Ivanka Trump And Jared Kushner Once Made A Bizarre Gossip Girl Appearance

As of 2021, there's a glossy new "Gossip Girl" on HBO — featuring a diverse cast, no less! — but millennials still remember the OG "Gossip Girl." The saga of "It" girl Serena van der Woodsen, her bestie Blair Waldorf, and their friends Chuck Bass, Nathaniel Archibald, and Dan Humphrey, was enough to launch the careers of Blake Lively and the gang. Viewers who tuned in to watch "the scandalous lives of Manhattan's elite" were treated to a host of guest stars, some of whom featured on the show before they became big names themselves.

Per Marie Claire, Hilary Duff, Lady Gaga, Liz Hurley, Michelle Trachtenberg, and Brittany Snow all made appearances on "Gossip Girl" throughout its six-season run. On Season 3, Duff starred as a super-famous celeb at NYU, who became romantically involved with Dan. In the same season, Gaga appeared as herself (of course), singing her bop, "Bad Romance." Snow featured in a flashback episode as young Lily Bass, while Trachtenberg made regular appearances as Serena's off-the-rails frenemy Georgina Sparks, who landed "S" in all kinds of trouble. As for Hurley, she was Nate's love interest in Season 5, as well as the editor-in-chief of the fictional New York Spectator newspaper.

That's not the comprehensive list of guest stars, though. Long before their days in the White House as part of the Trump administration, Ivanka Trump and Jared Kushner showed up at a party in "Gossip Girl" Season 4.

In the 2010 episode titled "Easy J," Ivanka Trump and Jared Kushner greet Lily van der Woodsen and Rufus Humphrey at a New York Observer party. The exchange is brief; Lily merely tells a glammed-up Trump that she "is a vision," while the "Women Who Work" author thanks the couple for coming. As Business Insider notes, Trump and Kushner's presence at the party made sense, given that Kushner owned the Observer at the time. Additionally, Trump regularly appeared on episodes of her father's show, "The Apprentice," so she was no stranger to the world of TV. Executive producer Joshua Safran told Vulture that the guest appearance was organic, explaining, "With Jared and Ivanka, it would've been, 'They're on a list and they're in town, reach out and see if they're available." Co-creator Josh Schwartz agreed, adding, "People wanted to be on the show, it was a crazy thing."

Though Trump and Kushner's cameo garnered backlash in the wake of Donald Trump's presidential run(s), Safran didn't look back in regret. "[Ivanka and Jared] are socialites in New York and they do fit the world of 'Gossip Girl.' I'm sure Lily van der Woodsen knows Trump and would have been on the board of charities with him or Melania. That's the world of 'Gossip Girl,' so to deny it would be wrong," he said. In all fairness, it makes sense — "Gossip Girl" tracks the who's-who of Manhattan society, and Trump and Kushner certainly fit the mold.

From Valentino to Marc Jacobs, "Gossip Girl" also heavily featured the high-fashion designers of the day. (Remember when Vera Wang was a guest star?) From Blair's headbands to Serena's sky-high stilettos, the characters' style influenced a generation of viewers. "New York style and being a [New] Yorker for 25 plus years definitely influenced how the cast dressed and the look of the girls," costume designer Eric Daman told Town & Country. "The essence of New York fashion DNA was essential in creating those characters." As a New Yorker herself, and with an eponymous line of clothing, shoes, and fine jewelry under her (designer) belt at the time of her cameo, Ivanka Trump was therefore naturally interested in the show. "I never miss an episode of 'Gossip Girl,'" she dished to InStyle (via Seventeen). "I think I'm a cross between Blair Waldorf and Lily van der Woodsen when it comes to [my personal] style. I like the uptown city style and a clean-cut, streamlined silhouette."

These days, it's hard to separate Trump from the political sphere, but Vanity Fair reports that she modeled long before she was a staple on her father's campaign trail. And Trump has always been interested in fashion. Even though her own brand shuttered, she has leveraged style as a tool to "shape her political identity," per Town & Country. Clearly, in her heyday, Trump was an "It" girl equal to the likes of Blair and Serena.