Top 20 Times Harry Styles Was Awesome

Harry’s hair has always been an essential part of his image. In fact, it’s even in his name! Over the years, fans have enjoyed seeing how his hairstyle transforms and have even designated certain looks as “eras”. A particular fan favorite was the long hair he sported in the later years of One Direction. In 2016, Harry shocked fans when he chopped off his long tresses for his role in the film “Dunkirk.” The transformation was documented in the behind-the-scenes film that accompanied his debut solo album. While we hated to see the long hair go, we were appeased when we heard that Harry donated the hair to The Little Princess Trust, a charity that creates real hair wigs for children.

Has there ever been a celeb duo as iconic as Harry and Lizzo? Their friendship started back in December 2019, when Harry covered Lizzo’s song “Juice” at the BBC Radio 1 Live Lounge and sang her praises in the accompanying interview. While fans loved seeing Lizzo acknowledge Harry’s cover on Twitter, that was nothing compared to what came a month later. At the SiriusXM & Pandora Opening Drive Super Concert Series, Lizzo ended her set by bringing out the singer-songwriter to sing “Juice.” Their platonic chemistry, both onstage and off, is incredible, and we’d be lying if we said we weren’t secretly hoping that the two would release a studio version of the duet.

Most of us have dreamed about running into our celebrity crush in real life. But for this fan, her dream came true… almost. Like a scene out of a movie, a fan named Theadora came home one day to find a once in a lifetime note waiting for her. Though she narrowly missed meeting Styles, she still got an experience most fans would kill for. In addition to the note, personally invited her to attend a concert, and signed her copy of his album, “Fine Line.” Oh, and he posed for a photo while he fed her fish. While the signed merch would be nice, the story of Harry feeding our fish would be invaluable.

Winning a prestigious award is a huge accomplishment in any artist’s career. It’s an opportunity that most people dream about. No one wants to miss the chance to accept their award in person—and certainly not for the reason Harry nearly missed accepting this one! At the 2014 BRIT Awards, One Direction was honored with the Global Success Award to celebrate their achievements as a band. However, when they were called onstage to accept their award, they were missing a certain bandmate. About halfway through their speech, Harry came running through the audience to the stage and his reason for being late was pretty hilarious. It goes to show that celebrities really are just like us. Even they can have an embarrassing moment now and then.

Harry has always been a big part of the LGBTQ+ community and his concerts are no exception. He goes out of his way to ensure that they are safe, welcoming places for everyone in attendance. At the start of each show, he encourages everyone to be their most authentic selves. Not only has this created a fun atmosphere for concert-goers, but it has prompted many fans to even come out through Harry. One fan even came out to her mom who was seated in a different section at a Milwaukee stop on the 2021 Love On Tour. Whenever we see Harry help a fan come out, it makes us wish we were there in the audience, cheering them on.

When it comes to fashion, Harry has established himself as someone to watch in recent years. So it wasn’t a surprise when it was announced that he would be co-hosting the 2019 Met Gala alongside Lady Gaga, Serena Williams, Anna Wintour, and his frequent collaborator, Gucci’s Alessandro Michele. The theme of the gala was “camp,” and while we had no doubts, Harry definitely pulled through. He worked with Alessandro Michele and stylist Harry Lambert to create a show-stopping look for the event. In a sheer top and black extra high-waisted trousers with a pearl drop earring, Harry proved that he earned his place on the pink carpet.

It’s no secret that Harry Styles and James Corden are long-time friends. The pair have worked together in various capacities, including appearing in a Gucci ad and even sharing a kiss on a British game show. But one truly iconic moment took place on “The Late Late Show.” The popular “Crosswalk the Musical” segment was reimagined as a concert for Harry to promote his sophomore album, “Fine Line.” From handing out flyers to performing hit singles “Kiwi,” “Lights Up,” “Watermelon Sugar,” and “Sign of the Times,” Harry brought his A-game. We definitely wouldn’t mind getting stuck in traffic if it meant having this view.

