Kylie and Timothée got your head in a spin? Here are 12 of Hollywood’s strangest couplings
Eric André & Emily Ratajkowski
We’ve all seen the Valentine’s Day post by now, which alerted us to the situationship between Ratajkowski and André in late 2022. She is rumoured to now be seeing Harry Styles, but a part of our heart is still with André and what could have been.
Tupac & Madonna
Iconic much? During a 2015 interview with Howard Stern, the ‘Like a Virgin’ megastar revealed she once dated rapper Tupac Shakur for two years between 1993 and ‘95. There is even an alleged unreleased track from the two, which Madonna revealed she may one day release to honour his legacy…
Liam Neeson & Helen Mirren
Rather a random pairing but it makes sense when you consider that they met on the set of Excalibur in 1980. They kept things going for four years, with Neeson telling CBS, “Oh, my God. Can you imagine riding horses in shiny suits of armour, having sword fights and stuff, and you’re falling in love with Helen Mirren? It doesn’t get any better than that.” No, it doesn’t Neeson.
Elon Musk & Grimes
An obvious one but it still makes us WTF when we take a step back and reevaluate how alt-princess Grimes and Tesla CEO Elon Musk got together. What did they talk about? Did he like her music? Does she drive a Tesla still? Guess we will have to wait until their baby X Æ A-12 Musk is old enough to reveal all about their parent’s romance. The pair did face a rough breakup in 2021 though, and not even their cringe-fest Twitter posts could save them.
Jared Leto & Cameron Diaz
Super hot Hollywood couple Diaz and Leto dated in the early 00s and despite an effort to keep their relationship under wraps, they quickly became the talk of the tabloids. The pair were together for four years from 1999 until 2003, but they never really publicly spoke about what happened between them.
Macaulay Culkin & Mila Kunis
Yep, Home Alone child star Culkin and That 70s Show icon Kunis were together for a whopping 9 years between 2002 and 2001. They were super lowkey, and though the breakup was “horrible” according to Kunis on the Armchair Podcast with Dax Shepherd in 2018, she later married her co-star Ashton Kutcher and Culkin the Disney channel star Brenda Song. It all worked out in the end.
Matthew McConaughey & Janet Jackson
Okay fair enough – *dating* is not confirmed, but the rumours are rather juicy. The two reportedly had a fling after meeting at the 2002 Grammys. Jackson has hinted that it was all true to Upscale Magazine in 2006, while McConaughey has said that they regularly swapped music and were just friends to Andy Cohen. Maybe we will never really know…
Ryan Gosling & Sandra Bullock
He may be famed for his relationship with Rachel McAdams, but Gosling actually dated Bullock in 2002 when co-starring in the film Murder by Numbers. Bullock was 16 years older than him at the time, and the relationship was less than two years. Gosling labelled himself the “bad guy” to Us magazine and reportedly left Bullock heartbroken.
50 Cent & Chelsea Handler
The hip-hop mogul and comedian dated for a few months in 2010. Handler told Oprah Winfrey that “it wasn’t the most serious relationship. He came on my show [in 2010] and he sent me flowers. And I was like, ‘I’m not gonna date somebody whose name is a number.” Regardless, she still labels him as her “favourite ex”.
Tom Cruise & Cher
An iconic 80s fling to remember, to say the least. The blockbuster actor and musician were revealed to have been together when Cher told Andy Cohen that Cruise was one of her “top-five” favourite lovers ever. Go Tom!
Lenny Kravitz & Nicole Kidman
Gone but never forgotten. It must have been an iconic pop culture moment when singer Kravitz got with the ultimate ‘American Woman’ (get it?) in 2003 until 2005. The pair were even engaged, but eventually called it quits. Kidman went on to star in the TV series Big Little Lies with his daughter Zoë Kravitz, who told The Edit that she remembers how Kidman “would take me to see movies; she was so nice to me.”
Gerard Butler & Brandi Glanville
If you watch Real Housewives of Beverly Hills, you will know Brandi Glanville is a name to remember. And actor Gerard Butler clearly felt the same way, as he admitted to Andy Cohen in 2013 that despite forgetting her name “she was wild”. He added that “it was a one-afternooner, but it was fun.”
