By Amanda Gilchrist | 1 February 2023
(29) Satellite Stomps
For the Satellite girlies, Harry’s performance of this track is top-tier. But even more, his decision to stomp on every beat during the bridge has inspired a new trend of buying Adidas Gazelles. There will always be a piece of him in the way harries dress.
As Harry’s first film credit, Dunkirk left the fandom speechless. His willingness to transition into new terrain shows his versatility as an artist and foreshadowed the wide breadth of acting credits he would accumulate a few years later.
Does Harry have 3 major Hollywood movie credits to his name? Yes. But how could we forget about his acting debut in iCarly circa 2012.
(26) The Whale
Going back to the One Direction days, I would argue the whale has created some of the most iconic pictures of Harry. I’m still waiting for the day that I learn how to successfully execute this concert staple.
(25) Viva la Vida Shoulder Hits
In One Direction’s debut performance on the X Factor, the recently created band certainly cemented themselves as a fan favorite with the performance of Viva la Vida. A standout moment for fans to this day is Harry’s shoulder pumps on the beat, a dance move still referenced at Love on Tour shows to this day.
Each installment of Harryween seemed to imprint themselves in the record books for their own reasons and I simply just can’t pick one to highlight on this list. From Dorothy and Somewhere Over the Rainbow to the clown and the Medicine - Toxic mashup in 2021 and 2022’s Danny Zuko and cover of Hopelessly Devoted to You, each time Harry hits the stage for Halloweekend fans are sure in for a surprise.
(23) His Collaboration with Gucci
Years after the iconic black and white floral Gucci suit on the 2015 AMA red carpet, things really came full circle when Harry launched his HA HA HA collection with Gucci in June of 2022. A true fashion icon.
(22) Falling at OTRA San Diego
We’ve all seen the video, one second he’s walking along with his mic stand during Through the Dark, the next he’s stumbling down onto the stage. This fall spurred the iconic line “Physically, I’m fine. Emotionally, I’m bruised.” What a way to start the North American leg of OTRA.
(21) Rolling Stone Interviews
Whenever Harry graces the cover of a magazine it is sure to be an item often difficult to acquire. From Vogue to Dazed and Beauty Papers, each shoot and interview for a magazine cover has its own theme, energy and story. But I can tell you the Rolling Stone covers for each album cycle are always some of the best. There always seems to be a raw and honest element that accompanies these interviews and I can’t imagine a new Harry album without one.
(20) Teenage Dirtbag Punches
I’ll tell you what, the edit of the Teenage Dirtbag punches in This is Us has lived rent free in my head for the last decade. I stand by the fact that 2013 Frat Boy Harry singing this song on the Take Me Home tour is certainly a core memory of my childhood and the punches in the bridge are a huge part of that.
(19) The OG MSG Arms Instagram Post
I don’t know about you, but I know I anxiously await the updated Madison Square Garden arms photo every time Harry plays in New York. The Instagram post tradition that started in 2012 when One Direction played to a sold out crowd at the Garden served as the starting point for years to come. Looking at the updated pictures side by side sure is a good way to reflect on Harry’s amazing career.
(18) His Golf Dad Count
A staple of the New York residency shows, the “Golf Dad Count” is one of my favorite parts of the 2022 Love on Tour shows and was always a ure fire way to get the crowd going.
(17) Winning a Grammy for Best Pop Solo Performance
Harry’s first ever Grammy was so well deserved and all I can say is that I cannot wait to see if he brings home another one this weekend.
(16) Launch of Pleasing
Harry truly is a man of many talents. In November of 2021 he launched his beauty and skincare brand Pleasing which continues to churn out stunning nail polishes and apparel items with each new collection.
(15) Met Gala
The Met Gala is a classic fashion event and Harry is a fashion icon! One of his first debuts in the fashion world, Harry had his fans in a chokehold with his pearl earring and sheer-back blouse.
