Inside The Rumors Ashley Judd And Michael Bolton Once Dated

Although she's 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 achieved widespread recognition and high praise as the titular lead in Victor Nunez's 1993 film, "Ruby in Paradise," Judd went on to receive critical acclaim for her portrayal of a fictionalized Marilyn Monroe in the HBO film, "Norma Jean & Marilyn" in 1996, acquiring both Golden Globe and Primetime Emmy nominations.

Judd's also known for her outspoken activism, which even led Judd to consider a U.S. Senate run in her home state of Kentucky in 2014 — a run which she did not end up taking. She later became a vocal critic of former President Donald Trump, and endorsed and campaigned for Massachusetts Sen. Elizabeth Warren for president in 2020. 

Considering Judd's larger-than-life presence both onscreen and offscreen, fans may be inclined to wonder what the deal is with her love life. The truth is that Judd has been involved in a few notable romances, apparently including one with singer Michael Bolton back in the '90s. Although the romance between two appears to have been quite brief, it seemed to have a pretty 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 starkly 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 seem to have actually dated for a few years back in the '90s. Although the exact timeline is fuzzy, it's fair to suspect something was going on when Judd starred as the female lead in Bolton's 1997 sultry music video for "The Best of Love," a song which he co-wrote. "All I'm askin' is to keep you near forever, just 'till the end of time," Bolton sang, evidently to Judd. "My heart is overflowing ... I wanna spend my time, spendin' time with you, baby." 

Judd seemed to have been crazy for him in return, too. "I'm so swept 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 Spokesman-Review). "I'm not really conscious of anybody but him." Judd even called him "family," adding that he was "very sweet," according to Glamour.

Though the video — and lyrics — were rather suggestive, their relationship would not last until the end of time. While it's unclear exactly when they broke up, it's safe to say it happened sometime before the turn of the century, as Judd met her future husband, British race car driver Dario Franchitti, in 1999, per The Sun.

Michael Bolton later performed with Ashley Judd's half-sister

Given the heartwarming bond Ashley Judd and Michael Bolton seemed to have shared while together, it is unsurprising that they remained close friends despite their breakup, according to Glamour

Ashley Judd is also not the only member of the Judd family with whom Bolton has been involved in one way or another, 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 for being 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 off their chemistry, with Wynonna justifying their "strange combination" by saying that she and her other big touring partner — her mother, Naomi — also made for a "strange" pairing. "So it seems natural," she said of herself and Bolton. Bolton, for his part, declared, "I love the Judd women." Despite the fact that there has been no indication of any romantic link between Bolton and Wynonna, they nonetheless made for a dynamic musical pairing, and there is no doubt that Bolton and the Judds certainly run deep.