Harry Styles' Career Highlights (So Far), From Taylor Swift to 'SNL'

Harry Styles is getting ready to officially embark on his solo career, with his debut single on the way April 7. But even before Styles gets a chance to show the world what he's always wanted to do musically, he's managed to have some pretty monumental moments throughout his career as a singer -- aside from all his standout times in One Direction.

Ahead of the big release day, Billboard wanted to take a trip down Harry Styles memory lane and remind fans of all of the highlights he's already had. From Taylor Swift to his upcoming appearance on Saturday Night Live, below are 11 of Styles' biggest moments over the years.

Winning a Battle of the Bands competition with his first band White Eskimo (date unknown)

Before Styles was old enough to audition for singing competition shows, he prepped his vocal chops by acting as the frontman for a four-piece band of schoolboys called White Eskimo. He was obviously destined for stardom, as Styles helped White Eskimo claim a Battle of the Bands title when he was in Year 10 of school.

Earning a spot in One Direction through The X Factor U.K., July 2010

As a starry-eyed 16-year-old boy from a picturesque, yet "quite boring" town in England, Styles took the X Factor? stage for the audition that changed everything, crooning Stevie Wonder's "Isn't She Lovely" to Simon Cowell and Co. in April 2010. After being rejected as a solo artist, the judges thought he'd be great in a group alongside his fellow competitors Niall Horan, Liam Payne, Louis Tomlinson and Zayn Malik (brilliant intuition, we'd say). 

Dating Taylor Swift, November 2012-January 2013

Perhaps one of Taylor Swift's most famed -- and whirlwind -- romances, their fling was everything girls probably dream of: matching necklaces, hand-holding strolls through Central Park... the usual. Alas, they were not meant to be, officially calling it quits just a couple of months later in January 2013. Nevertheless, their short-lived romance did make for some pretty great song material for both of them down the line.

Sparking romance rumors (and vacationing) with Kendall Jenner, December 2015-March 2016

After things didn’t work out with one of music’s biggest names, Styles happened to strike a match with one of modeling’s biggest names. Although the two were never seen actually kissing, their trips to Anguilla and St. Barts (with her family, no less!) involved an awful lot of canoodling that certainly made it seem like they were more than friends -- yet, no official romance ever came of it.

?Blowing up the Twitterverse with a shout-out to his ex, February 2016

Styles and Swift’s breakup didn’t seem to involve many hard feelings, so when he turned 22 and decided to tell the world he was feeling his 2016 birthday -- in turn, quoting Ms. Swift’s famous song about the age -- fans went ballistic. In fact, the tweet had nearly 1 million likes and more than 700,000 retweets, making the Feb. 1 tweet the second most popular tweet of 2016. 

Landing his first movie role, March 2016

Although it was speculated that Styles would be the first to go solo of his band -- aside from the early-exiting Zayn Malik, of course -- Styles' first solo project actually proved to be acting. Renowned director Christopher Nolan apparently saw beyond the boy band, casting Styles in the war movie Dunkirk (due July 21).

Chopping his hair off, May 2016

From the beginning, Styles was always the 1D guy to be best known for his hairdo. The length was getting a bit out of control toward the end of One Direction’s run, and Styles decided that his group's hiatus was a perfect time to do something that makes Directioners lose their minds: Cutting it all off. Using an Instagram post of his hand holding the chopped ponytail, Styles revealed that he did it for charity (The Little Princess Trust). With no reveal as to how the fresh haircut looked, it wasn’t until he posed for a picture with a fan that his new look was unveiled.


Whoops. #Littleprincesstrust

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Signing a solo deal, June 2016

As excited as fans were about getting to see Styles in a film role, what they were most eager to know was when he'd be releasing his own music. They got one step closer to the answer to that over the summer, when Billboard was told that Styles had signed a deal with Columbia Records -- the same label behind One Direction.

Becoming a magazine cover star, September 2016

Although Styles' record deal didn't involve any new music right away, his solo ventures landed him his first cover spot. He posed for some rather off-the-wall shots for fashion publication Another Man. Ironically, the issue became available on the same day that 1D bandmate Niall Horan dropped his first solo single, "This Town," and announced his own record deal (Sept. 29).


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Dropping his first solo single, April 2017

Letting months pass with no hints or indication that his first sign of solo music was on the way, Styles used a sneaky commercial spot in the U.K. on March 25 to reveal that something was coming April 7 -- which Billboard was told is his first solo single. While there was no indication of what exactly his solo material would sound like, the timing of his announcement only left two weeks for fans to wonder. 

Appearing on Saturday Night Live, April 2017

No, this hasn't happened yet, and we haven't even heard what kind of music Styles has whipped up. But before the world even gets to hear what Styles has in store, he got an invite to have him perform on one of the most acclaimed stages on television. If that isn't an indication of the kind of success he's about to have from here on out, we're not sure what is.