Michael Jackson & Madonna, Tom Cruise & Cher, Plus 5 More Celebrity Couples Who Were Actually Once Together

Besides the glitz and glam, Hollywood is also known for its star romances. Showbiz public figures have often made headlines because of their relationships through the years.

While some celebrities who worked together merely dated, others also got married. Meanwhile, there were some surprising couplings that went under the radar.

From Michael Jackson and Madonna to Tom Cruise and Cher, here are the Hollywood A-listers whose careers have also turned them into lovers, which may surprise you.

Jennifer Aniston & Paul Rudd

Jennifer Aniston and Paul Rudd met as young aspiring actors in Los Angeles. They later co-starred in the 1998 romantic comedy-drama film, “The Object of My Affection.”

During a joint interview in 2012, the longtime friends candidly discussed kissing on-screen. When asked whether they considered it weird to lock lips on-screen, Aniston answered, “Nah. I’ve kissed him for years.”

Meanwhile, Rudd, who dated Aniston’s producing partner in the ‘90s, chimed, “We’ve made out for decades.” The award-winning actress also noted, “It helps that it’s nice.”

It has been decades since Aniston and Rudd starred in the film. After she joined Instagram for the first time, the duo’s co-star Sarah Hyland posted a throwback photo from the movie.

“In honor of @jenniferaniston getting an Instagram I’m reposting this picture from almost 24 years ago. Neither she, Paul Rudd, nor myself have aged since 1996. I love ya fake mama!” the actress captioned the post in October 2019.

Madonna & Michael Jackson

Meanwhile, in a surprising revelation, two celebrated musicians shared an intimate moment once. In December 2016, Madonna appeared on “Carpool Karaoke” hosted by English comedian James Corden.

During the interview, the Queen of Pop revealed she and Michael Jackson kissed once. When Corden asked who initiated the kiss, Madonna admitted that she did, adding Jackson was shy. “However, he was a willing accomplice,” she explained.

The renowned singer-songwriter further explained that she helped the King of Pop loosen up by offering him a glass of Chardonnay. “And it did wonders,” she commented.

“The Late Late Show with James Corden” host asked Madonna whether she had told someone about this. In response, the 65-year-old actress divulged that she may have mentioned it to a friend.

Ben Affleck & Gwyneth Paltrow

From one musical icon to another’s cinematic connection, Gwyneth Paltrow dated Ben Affleck back in the day. However, her longtime friend and chef, Mario Batali, a restaurant owner, disapproved of the award-winning actor, unlike her other lovers.

The prolific businesswoman revealed in a 2016 interview that she brought every boyfriend she had to Batali’s restaurant over the years, and he did not like Affleck that much.

The actress reflected on her relationship with Affleck during her appearance on the “Call Her Daddy” podcast. She stated that although he made her laugh, they argued just as much. Paltrow also complemented Affleck, saying he was a good kisser and good in bed.

Nicole Kidman & Lenny Kravitz

Similarly, Nicole Kidman and Lenny Kravitz met through a mutual friend and dated briefly in 2003. To maintain her privacy, Kidman kept details of her relations with Kravitz under wraps. She dismissed rumors of a relationship, saying they were merely friends, yet she rented his apartment at the time.

The two were discreet as they even fooled photographers by arriving and exiting Manhattan hot spots separately. Kidman and Kravitz sparked further speculations after attending several events together.

They finally admitted that they were romantically involved at a later stage. After going public with their relationship, Kidman’s rep, Leslee Dart, said, “They’re very close. He’s very important to her.”

Following confirmation, Kravitz and Kidman eventually showed off their romance. They were spotted dining together at a party at Tavern on the Green and at magician David Copperfield’s birthday party at Tao restaurant during the same period.

One observer at Tavern on the Green revealed the duo showed affection and flirted. Another said the couple gazed at each other all night, with Kidman seated on Kravitz’s lap and massaging his leg. “They were eating off each other’s plates,” added the source.

During that period, Kidman and Kravitz were single parents. The actress was raising her daughter, Isabella, and son, Connor, from her marriage to Tom Cruise. The exes were married for ten years before divorcing in 2001.

As for Kravitz, he was raising his daughter, Zoë, whom he shares with his former wife, Lisa Bonet. Zoë had joined her dad and Kidman at Tavern on the Green. The actress reportedly was friendly with her and talked to her a lot.

A week after this outing, Kidman and Kravitz were seen alone at Copperfield’s birthday party. An insider revealed, “They held hands, whispered in each other’s ears, and were basically cheek-to-cheek the entire time. They looked like a couple.”

Kidman vaguely talked about being engaged after their romance ended. However, when asked who her fiancé was, she refused to say. The movie star explained things did not feel right at the time as they both were not ready.

“I get engaged and I get married—that’s my thing. I don’t want to date. I’m interested in a very, very deep connection,” Kidman explained. It turns out she was engaged to Kravitz for a short while. Kidman admitted this in an interview and stated she loved Kravitz because he was a good man.

Cher & Tom Cruise

Delving into another unexpected romantic flashback, in December 2013, Cher appeared on “Watch What Happens Live with Andy Cohen.” During the interview, the host asked the Oscar-winning actress to rank the best lover she has had in her list of old flames.

The iconic singer revealed Cruise ranked in the top five of her all-time best lovers’ list. In another interview, Cher spoke frankly about her connection with the “Mission Impossible” actor.

The California native divulged she and the actor formed a bond due to their shared suffering from dyslexia. By September 2018, Cher disclosed that she and Cruise were still friends.

Matthew McConaughey & Janet Jackson

Speaking of connections sparked by shared experiences, in January 2019, Matthew McConaughey appeared on “Watch What Happens Live with Andy Cohen,” with Anne Hathaway. The two actors engaged in a game called “Plead the Fifth” on the show.

While playing the game, TV host Cohen mentioned there was a rumor that McConaughey once went out with Janet Jackson. In response, the actor revealed that he had dinner with the actress. Once Cohen stated if that was it, McConaughey answered, “That’s sort of it, yeah.”

Helen Mirren & Liam Neeson

Lastly, another Hollywood pair is Helen Mirren and Liam Neeson, who dated and lived together for four years. The two first crossed paths while filming “Excalibur” in Dublin.

The A-listers appeared in a joint interview on “The Graham Norton Show” in January 2018 where they reflected on their relationship. Neeson admitted he was instantly besotted with Mirren after seeing her for the first time.

In another joint interview, Neeson and Mirren reminisced about their time together, including how they met. He starred as Sir Gawain while she portrayed Morgan le Fay in “Excalibur.”

Neeson remembered seeing Mirren as Lady Macbeth, saying, “It was mesmeric. She was so sexy. I thought, Gosh, that’s Helen Mirren!” During the interview, he could not stop raving about her beauty, adding he fell in love with her then.

After developing a romantic relationship, the Irish native moved to London to cohabit with Mirren in her flat. He found acting gigs in the British theater with Mirren’s help paving the way for him.

Neeson was a struggling actor then while Mirren received scripts daily. It became challenging for him, living under her shadow. Realizing this, Mirren decided that it was time he came out from under her wing. They decided to split despite their love for each other.

Mirren admitted it was difficult to go their separate ways. In a November 2022 interview, she said, “We loved each other. We were not meant to be together in that way, but we loved each other very, very much. I love him deeply to this day. He’s such an amazing guy.”