks, who joined the young singer for a rendition of “Landslide.” Their voices melted into one another during the performance as Styles began to take shape as a classic rock star for the new age.
4. Styles Shares Sophomore Album, Fine Line
While his debut album did the trick in defining his personal sound, it was Styles’ sophomore effort that earned him his stripes.
Fine Line took in all the criticism surrounding the classic rock pastiche in his debut, stayed true to what worked, and made a few key adjustments to take things from a gainful imitation to something deeply personal.
Opening with a bang, the buoyant “Golden” drops his second album in a particular place and time—somewhere in Italy perhaps with the sun shining, top down in the fast lane. He treks along steadily across the next few tracks (including singles “Adore You” and “Watermelon Sugar”) before quickly pulling over for some broodier numbers (“Lights Up” and “To Be So Lonely”).
Rich in textures, sonic diversity, and slightly steamier lyrics, the album was a welcomed evolution in the Styles domain—clinching cross-over success into the mainstream that often dismissed him during his boyband days.
5. “Watermelon Sugar”
One major catalyst in his mainstream success was the cheeky fourth single from Fine Line, “Watermelon Sugar.” Though Styles had long been “part of the furniture” by 2019, those that sang his praises tended to be fans who had been doing so since he first shuffled out unto The X Factor stage all those years ago—the rest of the world was taking a while to catch on.
With “Watermelon Sugar,” Styles made waves on popular radio and arguably delivered the song of the summer. All of a sudden, it was more than just stan twitter that was raving about the pop-flavored gem, the entire world was grooving along as Styles sang tastes like strawberries / on a summer evenin’.
6. Love On Tour
To support Fine Line, Styles began to take on slightly bigger stages, embarking on an arena tour that he playfully dubbed Love On Tour.
With a fully fleshed-out band (one that should really be given a name a la Tom Petty and the Heartbreakers, given the integral part they play in the Styles zeitgeist) and a host of matured hits, Styles’ second foray out on the road was something to behold.
Bringing high energy from top to bottom, it was a run of shows that were worthy of such a staggering album.
Styles cemented his place atop the world by headlining Coachella Music Festival. The opening night set saw Styles play through his tour-honed show with some famous cameos and a few sneak peeks of what was to come on his third album.
The festival’s first weekend saw Shania Twain join Styles for a delightfully playful duet of her 1997 hit “Man! I Feel Like a Woman!” before slowing things down for one of Styles’ personal favorites (he also sang it was Kacey Musgraves on his debut tour) “You’re Still The One.”
The second weekend saw Lizzo join Styles for an equally iconic performance of Gloria Gaynor’s “I Will Survive.” The duo, who have long expressed their close friendship, ran around the stage in matching faux fur coats—clearly having the time of their lives.
His appearance at the festival proved that Styles could do more than wow his die-hard fans, he could muster up the energy and stage presence worthy of a festival headliner.
8. Styles Shares Third Album, Harry’s House
To announce his highly-anticipated third album, Harry’s House, Styles did a spread in Better Homes & Gardens—an outlet more so known for peddling the finer aspects of home decor than bolstering the efforts of musicians.
Though at first glance the partnership seems a bit offbeat, after the release of said album, it all began to come into focus—Harry Styles is now a lifestyle influencer.
If Harry Styles was his world premiere and Fine Line was his ticket to the big time (albeit twice over), Harry’s House was a declaration that Styles isn’t afraid to do things his own way. Nearly dropping the soft-rock tones in his earlier work, entirely in favor of modern alternative flavors, Styles isn’t aiming for anything too lofty in his latest album. Instead, he wants to focus on the simple aspects of life—being happily in love, indulging oneself, and taking things slow.
Bold, adventurous, and more referential than his previous work, his third album marks yet another evolution for Styles. A trend that we can only expect to see continue in the future.
9. Styles’ Takes on Stadiums
As stated earlier, Styles and his fellow 1D members are no strangers to stadium shows. From L.A. to Sydney, the five-piece routinely sold-out venues with 70,000-plus capacities. Though Styles probably could have very easily kept that streak going before he even put out his first solo single, Styles decided to ease into things—building his new identity from the ground up.
Whether he feels he’s earned it or it was just the inevitable march of things, Styles has climbed his way to the top for a second time, embarking on an extension of his Love On Tour—this time with stadium dates.
Adding in some selections from Harry’s House, the already colossal tour was revamped to fill up the larger space, proving once again that Styles is a force to be reckoned with.
10. Don’t Worry Darling and My Policeman
After the success of his first film role (along with a little cameo in the end credit scene of Marvel’s Eternals), Styles is slated to appear on the silver screen once again in the impending films Don’t Worry Darling and My Policeman.
The former sees Styles playing opposite Florence Pugh in an eerie drama helmed by director and current girlfriend Olivia Wilde. The initial trailer for the film generated widespread buzz around the project, with Styles appearing to take on a far larger role than he did in the near dialogue-less Dunkirk.
The latter is a period drama with Styles caught between his fiancé (Emma Corrin) and a museum curator (David Dawson), which boasts an equally starring role for Styles.
It’s been five long years since fans got a good look at Styles in action on the big screen. After successfully delivering three lauded albums, it seems Styles is making a bold statement—he’s not afraid to have it all.
(Photo by Dave J Hogan/Getty Images)