Jon Hamm Marries Anna Osceola in Enchanting Big Sur Wedding: A Star-Studded Celebration and Love Story Fulfilled
Hollywood heartthrob and Emmy Award-winning actor Jon Hamm, 52, has officially tied the knot with his long-time girlfriend and former Mad Men costar, Anna Osceola. The couple exchanged heartfelt vows in a breathtaking seaside ceremony held at the picturesque Anderson Canyon in Big Sur, California, on Saturday, one year after their engagement. The highly anticipated nuptials brought together a glittering array of celebrities and served as a delightful reunion for cast members of the iconic series that first brought the pair together.
The stunning outdoor event was captured in photographs, which quickly circulated online, showcasing the radiant bride and dapper groom. The natural beauty of the Big Sur coastline provided a spectacular backdrop, enhancing the romantic and intimate atmosphere of their special day. Guests were treated to an unforgettable experience, celebrating the union of one of Hollywood’s most beloved and private couples.
A Vision of Elegance: Wedding Attire and Coastal Setting
The ceremony at Anderson Canyon was nothing short of a fairy tale. Jon Hamm, known for his impeccable style, looked effortlessly classic in a perfectly tailored black tuxedo, exuding sophistication and charm. His bride, Anna Osceola, stole the show in an eye-catching, strapless white gown that perfectly complemented her figure and the elegant coastal setting. Her choice of attire was both timeless and modern, embodying the essence of bridal grace.
Anna’s long hair was styled down, parted in the middle, allowing its natural beauty to frame her face. She opted for modest, delicate jewelry and understated makeup, ensuring her natural radiance shone through. The couple was photographed walking arm-in-arm, a picture of pure bliss, as they made their way through the cheering crowd of supportive guests. A particularly poignant moment captured was the newly married couple sharing a tender kiss at their outdoor altar, symbolizing the beginning of their beautiful journey together as husband and wife.

Mad Men Reunion and A-List Revelry: The Reception Details
The celebration continued with a reception reportedly brimming with delightful details and a vibrant atmosphere. Adding a unique and nostalgic touch, guests were treated to Mad Men-themed cocktails, a playful nod to the iconic show where Jon and Anna’s paths first crossed. This thoughtful detail not only entertained guests but also paid homage to a significant chapter in the couple’s lives and careers.
The guest list was as star-studded as one would expect for a celebrity wedding of this caliber, featuring a dazzling roster of A-list personalities. Among those spotted celebrating with the happy couple were actors Billy Crudup, the ever-charming Paul Rudd, and the comedic genius Tina Fey. Perhaps the most anticipated attendee for fans of the show was Mad Men‘s own John Slattery, whose presence transformed the wedding into an epic, albeit intimate, Mad Men reunion. The camaraderie and joy shared amongst the cast members underscored the deep bonds formed during their time on the critically acclaimed series.
The musical choices for the evening were equally memorable. The walk-up song for the ceremony was reportedly the iconic theme from the 1967 James Bond film, You Only Live Twice. This classic, sophisticated choice perfectly set the tone for a romantic and elegant affair, reflecting the couple’s discerning taste and adding a touch of cinematic grandeur to their special moment. The entire event was meticulously planned to ensure every detail contributed to a truly unforgettable experience for both the newlyweds and their cherished guests.
From Sterling Cooper to Soulmates: Jon and Anna’s Love Story
Jon Hamm and Anna Osceola’s wedding culminates a beautiful love story that began years ago. Their journey to the altar commenced over a year after they got engaged, marking a significant milestone in their relationship. The lovebirds first crossed paths in 2015 on the set of the Emmy-winning series Mad Men. Anna made a memorable appearance in the show’s grand finale, playing Clementine, a receptionist at a retreat, and it was clear that she made a lasting impression on Hamm, both on and off-screen.
Their relationship blossomed quietly over the years, away from the intense scrutiny of the public eye. The first instances of them being seen together casually emerged in 2017, sparking initial rumors of a burgeoning romance. Despite their celebrity status, they largely maintained a private life, choosing to let their relationship develop organically and away from the tabloids. However, as their bond deepened, they became more comfortable with public sightings. By early 2020, they were spotted engaging in everyday activities, such as picking up groceries together, signaling a clear progression in their romance. Their first official public appearance as a couple, making their red carpet debut, came in 2022, a prelude to their engagement and subsequent marriage.
Their gradual journey from on-screen colleagues to real-life partners underscores a genuine connection built on shared experiences and mutual affection. Fans have long admired their discreet approach to their relationship, celebrating their happiness as they’ve slowly opened up about their bond. The wedding in Big Sur is not just a celebration of their love, but a testament to a relationship that has grown beautifully and authentically over time.

Anna Osceola: An Emerging Talent
While often recognized for her role in Mad Men and now as Jon Hamm’s wife, Anna Osceola is an accomplished actress in her own right. Beyond her brief but impactful appearance in the series finale of Mad Men, she has built a solid career with appearances in numerous television series and films. Her credits include roles in popular shows such as Law & Order: Special Victims Unit, NCIS, Rizzoli & Isles, and Greek, among others. She has showcased her versatility across various genres, proving her talent and dedication to her craft long before her high-profile marriage. Her steady work in the industry highlights a commitment to acting that she shares with her esteemed husband, creating a strong foundation for their shared life and careers.
Jon Hamm’s New Chapter: Reflecting on a Distinguished Career and Past Relationships
For Jon Hamm, this marriage to Anna Osceola marks a significant new chapter in a life already rich with professional accolades and personal experiences. Before finding love with Anna, Hamm was in a long-term, highly publicized relationship with actress and writer Jennifer Westfeldt. Their partnership spanned nearly two decades, from 1997 to 2015, making their eventual separation a notable moment in Hollywood. Hamm has often spoken about the challenges of balancing a demanding career with personal life, particularly during his tenure as Don Draper on Mad Men, a role that brought him global recognition and critical acclaim.
Following his relationship with Westfeldt, Jon Hamm was romantically linked to several other individuals. In 2019, he was reportedly seen on a few outings in the New York City area with Lindsay Shookus, a producer for Saturday Night Live who had also previously been linked to actor Ben Affleck. However, neither Hamm nor Shookus ever officially confirmed a relationship, maintaining their privacy amidst the speculative reports. These past relationships provide context to Hamm’s journey, highlighting his search for lasting partnership and underscoring the profound significance of his decision to marry Anna Osceola.
His impressive career, which includes standout performances in films like The Town, Baby Driver, and most recently, Top Gun: Maverick, has solidified his status as one of Hollywood’s most respected actors. Yet, despite his professional success, the quest for personal happiness and a committed partnership has always been evident. His marriage to Anna Osceola is a joyful affirmation of that quest, signifying a deeply personal triumph and the beginning of a new, exciting phase in his life.
A Future Full of Promise: Congratulations to the Happy Couple
The wedding of Jon Hamm and Anna Osceola is more than just a celebrity event; it’s a testament to enduring love, unexpected connections, and the beauty of shared journeys. From their initial encounter on the set of one of television’s most iconic dramas to a romantic coastal wedding surrounded by friends and family, their story resonates with many. Fans worldwide are sharing in their happiness, sending well wishes as they embark on this new adventure as husband and wife. As they settle into married life, the couple undoubtedly looks forward to a future filled with continued success, personal fulfillment, and the unwavering support of each other. Congratulations to Jon and Anna!