Working alongside Leonardo DiCaprio is a dream come true for most actors. Take Jonah Hill as an example, he appeared alongside Leo in The Wolf of Wall Street – not only did he thrive in the spot but the two also developed a close relationship alongside one another.
Throughout the article, we’ll get some unique takes on what it is like to be with Leo, both on a professional level, along with in a dating relationship. Despite some of his breakups, some have nothing but kind words about the actor – while some like Gisele, as we’ll see throughout the article took a different approach when reflecting on their time together. We’ll feature so many other celebs including Brad Pitt and George Clooney, their words might surprise you!
Without further ado, here’s what these celebs have said at Leonardo DiCaprio, both good and bad. Enjoy, let’s get started!
11 George Clooney – It’s Is Important To Have Someone In Your Life To Tell You What Is What
George Clooney took a subtle shot at the Hollywood megastar, making the claim that his entourage is constantly pumping his tires. Clooney recalled a pickup basketball game against Leo and his boys, despite the hype around DiCaprio’s game, Clooney wasn’t impressed. He discussed the experience with E Online;
“The discrepancy between their game and how they talked about their game made me think of how important it is to have someone in your life to tell you what's what. I'm not sure if Leo has someone like that."
10 Nina Agdal – “He Loves All The Attention He Gets From Women”
The media was surprised at how affectionate Leo was in public during his time alongside Nina Agdal. Despite the close connection, it was another relationship that just would not last.
According to a source with People, it is going to take something for special to finally settle the celeb down for good. The source also noted that he just loves getting attention from women in general, hence all the changes in partners over the years.
9 Jamie Foxx – “He Comes In So Different”
These two would become close friends – it all started during their time together in Django Unchained. Foxx admittingly didn’t know what to expect prior to meeting Leo, as he had a different perception thanks to the tabloids. As he stated with Vanity Fair, the real Leo was much different;
“Here comes Leonardo DiCaprio, the good-looking guy that you see in the tabloids with the models. And he comes in so different and ready to work—to see those guys get together in the corner and develop the character and watch the character go different ways.”
8 Gisele Bundchen – “I Was Alone In Doing Some Serious Soul-Searching”
Gisele hasn’t pulled any punches when assessing her time alongside Leonardo DiCaprio. Although most of her thoughts are positive – she did admit that for certain things, she turned a blind eye. Once the realization hit, Leo wasn’t willing to take the same honest look at himself;
“I was becoming more and more aware of things that I’d chosen not to look at. Was I alone in wanting to do some serious soul-searching while he stayed the same? In the end, unfortunately, the answer was yes.”
7 Michael Jordan – “All For One And One For All”
Leo was already sniffing in Hollywood icon territory during the ‘90s. He was making several close connections – one with the face of sports in the ‘90s, Michael Jordan.
As we recently saw in The Last Dance, Leo was present for the festivities out in the locker room. MJ would even reference Leo’s line from The Man in the Iron Mask – Jordan uttered the line to his teammates, "all for one and one for all.”
6 Jonah Hill – “He Gave Me The Best Advice”
It was a career-changing moment for Jonah Hill as he took part in the Wolf On Wallstreet. Not only did he thrive in the spot but he would also develop a close relationship with Leonardo DiCaprio during the process. Of course, as most do, Hill would ask Leo for some advice – according to People, here’s what Leo had to say;
“Leonardo DiCaprio, he gave me advice: Always meet them if you can and take what you want and leave what you don’t. I really think it’s great if you can for that reason.”
5 Brad Pitt – “I Had A Restraining Order Against Leo For A While”
Pitt added some fuel to the fire, perhaps jokingly, we’ll never really know. Pitt made mention that he put a restraining order on DiCaprio back in the ‘90s. That might’ve had something to do with his relationship alongside Gwyneth Paltrow, as the two broke off the engagement in ’97 and she was seen with Leo shortly after;
“Yeah, I had a restraining order against [DiCaprio] for a while… over an incident in 1994 that we don’t like to talk about.”
4 Margot Robbie – “He’s A Down To Earth Person”
Robbie worked alongside Leo during The Wolf On Wall Street – she also had the nerve-racking moment of having to completely disrobe in front of the actor. Despite the moment, she was thankful to have worked alongside Leo – she was also surprised by how humble he is;
“He’s an incredible actor, everyone knows that, but he’s also a really awesome down to earth person so it was a really lovely experience. I was very fortunate.”
3 Kasi Brown – “He Likes To Share Stories And Life Experiences With People."
This is a unique take shared by Leo’s personal assistant of a few years, Kasi Brown. She explained with College Times that the two had a playful relationship and that Leo always kept things light around her and everyone else. She also recalls DiCaprio sharing lots of stories from his past;
"He’s extremely down to earth and he likes to share stories and life experiences with people."
2 Erin Heatherton – “He Is A Wonderful Person”
“'He's a wonderful person and he's a friend of mine, I wish him all the best. I've never had a boyfriend I've been more comfortable with and more at one with now. 'I've never lived with someone before. I'm very lucky, I'm very loved and feel very content. I guess love does that.”
As it turns out, Leo leaves a good impression with his exes as well, that at least the case with Erin Heatherton, who remains on good terms with Leo despite the separation, according to her words with AZ Central.
1 Kate Winslet – “It Is Like Family”
Although the media and fans would love these two to share a real-life romance, as they depicted in Titan, Winslet admitted with Elle that their bond is more so family-like, as they remain closer than ever;
“I do feel so grateful for that friendship, and honestly it is like family and one of those rare Hollywood friendships that I feel very, very blessed to have."
Sources – People, Vanity Fair, E Online & College Times
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