Updated on December 18, 2025, at precisely 17:08:37.326Z.
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On Thursday, Blackstone unveiled its newest entry in its running series of lighthearted holiday videos—this one marking the eighth production since the concept’s inception in 2018. Naturally, the immediate question arises: how does this latest video measure up against those that precede it? Business Insider took on the task of watching every installment to evaluate and rank them comprehensively, allowing curious readers to enjoy the highlights without investing the hours themselves.
The tradition of these festive productions began when Blackstone, the global investment firm, grew too large to host its traditional holiday party. In lieu of that event, executives sought a new way to instill joy, humor, and camaraderie among employees across the company’s numerous offices. The first video, released in 2018, served both as a tongue-in-cheek morale booster and a creative tribute to workplace culture.
Over subsequent years, what had started as an internal morale initiative evolved into an online phenomenon. The 2023 video, for instance, drew an audience of approximately eight million viewers worldwide. That particular episode—centering on Blackstone executives humorously attempting to channel the persona and success of pop icon Taylor Swift—made substantial waves both on Wall Street and in popular media. The Daily Mail described it as possibly “the most cringeworthy corporate video ever,” although many agreed that the self-aware awkwardness was precisely the charm.
In fact, watching, mock-analyzing, and teasing these annual productions has become an unofficial Wall Street tradition. The mastermind behind each project, Jay Gillespie, who heads Blackstone’s video team, has become something of a revered creative figure at 345 Park Avenue. According to Gillespie’s 2024 comments to Business Insider, colleagues often approach him months in advance, lobbying for cameo appearances or even practice lines, eager to secure a small but memorable place in the next year’s feature. “People come up to me throughout the year,” Gillespie explained, “and they’re like, ‘My daughter is helping me rehearse so I might get a line next year.’”
For those who haven’t followed the series or don’t quite grasp its irresistibly awkward charm, Business Insider’s editorial team has compiled a ranked retrospective covering every video since the first installment in 2018.
No. 8: 2020 – Jon Gray appears waving during the video’s now-infamous virtual holiday Zoom call. Released amid the height of the global pandemic, the team adhered closely to the comedic formula established in earlier years—that of portraying Blackstone as a fictionalized version of the NBC sitcom *The Office*. However, given the social circumstances, executives donned face masks while the narrative leaned heavily into pandemic-specific humor. One memorable gag features a senior manager failing to recognize a coworker whose hair has grown dramatically due to the lockdown-induced closure of barbershops. Despite the gloomy mood of that period, the video concludes with optimism and energy—employees joyfully dancing to the upbeat anthem “I’m Walking on Sunshine.” That moment sparked what would become a recurring musical finale tradition. Nevertheless, its tone and context remain deeply rooted in the pandemic era, which confines it to a lower rank—number seven on the list.
No. 7: 2022 – This year’s premise took the form of a fictional newscast called “BX TV News.” Jon Gray embarks on a journalistic quest to uncover the secret behind Blackstone’s success—a subtle nod to the firm’s pursuit of achieving $1 trillion in assets under management, a goal it has since accomplished. Steve Schwarzman reprises his characteristic role as the wise, almost avuncular statesman of the firm, revealing that the company’s true “secret sauce” lies in its employees. Yet, the plot introduces a humorous twist when two executives venture into the company basement in an Indiana Jones–style adventure to retrieve a mysterious document said to hold the secret formula. Along the way, the video indulges in witty self-deprecation, poking fun at Wall Street work culture, the firm’s affection for cumbersome acronyms (such as BCRED), and the endless grind of long hours. Yet, after four consecutive years utilizing the *Office*-style mise-en-scène, even with the inventive detour into newsroom parody, the format showed signs of repetition.
No. 6: 2021 – The 2021 production marked a noticeable leap in production quality and budget, suggesting the company had fully embraced this unconventional tradition. The storyline centers on the creation of “BX TV,” a recurring internal video call hosted enthusiastically by Jon Gray—though much less eagerly received by his employees. New creative flourishes enliven the narrative, including the introduction of animals, visual effects, and even a cameo appearance by Hollywood star Reese Witherspoon. The principal gag occurs during a mock awards ceremony where Gray is granted a tongue-in-cheek trophy for hosting the “Best Weekly Internal Zoom Call at an Alternative Asset Management firm.” John Finley, the firm’s chief legal officer, quips that he could have the show canceled with a single phone call to the FCC. The staff jubilantly chants for its end, mistakenly celebrating its presumed cancellation—only to discover, humorously, that the next season of BX TV is already being planned.