(14) Hosting SNL
Over the years, Harry has made many performances and appearances on shows, but perhaps his most iconic is when he hosted SNL. With references to his time in One Direction and referring to Zayn as “Ringo” in his monologue, his performances on SNL never disappoint.
(13) Memorial to Throwing Up on the Side of the Road
This is a true One Direction classic, but since it directly involves Harry it has to be included on this list. Poor Harry needed a brief moment off the 101 Highway in Los Angeles after allegedly “completing a very strenuous hike”. Yeah right, Harry!
(12) His X Factor Audition
It really wouldn’t be a full countdown of Harry’s best if we didn’t commemorate the start. I can’t be the only one who still gets nostalgic over clips of the curly headed 16 year old with the whole world ahead of him. But let’s just stick to remembering the rendition of Isn’t She Lovely instead of Hey, Soul Sister.
(11) Stevie Nicks at the Troubadour
It’s no secret that Stevie Nicks is one of Harry’s biggest influences. Even after performing with her multiple times, I still think the best one is their performance of Landslide at the Troubadour in 2017. The look on his face says it all and that performance is one that brings me to tears to this day.
(10) Helping His Fans Come Out
On a more serious note, one thing that I love about Harry is how the fandom and his live shows are such a safe place. I have never felt more like myself than I have at Harry shows. This environment is not only a testament to the fanbase but also to Harry himself. One of the most powerful displays of this support is when Harry helps fans come out at his shows.
(09) LA N2 Threewi
I’m sorry New York, but LA N2 walked so Long Island could run. On the last night of Harry Styles: Live on Tour, nobody wanted the night to end, including Harry, who graced the crowd with Kiwi, not once, not twice, but three times. As an original “threewi” survivor, I can confirm nothing will ever compare to the pure shock of hearing the song start for a third time.
(08) Banner at MSG
Notching countless awards and playing hundreds of shows, it’s easy for some of the achievements to muddle together. But this is one that can’t be forgotten. After completing a 15 night residency at Madison Square Garden and making history at the world’s most famous arena, the singer was presented with a banner to commemorate the moment that still hangs in the Garden to this day. He now has the same amount of banners in the arena as the New York Knicks.
(07) Long Hair Harry Haircut
If one thing is for sure, Harry’s hair has always been something connected to him. Perhaps one of his biggest moments broke the fandom with one Instagram post. Shoutout to Long Hair Harry, he will always be missed.
(06) His Vogue Cover
I would argue that all jokes aside, Harry's Vogue cover probably should go down in a top 10 list of his best career moments somewhere. Earning the spot as the first man to be alone on the cover of Vogue, Harry did so in a dress. Sparking controversy everywhere, the shoot certainly made a statement and cemented this achievement as one of his most powerful.
(05) His 2022 Grammy Performance
The leather vest, the green boa, his vocals. This performance was iconic and that’s all I really have to say about it.
(04) Sign of the Times in the rain at Wembley N1
You know how sometimes you can watch something happen and know that it’s a core memory for the people involved? This one I can guarantee is a core memory for Harry and fans alike. In his first sold out solo night at Wembley, rain started to pour during Sign of the Times creating a moment of magic and reflection for the star.
(03) Tattoo Roulette
A fan favorite moment, this one takes us back to 2015 in the thick of the Long Hair Harry era. In their last appearance on the Late Late Show, the One Direction boys were thrown into the debut of a new segment on the show, Tattoo Roulette. Spoiler Alert, Harry wound up the loser and became the proud owner of a new tattoo on live television.
(02) Shania Twain at Coachella Weekend 1
After Harry was announced as a headliner for Coachella 2022, fans everywhere were anxiously awaiting to see what he would pull out. Harrychella certainly did not disappoint. Weekend one saw an iconic guest in Shania Twain. I mean, I know I was floored by their duet of Man! I feel like a Woman.
(01) Ripping his pants at LA N13
It may have taken 13 years of touring in tight pants, but it finally happened: Harry ripped his pants on stage. But as resourceful as he is, he figured it out using his hands, a towel and a pride flag to cover the rip. Stellar problem solving skills there bud.