Kevin Costner has reportedly been quietly pursuing Demi Moore for several months. The acclaimed “Yellowstone” star was among the first to offer comfort to Moore after her surprising loss at the recent Academy Awards. Despite winning both the Golden Globe and SAG awards for Best Actress, the 62-year-old actress ultimately lost the coveted Oscar to 26-year-old Mikey Madison.

The 70-year-old “Dances With Wolves” star, who is currently single and open to new relationships, reportedly didn’t hesitate to lend a supportive shoulder to Moore, according to an insider. “It’s clear that losing to someone less than half her age was tough for Demi,” the source suggests. “Kevin has been making an effort to remind her that she remains one of the most stunning women in Hollywood, though he definitely has a personal interest.”

The two have apparently been exchanging flirtatious signals for some time. “Kevin is trying to be a true gentleman, cheering Demi on and encouraging her not to give up. He genuinely believes in her talent and thinks she’ll have another shot at the Oscar,” the insider adds. Costner and Moore have been friends for decades, ever since they both auditioned for “Flashdance” back in 1983, though neither ultimately landed the role. Their connection grew stronger after co-starring in the 2007 thriller “Mr. Brooks.” “Nothing romantic happened back then, but Kevin was clearly impressed by her. Whenever her name comes up, he speaks highly of her,” the source shares.

Now, Costner is reportedly turning to longtime friend Billy Bob Thornton, who co-stars with Moore on the series “Landman,” for a little help in winning her heart. “Billy Bob has been close to Demi for years, so he’s the perfect ally to support Kevin’s efforts. He’s been encouraging Kevin to make a move for quite some time,” the insider reveals. “Ultimately, it’s Demi’s decision whether to take things further, but friends think she should consider it.” Adding further fuel to Costner’s motivation is the recent engagement of his ex-wife Christine Baumgartner to financier Josh Connor, who was once a friend of Costner’s. “Kevin’s partly driven by a desire for some payback, and he’s sure Christine would be jealous to see Demi by his side,” the source confesses. “But that’s not the only reason he’s interested — though it would definitely be an added bonus!”

While Costner’s personal life continues to capture headlines, his professional legacy remains deeply intertwined with his monumental portrayal of John Dutton in Taylor Sheridan’s acclaimed neo-western drama, “Yellowstone.” For millions of viewers, Costner is no longer just the iconic star of “Dances With Wolves” or “Field of Dreams,” but the stoic, fiercely protective patriarch of the Yellowstone Dutton Ranch. His role as John Dutton has not only revitalized his career but also cemented “Yellowstone” as a cultural phenomenon, redefining the modern Western genre for a new generation. The intensity and authenticity he brought to the character resonate deeply, reminding audiences of the enduring power of land, family, and tradition in the face of relentless modern challenges.

“Yellowstone” burst onto the scene in 2018, quickly establishing itself as a ratings powerhouse for Paramount Network. Its gritty realism, complex characters, and breathtaking Montana landscapes struck a chord, particularly with audiences in the American heartland. At its core, the series explores the Dutton family’s relentless struggle to defend their ancestral ranch, the largest in the United States, from various threats: land developers, an adjacent Native American reservation, and political adversaries. John Dutton is the quintessential American patriarch – a man of unwavering principles, often ruthless in his methods, driven by an unshakeable commitment to his land and legacy.

Costner’s portrayal of Dutton is central to the show’s appeal. He imbues the character with a gravitas born from years of navigating Hollywood’s highs and lows, echoing the character’s own battles. Dutton is a man constantly battling personal tragedies—the loss of his wife, the complicated relationships with his children—while simultaneously fighting existential threats to his way of life. Costner masterfully conveys Dutton’s inner turmoil: the burden of responsibility, the moments of profound loneliness, and the flicker of tenderness beneath a hardened exterior. He is a character caught between preserving a vanishing past and adapting to an encroaching future, a conflict that resonates with many in contemporary society.

The show masterfully weaves together themes of land ownership, environmentalism, indigenous rights, and the corrupting influence of power. It delves into the moral ambiguities of its characters, depicting a world where right and wrong are rarely clear-cut. John Dutton, despite his often questionable actions, is seen by many as a symbol of integrity and resilience, a man willing to sacrifice everything for what he believes in. This complex heroism is a hallmark of Costner’s career, often playing characters who stand alone against overwhelming odds. His deep understanding of the Western archetype, cultivated through films like “Silverado” and “Open Range,” made him the ideal choice to bring John Dutton to life.

Costner’s commitment to the role and the series was initially unwavering, driving “Yellowstone” to unprecedented success. His performance earned him a Golden Globe Award for Best Actor in a Television Series Drama in 2023, a testament to his impact. However, the actor’s journey with the series has been tumultuous in recent seasons. Reports of scheduling conflicts, particularly with his ambitious multi-part Western film saga “Horizon,” led to his eventual departure from the flagship show. This highly publicized exit has left a significant void in the “Yellowstone” narrative, prompting questions about the future of the series and the iconic Dutton family without its central figure. The departure underscores the challenges of balancing a demanding television schedule with major film projects, even for a seasoned veteran like Costner. For fans, the idea of “Yellowstone” without John Dutton is almost unthinkable, a testament to how deeply Costner’s portrayal resonated. His presence lent an authentic weight to the narrative, grounding the sprawling saga in a relatable, albeit larger-than-life, human struggle.

Ultimately, Kevin Costner remains a compelling figure in Hollywood, whether he’s navigating a blossoming new romance or commanding the screen as a ranching patriarch. His continued relevance, from gossip columns to critical acclaim, speaks to a career built on a unique blend of rugged individualism and profound dramatic depth. As he embarks on new personal chapters and continues to shape his creative legacy with projects like “Horizon,” the shadow of John Dutton and the vast landscapes of “Yellowstone” will undoubtedly remain a defining chapter in his remarkable career, a testament to an actor who consistently brings gravitas and authenticity to his roles, both on and off the screen.