Harry Styles is the whole package. He’s talented, handsome, and stylish. But his personality is really the cherry on top. His onstage presence proves he’s a natural-born performer and he always knows exactly how to excite a crowd. One way that he does this is through a callback to his One Direction days. Back in 2015, during an interaction with the crowd at a concert, Harry made a cheeky joke about their show being family-friendly. From there, the quip turned into an inside joke with the fans that he’s carried onto his own shows today. Every time Harry pulls this old gem out at his concerts, the fans go crazy, and honestly, we don’t blame them.

It’s no secret that Harry Styles likes getting tattoos… In fact, he likes them so much that he doesn’t mind doing it on live television – which he proved by getting yet another tattoo on “The Late Late Show with James Corden.” On that particular evening in 2015, the British show host invited the members of One Direction to a friendly game of tattoo roulette. Everyone was understandably nervous… especially Niall and James, as the only tattoo virgins present. Fortunately for them, the unlucky victim turned out to be Harry. The young singer was forced to get a “Late Late Show” tattoo on his arm; but true to himself, he took it like a good sport.

If there was a Harry moment to remember in 2020, it was his American Vogue cover. In the nearly 130 years of its distribution, Harry’s appearance marked the first time that a male appeared on the cover alone. Dressed by Gucci’s Alessandro Michele, Harry donned a frilly blue dress that sparked a wider debate about gender expression through fashion. While many commended Harry’s look, others weren’t as supportive. Political commentator Candace Owens famously denounced Harry’s choice to wear a dress, calling for a return of “manly men” on Twitter. And Harry clapped back in the best way possible by posting a shot of him in a lace-trimmed blue suit with a banana and a caption that simply read: “Bring back manly men.”

Harry Styles has never been shy about his support for the LGBTQ+ community. Over the years, he’s become an inspiration to many of his young queer fans. During a concert, the pop star spotted a young girl holding up a sign that said she was going to come out to her mom, thanks to him. Upon hearing that her mom’s name was Tina, Styles shushed the whole stadium… only to record himself yelling into the microphone, “Tina… she’s gay!” Unsurprisingly, videos of the sweet scene went viral immediately. Best part of it all? The fan later shared her mom’s reaction on Twitter: Tina was reportedly “overjoyed” and thanked Harry for supporting her daughter.

2017 was a busy year for Harry Styles, what with his worldwide tour and the launch of his first solo album. But his music career wasn’t the only thing that was taking off: in July, Harry starred in Christopher Nolan’s blockbuster, “Dunkirk.” Alongside actors like Cillian Murphy and Fionn Whitehead, the pop star played a young soldier named Alex. While this was uncharted territory for him, Styles’ performance was praised by critics and audiences alike for its poignancy. It just goes to show that Harry is far more than a pretty face with a golden voice; and though we can’t wait to hear more of his songs, this promising big screen debut assures us that he also has a bright acting career ahead of him.

We know we said no music videos, but what we meant was no musical performances from them. And fortunately, “Dunkirk” wasn’t the only time we got to see Harry show off his acting chops. Years earlier, we saw him play a more light-hearted character in the video for One Direction’s hit single, “Best Song Ever.” While each of the boys had a specific bit, Harry Styles stood out as the band’s dorky marketing manager, Marcel. The character’s adorable clumsiness and over-the-top enthusiasm were a stark departure from Styles’ usual charming self; not to mention, it was hilarious to see Marcel’s ideas get shot down by the “real” Harry. While we look forward to seeing more of his acting, we think it’s safe to say that Marcel the marketing guy remains one of his most memorable performances.

A standout segment of Harry’s concerts has always been his fan interactions. Regardless of the show, he always makes sure to take time to interact with the crowd, respond to their signs, and even have quick conversations. At a 2018 concert in Florida, Harry had a moment with a couple of fans in the crowd that went down in history. After noticing they were holding cups, Harry asked them what they were drinking. When they replied “vodka”, he tried to confirm that they were drinking vodka straight, but the words got a bit misinterpreted, leading to this hilarious reaction. Since then, the moment has become a staple within the fandom, even being used in fan-made merchandise.

