7 Iconic Harry Styles Moments!

Many of you have known Harry Styles since his One Direction and X-Factor days, but even as a solo artist, he’s managed to remain as iconic and as amazing as ever. Let’s make our way down the timeline and look back at Harry’s iconic moments as a solo artist.

When He Cut His Luscious Locks

On May 6th, 2016, Harry Styles posted a picture on his Instagram and it was captioned, “Whoops.” In the picture, Harry’s hand is seen holding a ponytail that one can assume was his precious locks. That was the beginning of a new era, the HS1 era.

In Harry’s documentary, Harry Styles: Behind the Album, he showed us how the haircut came to be. It turns out, he had to chop his hair in order to prepare for his role in his first movie, Dunkirk. Although he tried to keep his new hair hidden, fans managed to sneak everyone a peek while he was on the Dunkirk set.

What is even more beautiful about this haircut is that Harry donated it to the Little Princess Trust, which is an organization that provides wigs to children and young people with cancer, and they also provide funding for critical research for pediatric cancer.


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His Duet With Stevie Nicks On “Landslide”

In 2017, while Harry was just starting off his solo career, he was performing in very intimate venues, one being the Troubadour in Los Angeles. The night was made even better when he invited an unannounced guest onto the stage, Stevie Nicks. They performed “Landslide” and “Two Ghosts.”

Harry was starstruck and even stood in the crowd to hear Stevie speak while in-between songs. Their relationship remains very strong because they performed together again in 2019 during Harry’s One Night Only at the Forum for the release of Fine Line. Fans loved it just as much as Harry did, if not more. This is us, manifesting more of Stevie and Harry.

His First No. 1 Hit on the Billboard Hot 100

In 2020, “Watermelon Sugar” became Harry’s first No. 1 on the Hot 100, while his album, Fine Line, was No. 1 on the Billboard 200. “Watermelon Sugar” became the song of the summer in 2020 and remained on the Hot 100 for 39 weeks.

You can often find fans talking about the sweat and tears they put into making sure it went No. 1. We couldn’t be more proud of you, Harry <3

“Bring Back Manly Men”

Harry Styles made history, as he became the first solo male to be on the cover of Vogue in the December 2020 issue. Tyler Mitchell, who became the magazine’s first African American photographer to shoot a cover, shot the cover for Harry.

This photo shoot was loved by Harries, but not Candace Owens. On November 13th, 2020, Owens berated Styles for wearing a dress and said to “bring back manly men.” However, with Harry’s motto being “Treat People With Kindness” his way of responding was, of course, a cheeky Instagram post.


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When He Won His First Grammy Award

In 2021, at the 63rd Annual Grammy Awards, Harry won his very first Grammy for Best Pop Solo Performance for “Watermelon Sugar.” Yep, this was the song that also gave him his very first No.1 single on the Billboard Hot 100. This song did so much for Harry. This also means he became the first former member of One Direction to win a Grammy.

This became a moment of pride for the entire Harry fanbase. When you read the Tweets, they read almost like the Facebook posts your mom may post after you win an award at school.

“As It Was”

On March 31st, 2022, Harry released the smash hit, “As It Was” and it lead as the first single for his most recent album, Harry’s House. Ever since the song was released, it has been a remarkable success for Styles and the music industry. It has been in the Top 15 of the Billboard Hot 100 for a year.

In September of 2022, “As It Was” became “the longest chart-topping run for a British artist, but also the longest-running No. 1 with no accompnaying artists,” with the track spending 15 weeks at the No. 1 spot. The song also received 2023 Grammy nominations for Song of the Year and Record of the Year. It won a 2023 BRIT Award for Song of the Year.

He performed it live for the very first time at Coachella on April 15th, 2022 and fans were freaking out!

15 Consecutive Sold Out Shows at MSG

Harry became the third musical artist to receive a permanent banner in Madison Square Garden for selling out 15 Love On Tour shows at the venue. The residency shows grossed MSG $63.1 million and sold 277,000 tickets. During his time at MSG, the venue really became his house “with specialty foods, exclusive merch, and singae in nearby subway stations.”

On the final show, on September 21st, fans at the show went home with a feather boas and were blessed enough to witness this special moment in person. The presentation of the banner was anchored by Gayle King. Jim Dolan, executive chairman and CEO of MSG Entertainment said “Selling out 15 consecutive nights at Madison Square Garden is a massive accomplishment and reinforces Harry Styles as one of the most impactful artists of his generation.” Very true, Jim. Very true.

About the Author

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Izzy Oropeza

Izzy Oropeza is a Junior at Penn State University majoring in advertising/public relations with a minor in theatre. She is an intern for AfterBuzzTV and Heal Squad with Maria Menounos and she hopes to pursue a career in the entertainment industry, whether on the screen or behind the scenes.