Can You Believe They’re Friends?! 11 Unlikely Celebrity BFFs!

Celebrity friendships are so fascinating, primarily because the most unexpected people end up becoming friends. Sometimes these friendships end up lasting decades while others fizzle fast. In memory of some of the best and worst friendships in Hollywood, here is a list of Hollywood’s 11 most unlikely celebrity friends.

11. Gwyneth Paltrow and Taylor Swift

Gwyneth Paltrow and Taylor Swift have been friends for a few years. They have been spotted posing together at events or out to dinner with the “Iron Man” star’s husband Chris Martin. It is widely believed that Paltrow set up the Grammy-winning singer with another friend of hers, Jake Gyllenhaal, but it didn’t work out.


10. Angelina Jolie and Gwen Stefani

Angelina Jolie once claimed that she didn’t really have girlfriends, but it turns out that isn’t true – she is friends with Gwen Stefani! These two have been spotted together with their children – who are actually quite close in age – having play dates. The two megastars have actually been friends since 1998.

9. Sienna Miller and P. Diddy

Back in 2007, Sienna Miller and P. Diddy were spotted together regularly at clubs and parties, sparking rumors of a romance. Both parties denied anything romantic, stating that they were involved with other people and were just really good friends. Judging by all the partying Miller did while she was in Diddy’s company, it’s probably a good thing that they’re no longer friends.

8. Ryan Gosling and Justin Timberlake

Ryan Gosling and Justin Timberlake starred on the “Mickey Mouse Club” together. Timberlake’s mother was Gosling’s guardian for six months, so the two ended up living together. They even had a crush on the same girl – Britney Spears. According to the Grammy-winning singer, these two got in a lot of trouble together when they were younger.

7. Leonardo Dicaprio and Tobey Maguire

Leonardo DiCaprio and Tobey Maguire have been friends for over 25 years. They met at an audition in the ‘80s and quickly became friends, vowing to help each other get acting gigs. Leo kept his word. When DiCaprio secured a major role on the short-lived TV comedy “Parenthood,” he convinced producers to bring Maguire on as a guest star.

6. Chris Martin and Jay Z

In spite of coming from very different backgrounds and being polar opposites musically speaking, Chris Martin and Jay Z are actually good friends. The lead singer of Coldplay described his friendship with the rap mogul to Pitchfork Magazine. “I love his music, and he’s a super cool guy, and he’s genuine. I respect his decisions, and we have the same feelings about trying to be true in your art. It just happens that one of us is a nerd and the other is the coolest multi-entrepreneur on the planet.”

5. Ed Sheeran and Courteney Cox

Ed Sheeran and Courteney Cox are an unlikely pair of friends. It turns out that the singer-songwriter introduced her to her current beau Johnny McDaid, who is a former roommate of his and the former “Friends” star let him stay at her beach house and invited him to Thanksgiving at her place. Cute!

4. Robin Thicke and Leonardo DiCaprio

Who knew that Robin Thicke and Leonardo DiCaprio were close pals! The Oscar-nominated actor was one of the men spotted at the “Blurred Lines” singer’s birthday party and, back in January, these two were spotted on a bender after the “Wolf of Wall Street” London premiere.

3. Jessica Chastain and Michelle Williams

Jessica Chastain and Michelle Williams have been friends for years. Before they were famous, these two roomed together when they appeared in a summer stock production of Anton Chekhov’s “The Cherry Orchard.” According to Chastain, they developed a bond like sisters and have been super close ever since.

2. Paris Hilton and Brooke Mueller

It is hard to believe that Paris Hilton and Brooke Mueller were ever friends. “The Simple Life” star is a notorious party girl and Charlie Sheen’s ex wife is a recovering addict, so that alone would be enough to deter these two from hanging out but, if you have ever watched “The World According to Paris,” then you would know that these two were BFFs at one point.

1. Lindsay Lohan and Kate Moss

Lindsay Lohan and Kate Moss were inseparable back in 2005 and 2006. These two were spotted out together at clubs, parties, strip joints and on vacation. Moss was reportedly helping the troubled star deal with the pressures of being famous but, with their respective histories of alleged drug use, the friendship probably wasn’t good for either of them.