Annie Leibovitz has spent decades creating some of the most recognizable celebrity photographs in modern pop culture. Her portraits have appeared on the covers of major magazines, documented musicians at defining moments, and challenged conventional ideas about celebrity, beauty, identity and fame.
From intimate celebrity portraits to images that became cultural landmarks, Leibovitz has never been afraid to approach her subjects from an unexpected angle. Her photographs often capture more than a famous face—they tell a story about the person, the era and the culture surrounding them.
Her work on the 2016 Pirelli calendar was another example of that approach. Instead of focusing primarily on traditional glamour and supermodels, the project highlighted accomplished women from different fields, including entertainment, art, sports and business.
Leibovitz's career has included remarkable assignments for Rolling Stone and Vanity Fair, as well as work with some of the world's biggest musicians, actors and cultural figures. Here are ten of her most memorable photographs that helped push celebrity photography in a new direction.
10. Caitlyn Jenner on the Cover of Vanity Fair
The portrait marked a highly publicized moment in Jenner's transition and quickly became one of the most discussed magazine covers of the year. Leibovitz's photography presented Jenner in a polished yet personal setting, helping create an image that became closely associated with an important moment in popular culture.
9. Mick Jagger
Leibovitz's relationship with musicians became one of the defining parts of her early career. Her work with the Rolling Stones gave her the opportunity to photograph Mick Jagger both onstage and behind the scenes.
This memorable 1975 portrait shows Jagger in a robe with a towel wrapped around his head after a performance in New York. It offers a very different view of the legendary frontman, capturing a relaxed moment away from the intensity of the stage.
The photograph also reflects Leibovitz's ability to make extraordinary celebrities appear surprisingly human and approachable.
8. Leonardo DiCaprio
Before Titanic transformed Leonardo DiCaprio into one of Hollywood's biggest stars, Annie Leibovitz photographed the young actor during the early stages of his rise to fame.
The imaginative portrait captures DiCaprio with a swan wrapped around his neck, creating an unusual visual that is far removed from the conventional celebrity studio portrait.
At the time, DiCaprio was already attracting enormous attention after roles including Romeo in Baz Luhrmann's Romeo + Juliet. His career was about to reach another level, making this photograph an interesting snapshot of the actor before worldwide superstardom.
7. Keith Haring
Keith Haring was known for his instantly recognizable artwork, energetic lines and bold imagery. Leibovitz photographed the celebrated artist only months before his death in 1990, creating an image that reflected his distinctive artistic personality.
Haring believed art should be accessible to everyone. His work appeared in public spaces throughout New York, and he frequently used his art to communicate ideas about society and popular culture.
Leibovitz's portrait captures that creative spirit by placing Haring himself within a visual environment reminiscent of his own artwork.
6. Demi Moore
Demi Moore appeared in another striking Leibovitz photograph for Vanity Fair in 1992. The actress was photographed with a suit painted directly onto her body, creating an image that deliberately blurred the boundaries between fashion, photography and art.
The unusual concept immediately attracted attention and became one of the magazine's most memorable covers. Rather than relying on a conventional fashion portrait, Leibovitz transformed Moore into part of the artwork itself.
It was another example of the photographer's willingness to challenge expectations surrounding celebrity imagery.
5. Angelina Jolie
In 2005, Annie Leibovitz photographed Angelina Jolie for a striking portrait that showed the actress in a bathtub. The minimalist setting placed the focus on Jolie's tattoos, expression and distinctive screen presence.
At the time, Jolie was promoting Mr. & Mrs. Smith, the film that would become an important chapter in her career. The photograph appeared during a period when public interest in the actress was already extremely high.
As with many Leibovitz portraits, the image combined celebrity glamour with an unconventional setting, making it instantly recognizable.
4. Whoopi Goldberg
One of Annie Leibovitz's most memorable celebrity portraits features Whoopi Goldberg surrounded by milk in a bathtub. The playful image was inspired by a routine from Goldberg's stand-up comedy.
The concept transformed a humorous story into an unforgettable visual. Goldberg's expression and playful pose gave the photograph an almost surreal quality while also making a statement about identity and beauty.
The result became one of the most recognizable photographs from Leibovitz's early career and remains a powerful example of how humor can be turned into striking editorial photography.
3. Tom Ford's Hollywood Portrait
The annual Vanity Fair Hollywood issue has become famous for bringing together major actors and filmmakers in elaborate group portraits. One particularly provocative edition featured designer Tom Ford alongside actresses Keira Knightley and Scarlett Johansson.
The image created plenty of discussion because of its contrast between the unclothed actresses and the fully dressed Ford. The photograph demonstrated Leibovitz's ability to create an image that was both glamorous and deliberately provocative.
It also became part of the larger tradition of memorable Hollywood magazine covers designed to capture the personalities expected to dominate the awards season.
2. Pregnant Demi Moore
Few magazine covers have had the cultural impact of Annie Leibovitz's 1991 portrait of a pregnant Demi Moore. The actress appeared on the cover of Vanity Fair while seven months pregnant, proudly displaying her baby bump.
At the time, the decision to publish such an intimate maternity portrait was considered groundbreaking. Celebrity pregnancy was rarely presented so openly in mainstream magazines, particularly on the cover of a major publication.
The photograph helped change the way pregnancy and celebrity were represented in popular media. It became an enduring example of how a single photograph can challenge established ideas about beauty, femininity and public image.
1. John Lennon and Yoko Ono
At the top of the list is perhaps Annie Leibovitz's most famous and emotionally powerful portrait: John Lennon embracing Yoko Ono.
The photograph was taken on December 8, 1980, just hours before Lennon was killed outside his New York City home. The assignment had originally been focused on Lennon, but he wanted Ono included in the portrait.
Leibovitz created a striking composition in which Lennon, unclothed, curls around a fully dressed Ono. The contrast between the two figures creates an image that feels intimate, vulnerable and deeply emotional.
The photograph became even more significant because of what happened later that day. Published after Lennon's death, it transformed from a celebrity portrait into an enduring cultural image associated with love, loss and one of music history's most tragic moments.
The Lasting Influence of Annie Leibovitz
Annie Leibovitz's photography stands out because she rarely treats celebrity portraits as simple photographs of famous people. Instead, she builds visual stories around her subjects, often using unusual settings, symbolism, humor or unexpected contrasts.
Her work with musicians, actors, artists and cultural figures has helped define the visual language of modern celebrity photography. From the intimate portrait of John Lennon and Yoko Ono to the groundbreaking image of pregnant Demi Moore, her photographs have repeatedly challenged expectations.
That ability to turn a single photograph into a cultural conversation is what makes Leibovitz's work so enduring. Decades after many of these images were created, they remain instantly recognizable and continue to influence how celebrities are photographed and presented to the public.