Charlie Sheen recalls memorable encounter with Bill Clinton during recent television appearance

 September 12, 2025

During a recent television interview, actor Charlie Sheen shared an intriguing interaction with former President Bill Clinton that involved a humorous inquiry about Sheen's girlfriend at the time, as Breitbart reports.

Sheen narrated the light-hearted anecdote from a past public event in which Clinton showed interest in Sheen's then-girlfriend, Dolly.

The retelling unfolded on Jesse Watters Primetime on the Fox News Channel, where Sheen reminisced about his colorful past, including his meetings with various celebrities and prominent figures.

Clinton's gift to Sheen

Sheen described how he first met Bill Clinton at a press event. The former president gifted Sheen a pair of Razorback shoes, which Sheen humorously commented were particularly tacky and colored bright red.

"It was a press event. He gave me the Razorback shoes, and you’ve probably seen them. They’re like, really tacky and red," recounted Sheen during the interview.

He added that the shoes were given in jest, highlighting Clinton's sense of humor, "But he gave them as a joke," Sheen clarified.

Unexpected inquiry unfolds

Following the light-hearted moment shared over the red shoes, the encounter took a comical turn when Clinton showed a sudden interest in Sheen's companion. The former president discreetly asked an aide for more information about Sheen's brunette girlfriend.

"And then as we’re moving away from the stage, Alan hears him whisper to one of his aides, tell me what you can about the brunette, right?" Sheen shared, identifying his girlfriend as Dolly.

This private inquiry did not remain a secret for long, as Sheen and Dolly were soon informed. They subsequently found the episode quite amusing and flattering.

Presidential scandal referenced

Charlie Sheen recounted telling the funny story to Dolly later that day at a bar, where they both appreciated the light-hearted attention from Clinton. "And the brunette was my girlfriend, and so we had a laugh about it, and her name’s Dolly, and we told her about it in the bar later on, and she was really flattered," he explained.

The incident was briefly connected to Clinton's involvement in the Monica Lewinsky scandal during the televised conversation between Sheen and Watters. The scandal, notorious in its own right, added a layer of irony to the past encounter.

"And then later on, the whole thing happens, you know. Yes, the whole thing— Lewinsky! Yes, yes! We know. And it was like, OK, hold on, man. We were -- we were ringside," stated Sheen, encapsulating the surreal nature of his experiences and associations.

Sheen's bizarre Hollywood journey

The interview provided audiences a glimpse into Sheen’s past associations with high-profile figures and the unlikely yet memorable encounters he experienced during his turbulent career in Hollywood.

From receiving peculiar gifts to humorous exchanges with a future president, Sheen's recountings offered a unique perspective on the interwoven lives of celebrities and political figures.

As a recovering addict, Sheen's new revelations on television have captivated viewers, offering both entertainment and insights into the complexities of relationships and fame.

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