It’s a known fact that Harry Styles has iconic tastes in both music and fashion; so, in retrospect, we shouldn’t have been surprised to see him pay homage to a fellow icon on Halloween. Still, the entire Internet was floored when Harry showed up to the annual Casamigos Halloween party dressed as pop music legend Elton John in 2018. The look included a sparkly L.A. Dodgers top, a matching baseball cap, and rhinestone-studded pink sunglasses. The outfit was reminiscent of a 1970s-era Elton John, and like much of Harry’s wardrobe, was designed by Gucci. Not only did Styles win costume of the year, he also got the seal of approval from Elton John himself, who shared pictures of the outfit on his Instagram.

We always knew that Harry Styles had a mischievous side; just look at that cheeky grin of his. So what do you get when you put him on the same set as comedy legend Ellen DeGeneres? Apparently, one hilariously awkward pizza delivery. In this hidden camera prank, Harry chatted with a pizza delivery guy while Ellen told him what to say through an earpiece. As you’d expect, she was merciless. But we suspect that Harry enjoyed it just as much – if not more. Not only was the segment hysterical, it was also yet another chance for us to see his amazing acting and improv skills. Also, we give props to the pizza delivery guy (or should we say, “broooo”) for being so chill.

While we can’t agree on everything, it seems that everyone loves Shania Twain. Even Harry Styles isn’t immune. Over the years, Harry has made several callouts to the country-pop star. So there was no better guest to take the stage with him as he headlined the first night of the 2022 Coachella Valley Music and Arts Festival than Shania herself. The pair dazzled in matching rainbow-sequined outfits as they performed two of her biggest hits, “Man! I Feel Like A Woman!” and “You’re Still the One.” Their voices and onstage personalities worked together in perfect harmony and we’d love to see the two pair up again in the future.

It’s rarely easy to stay friends with an ex, but Styles makes it look like a piece of cake. When the young rockstar guest hosted “The Late Late Show”, he reconnected with his old flame, Kendall Jenner. The two engaged in a high-stakes game of Spill Your Guts or Fill Your Guts, in which they had to choose between answering an embarrassing question or eating something gross. While the producers had come up with some seriously loaded questions, Jenner and Styles managed to skirt around the awkwardness and had a great time in the process. Their romance might have ended a long time ago, but it was heartwarming to see Harry maintain such a playful, easy rapport with his ex-girlfriend.

Harry Styles has had plenty of iconic moments as a guest on “Saturday Night Live.” Who could forget his spot-on imitation of Mick Jagger’s swagger back in 2017? However, he’s also one of the lucky stars to have had the honour of pulling double duty on SNL, appearing as both host and musical guest. Styles kicked off the evening with a monologue in which he fondly mentioned his One Direction comrades… and not-so-subtly roasted Zayn Malik. His sketches included a parody of Jordan Peele’s “Get Out,” and a hilarious bit in which he played a social media manager who just couldn’t hide his thirst for Nick Jonas. Needless to say, Harry’s charisma and acting skills definitely gave us one Saturday night to remember.

Before we unveil our top pick, here are a few honorable mentions.

His “As It Was” Look
That Red Sequined “As It Was” Outfit

Telling a Fan to Go to Therapy
(In a Supportive Way)

Inducting Stevie Nicks Into the Hall of Fame
“34th Annual Rock and Roll Hall of Fame Induction Ceremony” (2019)

Harry Styles and James Corden share one of the best celebrity friendships out there. After all, only a true friend guest-hosts your show when you have to go to the hospital for the birth of your daughter, right? If we had to pick just one, we’d say their most iconic moment came in 2017, when Harry first appeared as a solo artist on James’ Carpool Karaoke segment. The episode had it all: great music, bold fashion experiments, and of course, rom-com reenactments. Who knew Harry made such a good Julia Roberts? There might just be something magical about putting these two in a car together: when the carpooling buddies in 2019 with James in the passenger seat, they still had the same off-the-charts chemistry.