Inside the Rumors Ashley Judd and Michael Bolton Ever Dated

While not a member of her mother and sister’s famous country music duo, Hollywood superstar Ashley Judd has made quite a name for herself in the entertainment industry. After she first gained wide recognition and much praise as the titular lead in Victor Nunez’s 1993 film, “Ruby in Paradise,” Judd received critical acclaim for her portrayal of a fictional Marilyn Monroe in the 1996 HBO film “Norma Jean & Marilyn,” and acquired both golden Globe and Primetime Emmy nominations.

Judd is also known for her outspoken activism, which even prompted Judd to consider a US Senate round in her home state of Kentucky in 2014 — a run she ultimately didn’t take. She later became a vocal critic of former President Donald Trump, and endorsed and campaigned for Massachusetts Sen. Elizabeth Warren running for president in 2020.

Given Judd’s larger-than-life presence both on-screen and off, fans might be tempted to wonder what the deal is with her love life. The truth is that Judd has been involved in a few notable romances, including apparently one with singer Michael Bolton in the ’90s. Although the romance between the two seems to have been quite short, it seemed to have quite a big impact on both of their lives.

Ashley Judd starred in Michael Bolton’s steamy 1997 music video

Despite the 15-year age difference and the vastly different backgrounds between Michael Bolton – a jewish soft rock star from Connecticut – and Ashley Judd – a Hollywood actor who comes from a family of country music stars – the two appear to have dated a few years ago in the ’90s. While the exact timeline is vague, it’s fair to suspect something was going on when Judd played the female lead in Bolton’s sultry music video for “The Best of Love,” a song he co-wrote. “All I ask is to keep you with you forever, just until the end of time,” Bolton sang, apparently to Judd. “My heart is over… I want to spend my time, time with you, honey.”

Judd, in return, seemed to have been fond of him, too. “I’m so carried away that, as far as I’m concerned, the rest of the world doesn’t exist,” Judd told Harper’s Bazaar in 1997 (via The Spokesperson Review† “I’m not aware of anyone but him.” Judd even called him “family,” adding that he was “very sweet,” according to glamour

While the video — and lyrics — were quite suggestive, their relationship wouldn’t last until the end of time. While it’s unclear exactly when they broke up, we can safely say it happened sometime before the turn of the century, when Judd met her future husband, British racing driver Dario Franchitti, in 1999. The sun

Michael Bolton later performed with Ashley Judd .’s half-sister

Given the heartwarming bond that Ashley Judd and Michael Bolton seemed to have had while they were together, it’s not surprising that they remained good friends despite their breakup. glamour

Ashley Judd isn’t the only member of the Judd family that Bolton has somehow interacted with, either. In 1998, shortly after the end of his relationship with Ashley Judd, Bolton went on tour with her older half-sister, Wynonna Judd, widely known at the time as one half of the country music duo The Judds, along with her mother, Naomi.

In a 1998 interview with The Nashville Network, Wynonna and Bolton showed their chemistry, with Wynonna justifying their “strange combination” by saying that she and her other major travel partner — her mother, Naomi — also made for a “strange” combination. “So it seems natural,” she said of herself and Bolton. Bolton, for his part, stated, “I like the Judd women.” Despite the fact that there is no indication of a romantic bond between Bolton and Wynonna, they nevertheless made a dynamic musical couplingand there’s no doubt that Bolton and the Judds certainly go deep.

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