Harry Styles has had quite the transformation since the early days of his career.
The Brit entered into the spotlight in 2010 after trying out for The X Factor UK. During Styles’ time on the show, creator and judge Simon Cowell paired him with fellow contestants Niall Horan, Liam Payne, Louis Tomlinson and Zayn Malik as the boy band One Direction.
The fivesome’s career quickly took off, and they became household names in the U.K., the U.S. and beyond. Over a five-year period, they released five studio albums — Up All Night, Take Me Home, Midnight Memories, Four and Made in the A.M. — before breaking up in 2016 to pursue solo careers. (Malik quit the group early in 2015 due to stress.)
In June 2016, Styles signed a solo contract with Columbia Records, the same label behind 1D. He released his self-titled debut album 11 months later to critical acclaim, and later embarked on a world tour. His sophomore effort, Fine Line, dropped in December 2019.
In addition to his megasuccessful music career, the Brit Award winner has ventured into TV and film. He made his acting debut in the 2017 movie Dunkirk, and later executive-produced the short-lived CBS sitcom Happy Together. He has also guest-hosted The Late Late Show With James Corden twice and appeared on Saturday Night Live five times.
Styles has made headlines for his relationships too. He infamously had a fling with The Xtra Factor presenter Caroline Flack from late 2011 to early 2012, causing controversy due to their 14-year age difference. He later dated Taylor Swift, Kendall Jenner, Camille Rowe and Olivia Wilde.
The Pleasing founder went on to star in Don’t Worry Darling — directed by Wilde — and My Policeman. He later made a surprise appearance as Thano’s brother, Eros, in a post-credits scene of November 2021’s Eternals.
“Harry as Eros was very much a package deal for me,” director Chloé Zhao gushed over the pop star’s casting during a November 2021 interview with Deadline. “I pitched the idea of Pip the Troll [voiced by Patton Oswalt] and Eros to Kevin [Feige, Marvel Studios president] a while back, and I love the idea of exploring an Eternal who is beyond Titan and who may have influenced Thanos throughout the years the same way Eternals influenced us, earthlings. … I kept tabs on Harry since Dunkirk, I thought he was very interesting. After meeting him I realized he is that character — the same way I cast the rest of my cast. There’s so much of Eros in him.”
Scroll down to see photos of Styles through the years:
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1990s
Styles grew up in the Holmes Chapel area of Cheshire, England, with his parents, Anne Twist and Desmond Styles, and his older sister, Gemma Styles. Anne and Desmond divorced when Harry was 7, and she later remarried Robin Twist, who died from cancer in 2017.
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2010
Styles auditioned for season 7 of The X Factor UK in 2010 with Stevie Wonder’s “Isn’t She Lovely.” He made it to the next round but was subsequently eliminated. Then, Cowell decided to give Styles a second chance and grouped him with Horan, Payne, Tomlinson and Malik to form One Direction. The band almost instantly became an international sensation and finished the singing competition in third place.
2011
One Direction released their debut album, Up All Night, in November 2011. It featured the hits “What Makes You Beautiful” and “One Thing.”
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2012
Styles confirmed via Twitter in January 2012 that he and Flack broke up after three months of dating. “Please know I didn’t ‘dump’ caroline,” he clarified. “This was a mutual decision. She is one of the kindest, sweetest people I know. Please respect that.”
2012
One Direction’s second album, Take Me Home, hit stores in November 2012. It included the singles “Live Like We’re Young” and “Little Things.”
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2013
Swift ended her brief romance with Styles in January 2013. A source told Us Weekly at the time that the former couple “had a fight” after the boy bander “said something he shouldn’t have” during a trip to the British Virgin Islands, prompting Swift to fly home to Nashville.
2013
One Direction released their third album, Midnight Memories, in November 2013. Its singles included “Best Song Over,” “Story of My Life” and “You & I.”
2014
The group dropped their aptly titled fourth album, Four, in November 2014. It featured the hits “Steal My Girl” and “Night Changes.” It was their last release with Malik.
2015
One Direction’s fifth and final album, Made in the A.M., was released in November 2015. The singles were “Drag Me Down,” “Perfect” and “History.”
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2015
Styles and Jenner, who were first linked in late 2013, made headlines in December 2015 when they were photographed all over each other on a yacht in St. Bart’s. Four years later, a source told Us exclusively that the pair remain “great friends.”
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2016
Us broke the news in January 2016 that One Direction’s planned hiatus was actually a permanent split.
2017
Styles released his self-titled debut solo album in May 2017. It featured the fan favorites “Sign of the Times,” “Two Ghosts” and “Kiwi,” and Us named it the best album of the year.
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2017
Styles made his acting debut in Christopher Nolan’s Dunkirk, which hit theaters in July 2017 and also starred Fionn Whitehead. The movie was nominated for eight Oscars and won Best Sound Editing, Best Sound Mixing and Best Film Editing.
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2017
Styles kicked off Harry Styles: Live on Tour in September 2017 in San Francisco. He toured North America, Europe, Asia, Australia, New Zealand and Latin America before wrapping up in Inglewood, California, in July 2018.
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2018
Styles and Rowe broke up in July 2018 after quietly dating for one year. He included a voicemail of the model speaking her native French on his song “Cherry” the following year.
2019
The entertainer dropped his second album, Fine Line, in December 2019, featuring the singles “Lights Up,” “Watermelon Sugar” and “Adore You.” Us named it the No. 6 album of the year.
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2021
Styles was photographed holding hands with Olivia Wilde in January 2021 while attending his manager Jeffrey Azoff’s wedding in Montecito, California. The actress directed the “Treat People With Kindness” crooner in the movie Don’t Worry Darling, which they began filming in October 2020. A source later exclusively told Us that the new couple “had chemistry almost instantaneously on set,” while a second insider denied rumors that Styles broke up Wilde’s engagement with ex Jason Sudeikis, with whom she shares son Otis and daughter Daisy.
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2021
Styles won his first Grammy in February 2021 for Best Pop Solo Performance for “Watermelon Sugar,” which he performed at the top of the awards show.
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2022
Styles’ Eternals costar Gemma Chan shared a behind-the-scenes snap of the pair wearing their superhero costumes.
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May 2022
He promoted his third album, Harry’s House, on TODAY’s Summer Concert Series in New York City while rocking neon stripes.
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June 2022
The “Music for a Sushi Restaurant” singer performed in a black and white jumpsuit at Capital’s Summertime Ball in London.
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September 2022
Styles suited up in a blue Gucci number for the Don’t Worry Darling movie premiere at the 79th Venice International Film Festival in Italy.
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February 2023
The “Fine Line” crooner won big at the 65th Annual Grammy Awards, taking home the trophies for Best Pop Vocal Album and Album of the Year for Harry’s House. “I think on nights like tonight it’s so important for us to remember that there is no such thing as best in music,” the My Policeman actor said while accepting his Album of the Year award, which was widely expected to go to Beyoncé for Renaissance. “I don’t think any of us sit in the studio making decisions based on what is going to get us one of these. This is really, really kind. I’m so, so grateful. This doesn’t happen to people like me very often. This is so, so nice. Thank you very, very much.”
