Unforgettable Glamour: Inside Vanity Fair’s Iconic Hollywood Issue Featuring Zendaya, Oprah, and A-List Stars

The annual Hollywood Issue of Vanity Fair consistently captures the essence of contemporary cinema, blending legendary figures with rising stars to create a timeless portrait of the industry. The 24th annual edition was no exception, delivering a cover that resonated deeply within popular culture and showcased an extraordinary constellation of talent. This particular issue, released at a significant juncture for Hollywood, brought together twelve of the most influential and celebrated actors, creating a visual narrative that was both powerful and inspiring. From multi-generational icons to the fresh faces shaping the future, the cover was a testament to the diverse landscape of Tinseltown.

Anchoring this remarkable ensemble were industry heavyweights whose careers have left an indelible mark: the incomparable Robert De Niro, the universally beloved Tom Hanks, and the unparalleled media mogul Oprah Winfrey. Their presence alone signaled the profound gravitas of the issue, representing decades of cinematic excellence and cultural impact. Standing alongside these titans were stars who had recently commanded significant attention, including Big Little Lies actresses Nicole Kidman, then 50, and Reese Witherspoon, then 41. Both Kidman and Witherspoon exuded an aura of refined power and elegance, embodying the success of their critically acclaimed series and their ongoing influence as producers and performers. Their inclusion highlighted a period where women were increasingly taking control of their narratives in Hollywood, both on and off screen.

Adding a vibrant, youthful energy to the cover was the rising sensation Zendaya, then just 21 years old. Her striking appearance, characterized by very minimal makeup, starkly contrasted with her dazzling, low-cut sequin gown. This choice emphasized her natural beauty and inherent confidence, making a strong statement about authenticity in an industry often associated with elaborate artifice. Zendaya’s ability to command attention with such a bare face, juxtaposed with high-fashion glamour, cemented her status as a genuine style icon and a powerful voice for her generation. The cover also held historical significance as it marked the final issue overseen by longtime Editor-in-chief Graydon Carter, who had helmed Vanity Fair for an impressive 25 years, leaving an enduring legacy on the publication.

The visual masterpiece adorning the cover was brought to life through the lens of the legendary photographer Annie Leibovitz. Known for her iconic and intimate celebrity portraits, Leibovitz meticulously captured the essence of each star in settings spanning both Los Angeles and New York. Her unique ability to draw out the genuine character of her subjects is precisely what makes her work so compelling. Oprah Winfrey herself eloquently articulated the experience of working with Leibovitz, stating, “The thing about working with Annie Leibovitz is allowing yourself to lean into the power and grace of her. She’s a force; she knows what she wants. She sees things that you can’t see.” This insight underscores Leibovitz’s unparalleled artistic vision and her capacity to transform a group of individuals into a cohesive and captivating narrative, solidifying her status as one of the most influential photographers of our time.

Beyond the core ensemble, the issue further celebrated a diverse array of talent, featuring stars who had recently captivated audiences with their groundbreaking roles. Among them was Gal Gadot, the embodiment of a modern superhero as Wonder Woman, whose powerful portrayal redefined the character for a new generation. Her inclusion on the cover underscored the growing demand for strong female leads in blockbuster cinema. Also gracing the pages was Claire Foy, who garnered widespread acclaim for her regal and nuanced performance as Queen Elizabeth II in Netflix’s prestigious series, The Crown. Foy’s elegant presence represented the sophisticated storytelling finding a global platform through streaming services, elevating the craft of acting to new heights. Each star was meticulously chosen not just for their fame, but for their significant contributions to the evolving landscape of entertainment.

Further adding to the visual splendor was the captivating presence of Jessica Chastain, who commanded a prominent position front and center on the cover. Dressed in a bold, striking red ball gown, Chastain’s image exuded confidence, sophistication, and a touch of dramatic flair. Her powerful pose and vibrant attire made her an undeniable focal point, symbolizing the strength and resilience of women in Hollywood. The careful selection of attire for each star contributed significantly to the overall aesthetic and message of the cover. This thoughtful curation extended to the beauty choices as well, highlighting individual styles while maintaining a cohesive sense of glamour and sophistication throughout the entire spread, ensuring every detail contributed to the issue’s iconic status.

The meticulous attention to detail extended to the styling of each woman, creating a symphony of personalized glamour. Reese Witherspoon’s hair was styled in soft, cascading waves, parted in the center, which perfectly framed her face and added to her approachable yet sophisticated look. Both Jessica Chastain and Claire Foy sported gorgeous, striking red lips, a classic choice that conveyed confidence and timeless elegance, complementing their powerful on-screen personas. In contrast, Nicole Kidman opted for a softer, delicate pink lip, which beautifully accentuated her porcelain complexion and added a touch of subtle grace. Gal Gadot’s stunning hair was artfully styled in undone waves by the renowned stylist Mark Townsend, lending her an effortlessly chic appearance. Furthermore, her makeup was flawlessly executed using Revlon products, a fitting detail given her recent appointment as the new face of the iconic beauty brand. This strategic collaboration not only highlighted Gal’s beauty but also brought a contemporary commercial edge to the high-fashion editorial. The entire presentation was an inspiring and powerful image, celebrating diverse forms of beauty and strength.

This particular Vanity Fair Hollywood Issue was more than just a collection of famous faces; it was a cultural artifact, capturing a pivotal moment in Hollywood’s history. It represented a confluence of eras—the enduring legacy of veteran actors, the established power of current leading ladies, and the ascendant influence of a new generation. The cover and its accompanying portfolio told a story of evolution, diversity, and the unwavering appeal of cinematic storytelling. It underscored the magazine’s role as a chronicler of fame and fortune, artistry and ambition. The meticulous planning, the legendary photographer, and the curated selection of stars all contributed to an issue that continues to be referenced as a benchmark for celebrity portraiture and editorial excellence, solidifying its place in the annals of pop culture history.

What were your favorite moments or stars from this iconic Vanity Fair Hollywood Issue? Share your thoughts on this legendary celebration of cinematic talent and style!