Justin Timberlake’s Air of Desperation

Once upon a time, having Justin Timberlake on Saturday Night Live would have been a thrilling thing. In the mid-2000s, the pop star emerged as one of the show’s favorite recurring hosts, the kind of mega-famous celeb who seemed like he would be down for anything, such as dressing up in a giant mascot costume or putting his, ahem, dick in a box.

But the tide has turned on Timberlake. He arrived on this weekend as a musical guest with album , his persona has also undergone a cultural reckoning, especially in light of the revelations about him found in his , among them that she because he “wasn’t happy about the pregnancy.” She wrote that Timberlake tried to serenade her with his guitar while she was in pain, and then went on to as “a harlot who’d broken the heart of America’s golden boy” after they broke up. Between that and a reevaluation of his role in the Janet Jackson Super Bowl scandal of 2004, in which he got off relatively scot-free while Jackson was pilloried, Timberlake has become emblematic of a casual mid-2000s white-male cockiness that doesn’t play as well in 2024.