What the Hell Is Jack Schlossberg Doing?

Being a “media personality” seems like an amorphous and kind of maddening experience. How do you define a moving target like “success” when it depends on things forever in flux like the state of media and audience reaction? The position seems bound to produce miscalculations and mistakes as often as it produces something that works. This is about how much I’m willing to be sympathetic to someone like Jack Schlossberg, a Kennedy scion, TikTok personality, and Vogue’s political correspondent who seems determined to flame out by making the most chaotic, yet lame choices he can.

When Vogue brought him aboard, the self-described “silly goose” seemed determined to bring levity to his political coverage. He seemed like a good person to do it and chose his targets well, like when he mocked RFK Jr. But now? Well, now he’s pulling weird, tone-deaf, and unfunny “jokes” that feel way more obnoxious than silly. How else am I supposed to describe how he pretended to be Baldoni’s beleaguered lawyer in the middle of the Blake Lively/Justin Baldoni feud/scandal?

Commenting on a hot topic to stay relevant is one thing, but what is this? Assuming it’s meant to be a joke, what is the joke? What’s the angle? This reads like someone grasping for something, but I couldn’t possibly tell you what. And then there was just yesterday when Schlossberg took to X to post this deeply dumb query:

It’s a very stupid, shallow, and ridiculous question, but I’m frankly too busy rolling my eyes to be offended. Taking out of the equation how weird and unseemly it is to discuss how “hot” your maternal grandmother is, what the hell is Schlossberg doing here? As before, what is the joke? This feels so lazy and bizarre that it doesn’t read as comedy or provocation; just words thrown together like salad. If he’s meant to be a political correspondent, then what is his angle?

Maybe it’s not that complicated. Maybe he’s caught on his back foot and is scrambling hard to find any lightheartedness in our pretty dire political situation. Maybe he’s bored or too online or over-validated or all of the above, but whatever’s going on, this nonsense just isn’t it. It’s uninteresting chaos, it’s unfunny jokes, and it’s quite annoying. Whatever Schlossberg is doing, let’s hope he cuts it out soon or else he may flame out just as he was reaching a new height.