The Jack Schlossberg method

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I had a lovely week in Tbilisi, Georgia. Went to a sulfur bath, learned how dangerous Georgian chacha is, and ate A LOT of khachapuri. Want to thank the ZEG Storytelling festival for inviting me. It was a blast! I’m in the air today, making the long journey back to the States, but I’ve brought in Allegra Rosenberg to cover today’s issue. Back to our normal schedule Wednesday!

Before Allegra jumps in, first, a word from our sponsors…

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How Jack Schlossberg Mastered Being Online

—by Allegra Rosenberg

Jack Schlossberg, JFK’s only grandson, has become the darling of a particular set of extremely online twenty-somethings. Even those like me, who are not highly tuned in to the machinations of the Democratic party’s various failchildren, have become aware of Schlossberg’s sculpted bod and craggy face, his mischievous eyes and sultry voice… I digress. 

Since May, Schlossberg, whose previous social media content strategy had mainly consisted of surfing videos, has been publishing front-facing comedy videos of varying quality. 

As the videos began getting attention, they were covered by the New York Times, HuffPost, and other outlets who mainly (and understandably) focused on the videos’ political content, particularly Schlossberg’s array of anti-RFK Jr caricatures, done in different working-class accents, ostensibly in order to promote Biden’s campaign, an alignment he shares with his mother, Caroline Kennedy. 

But on TikTok his oeuvre is more diverse. He dances in grocery stores, strikes poses, sings Rihanna and Sinatra, and goes on various rants and rambles, to the delight of his growing fanbase. Of course, people knew who he was before — his Instagram has been active for many years — but this is the first time the general public has been given a taste of his vibe. 

As Ryan reported briefly last week, Town and Country Magazine published an interview with Schlossberg in which he explicitly described his social media strategy for the first time. The writer, William Cohan, a Wall Street expert who throughout the piece humblebrags about having gone to school with JFK Jr., Schlossberg’s uncle, shows off his other elite connections by contacting Schlossberg’s high-level family friends and making them explain how they don’t understand his deal either. “I just wish he’d kind of get it together,” said one source, who needs to lighten up. 

But Cohan is to be applauded for cornering the elusive scion and getting him to be honest about his approach. Schlossberg seems to really fundamentally get how Online works and how to go viral. “It’s a lot harder for a positive message to spread than it is for a takedown,” he said. “I think that if there was anything strategic about my videos, it was to try to combine those two things so that a strong opinion, which travels fast online, was combined with a serious set of facts. And I think that you need that combination in order to break through, and to make things exciting.” 

These things are true! Schlossberg seems to have a real head for social media marketing. Cohan then cajoles him into confessing that he has no immediate plans or desire to follow his family into politics, and casts this as a major disappointment to America. 

But it seems clear enough to me that Schlossberg’s comedy is not a way into politics. Instead the politics are merely a vessel for Schlossberg’s comedic aspirations. He has been auditioning for acting roles, according to his Town & Country interview. His accent and character work, including the posh economist Reginald Covington, is genuinely decent. His Twitter is, in my opinion, absolutely hilarious — observational comedy in the kind of over-earnest, sexual pseudo-Boomer tone of known posters like Dan Hentschel and Matthew Goldin. 

It’s not that he’s “jobless,” as some punters posit. The “prince of Camelot,” as The New York Times dubbed him, is an artist, dammit. Despite his Harvard Law bonafides he is clearly at heart a reincarnated Borscht Belt tummler, a man who is fighting with all the weapons he has at hand against the destiny of his dynasty. “Use your platform,” his family and advisors probably cajoled him — and a finger on the monkey’s paw curled. 

As writer Rachel Tashjian Wise pointed out on Twitter, there’s a strong distinction between his audience on Instagram and his audience on TikTok. The latter leans far younger and more in-on-the-joke, with none of the censorious “how dare you” of some Instagram normies. Jokes about “Little Edie” Bouvier of Grey Gardens fame, Schlossberg’s cousin via Jackie Kennedy, are in abundance, but these become grating and unoriginal in the face of the fact that Schlossberg’s comedy is a thing of its own. (Although if you dig it, you might also like comedians such as Zach Zucker and Michael Hirsch.) 

The esteemed commentators of /r/NYCInfluencerSnark report that while he’s allegedly very active on Raya, he isn’t crazy or putting on an act in his videos. He’s always been like this, apparently, “a little weird” but “sweet and respectful” — an overgrown theatre kid whose penchant for bits and goofs puts him at odds with the deeply serious political dynasty he was born into. 

Schlossberg’s excess of natural charisma carries his antics to a high echelon of enjoyability, with the potential — currently in action — to attract a large fanbase. “My type I fear,” viewers (female) say in unison. A video with his package on prominent display elicited a horny frenzy in the comments. “The people’s princess,” is the general consensus on a video of Schlossberg reciting Lord Byron’s “She Walks In Beauty” while wiggling on a Ripstik. 

Using the election as the occasion for a hard launch of his apparently long-practiced comedic skills, the “trust fund homeless” peripatetic is now the proud owner of a passionate, growing fanbase. Something that many a Democratic politician would kill for. Whether Schlossberg will jump headfirst into professional acting and comedy after the election, I have my doubts that he would enter into full-time serious political life after having a taste of what it feels like to be a star, with the more “unserious” aspects of his personality finally let out to play.

Alternatively, in a few decades we might see him riding all the way to the Presidency on the strength of his mincing acappella rendition of “Ticket To Ride”. Only time will tell.

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