A-List Celeb Reopens Hillary Clinton's Old Wounds With New Info About Bill's Cheating Past

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Back in the late 90s, Bill Clinton's affair with Monica Lewinsky dominated the news cycle. Bill was in his second presidential term at the time, and his behavior was also under discussion as part of impeachment proceedings. For Lewinsky, the affair created long-lasting trauma, while Bill was acquitted with minor dings to his presidential reputation. Hillary Clinton was fortunate to have friends to lean on during the affair's exposure. She also remarked on emotional burden, telling Ellen DeGeneres in 2020, "staying in my marriage was the gutsiest personal decision I ever made."

Although it's all far in the past, Hillary's old wounds continue to be reopened. Sometimes it's a deliberate decision on her part, like when she discussed the incident in the Hulu docuseries, "Hillary." Now, however, the blow is coming unexpectedly from Charlie Sheen's 2025 memoir, "The Book of Sheen," where he chronicles meeting Bill. It was the late 1980s, and rather than being star-struck by the young actor, Bill was purportedly more captivated by Dolly Fox, Sheen's then-girlfriend.

One of Sheen's castmates asserted that Bill wanted to know more about Fox. However, the then-Arkansas governor apparently didn't take any action beyond this not-so-discrete inquiry. Even so, the encounter left a lasting impression on Sheen. "I felt bad for Dolly to be objectified and skeeved-out like that, but still had to take some pride in 'Bubba' fancying my gal," Sheen wrote decades later (via People). "To her credit, she laughed and was actually flattered."

Charlie Sheen has long been convinced that he was an important early witness to some of Bill Clinton's inappropriate behavior. Amid the dramatic coverage of Bill's affair with Monica Lewinsky, the actor was disappointed that people didn't see the same significance as he did. Even so, he's preserved, touting the parallel while promoting his memoir. "We were ringside," Sheen declared to Jesse Watters on Fox News in September 2025.

However, Bill had a far more scandalous incident happen in the early 90s involving Paula Jones. She accused Bill of sexual harassment, and the legal proceedings lasted from 1994 to 1998, overlapping with the Lewinsky scandal. Although Bill denied Jones' accusations, he did agree to pay a hefty settlement. While mentions of this incident occasionally crop up, they don't appear to cause the same pain for Hillary as the Lewinsky affair.

In that case, part of the trauma may stem from how Bill communicated with his wife. In the Hulu docuseries, "Hillary," the former first lady recalled how her husband denied the affair when he first broached the topic. Months later, Bill changed his story, and the reversal was particularly wrenching for Hillary. "I was just devastated," she explained (via Newsweek). "I was just so personally hurt and, 'I can't believe this. I can't believe you lied.'" This emotional wound, coupled with the fact that Hillary didn't decide to divorce Bill, is one thing people find particularly weird about the former first couple's marriage.