Leaving a beloved group to fly solo can be risky, especially when the artist is trying to establish himself as an adult who has moved beyond his teen-pop past. It’s a delicate balance: You want to assert your maturity without alienating your core audience or resorting to inauthentic shock. But Styles has handled the transition well, and this playlist puts him in a lineage of others who have done something similar in the past, whether that’s Michael Jackson, Justin Timberlake or a slightly edgier English pop rogue, Robbie Williams. It also contains a solo hit from another member of One Direction, but you’ll have to listen to find out which one.