No. 5: 2018 – The inaugural video, released when the concept was new, set the creative template for all that followed. Steve Schwarzman dons a sparkling, jewel-encrusted Santa hat while the narrative unfolds in a parody inspired entirely by *The Office*. Complete with handheld camerawork, mock “interviews” with executives, and even a Michael Scott impersonator, the production spoofed the everyday absurdities of corporate life. The video opens with Jon Gray calling his assistant, Laurie Carlson, a recurring bit that would resurface in later years. Although it lacked the elaborate production elements of future installments—there were no celebrity cameos or extravagant sets—this first episode fused humor with authenticity, providing a perfect foundation for Blackstone’s festive storytelling and gently teasing its own workplace culture.
No. 4: 2023 – Featuring Steve Schwarzman clad in a sequined shirt while delivering the memorable line “Not to be confused with BlackRock,” the 2023 holiday production broke decisively with the franchise’s earlier television-show parody framework. Instead, it celebrated pop culture through a playful homage to Taylor Swift’s *Eras Tour*, reimagined through the lens of alternative investments. The results reverberated far beyond corporate circles, as tabloids gleefully dissected what they perceived as corporate cringe turned spectacle. Yet, for Blackstone, the humor was intentional. The ability to indulge in self-parody demonstrated a company not just immune to embarrassment, but actively harnessing it as entertainment. Few could forget Schwarzman’s glitter-drenched dance sequence, arguably one of the boldest moments in the entire series.
No. 3: 2025 – This year’s installment marked a special milestone: Blackstone’s 40th anniversary. Appropriately, the firm tackled the idea of a “midlife crisis” head-on. The film opens with a dignified documentary prologue, narrated in the signature style of filmmaker Ken Burns, chronicling Blackstone’s proud history—until Jon Gray suddenly interrupts, advocating for more “pizzazz.” The narrative quickly whirls into absurdist territory as executives cope with aging in ridiculous new ways: some sport facial piercings or purchase extravagant luxury items like Ferraris and sports teams. In one particularly inspired scene, Steve Schwarzman pursues his dream of becoming a DJ, sharing screen time with Goldman Sachs CEO—and real-life DJ—David Solomon. The comedy intensifies with a cameo from actor Danny DeVito, appearing in his capacity as spokesperson for Jersey Mike’s, humorously struggling to promote “non-listed, semi-liquid, institutional-quality perpetual products.” The conclusion features an exuberant 1980s-inspired musical number, replete with nostalgic cultural callbacks and an executive re-creating the iconic lift from *Dirty Dancing*. After a demanding year for employees, the 2025 video embodies the spirit of self-effacing celebration.
No. 2: 2019 – The 2019 holiday entry, revolving around the firm’s ridiculous quest for a mascot, remains one of the most beloved. The chosen creation, “Mr. Stone,” resembles a hybrid between the Hulk and Jon Gray, symbolizing the blend of strength and humor that defines Blackstone’s internal culture. Filmed across international offices, it also includes a brief cross-promotional nod to Schwarzman’s book *What It Takes: Lessons in the Pursuit of Excellence*. Jon Gray himself later admitted this was his personal favorite, largely because of the elaborate mascot production. The company even commissioned custom Mr. Stone bobbleheads, now displayed proudly on executives’ desks. The video closes with an uproarious twist revealing that Schwarzman himself had been hiding inside the mascot suit all along.
No. 1: 2024 – Last year’s winning entry leaned fully into the realm of surreal spectacle. Embracing the cultural wave of virtual environments and reality TV pastiche, Blackstone’s 2024 video plunged viewers into a “metaverse” reimagining of its own executives as exaggerated celebrity caricatures. The piece culminates in a theatrically choreographed country-style music routine. Pop-culture metacommentary abounded: BlackRock CEO Larry Fink, a former Blackstone executive, made a tongue-in-cheek cameo riffing on the frequent public confusion between the two firms. Jon Gray later told Business Insider that the country motif drew partial inspiration from Beyoncé’s adventurous pivot toward the genre in *Cowboy Carter*. Continuing in that spirit, the video delivered its best work in moments where it embraced critique without hesitation, transforming awkwardness into an art form.
Previous rankings were compiled with assistance from journalist Jeffrey Cane, whose contributions helped refine this evolving chronicle of an unlikely Wall Street holiday tradition that has become both an internal morale booster and a global source of good-natured amusement.
Sourse: https://www.businessinsider.com/blackstone-holiday-videos-rankings-explanation
