20 Hollywood BFFs Fans Would Be Surprised To See Together

It’s odd to think about how some of the greatest bonds in our lives can come from some of the most surprising places. Life-long friendships can come from chance encounters and from unexpected places. Some friends have almost nothing in common, except for their ability to connect on a personal level. And those are sometimes the most powerful friendships — the ones you don’t expect. Take these celebs for example, who have found common ground with all sorts of fellow celebrities. While we judge celebrities based on the limited information we have of them, the truth is that our favorite Hollywood celebrities have their own inner and private lives that most people will never understand.

Some of these stars were potentially rivals but became close instead. Others were just as taken aback by the unexpected bond as we are, but love it all the same. And some just defy all rhyme and reason, but hey, friendship transcends expectations. We’re excited to see all these stars actually getting the chance to step out of the spotlight and just hang out with a buddy, even if the pairings can be surprising to know continue from off-screen and into real life. Here are 15 surprising celebrity BFFs.

20 Martha Stewart and Snoop Dogg

via: Channel24

Martha Stewart spent decades as one of the most powerful women in America, and she has risen back in influence since her incarceration for multiple financial crimes. She bounced back strong, resuming her famous show, Martha, and continuing to usher in new guests. In 2008, one of those guests was the rapper, Snoop Dogg. The two got along surprisingly well, with Martha later commenting on his fun it was to talk with the Snoop. He reappeared on her show, and the two reconnected during the 2015 roast of Justin Bieber, of all people. They have since taken to appearing on game shows together and have used their natural chemistry to bring together a cooking show for VH1.

The two have nothing but good things to say about one another too, which is incredibly sweet. Stewart considers him to be an incredibly funny guy (and a pretty good cook), while Snoop Dogg told the Rolling Stone that “When we come together, it’s a natural combination of love, peace, and harmony.”

The two have become incredibly reliant on each other, with Stewart telling People, “When you work with someone like Snoop, it’s like having a sidekick. How great it is. That’s why all the comedians have sidekicks and bands because it loosens them up and lets them be freer. Snoop is my freedom.”

19 Leonardo DiCaprio and Tobey Macguire

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Leonardo DiCaprio is one of the biggest stars in the world and has been since he was a teenager. He’s been an undisputed icon for years and has been doing anything he wants with anyone he wants. But it might surprise you to learn that a frequent partner of his during these adventures is the original Spider-Man himself, Tobey Macguire. The pair has actually been friends for over 30 years by this point, meeting one another at an audition when they were both 12.

The two even arranged it so they were neighbors at one point, probably as an excuse to just hang out more. The two eventually appeared together in The Great Gatsby, which mined some of their natural charm together on-screen for one of the central friendships of the story.

Their bond has been well-documented, with the two actors often going on vacations together and even going big on some luxury yacht trips. DiCaprio is even considered a member of the family by Tobey, to the point where his children consider him their Uncle Leo. Tobey told People, “They will visit the beach, or grab Sunday brunch. Leo is great with Ruby and Otis… He is very hands-on too, and offers help with cutting up their food and will carry them across the street. He would be a great dad!"

18 Natalie Portman and Rashida Jones

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Natalie Portman is one of the most talented actresses in Hollywood, consistently working since her childhood in everything from indie dramas to action tragedies to sci-fi epics. But even she had to deal with the downsides of the industry she chose. While she famously had some difficulty getting her career back on track following the poor reception of the Star Wars prequels, Portman recently spoke about a difficulty in her industry to meet women on-set.

In light of the #MeToo movement, Portman has been speaking out in support of her fellow actresses and described how the event kept her from befriending many of the women she worked with.

Portman revealed, “It’s been really incredible to gather actresses because I think something that we realized was that we’re usually the only woman at work… So, like many other industries, we walk onto a nearly all-male set and we’re usually alone and we rarely get to interact with each other. I’ve never had—I think Rashida was my only close actress friend until now.” Rashida Jones feels the same way, describing Portman to Marie Claire by saying she “…would fight beasts 10 times her size to protect the people she loves. She is the kind of friend who can sub in and love you through the times when you can't necessarily love yourself."

17 Michelle Williams and Busy Phillips

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Dawson’s Creek stands out amongst the teen dramas of the 1990's, partly thanks to memes of the series that became a big thing online, but also due to the surprisingly deep cast of actors and actresses the series gave us. Beyond Katie Holmes and James Van Der Beek, the show also produced a real life friendship between Michelle Williams and Busy Phillips. Vulture has even put together a timeline of their friendship together, plotting out these two best friends over the years.

The two met when Phillips was added to the show following the (premature) cancelation of her other series, Freaks and Geeks. The two became fast friends, and stayed as such, even when Williams married Heath Ledger.

Busy was even named the godmother of their daughter, Matilda (alongside Jake Gyllenhaal, who was named the godfather), in 2005. Busy and Williams’ mother were even the two people who immediately came to Michelle’s side in the aftermath of Heath Ledger’s tragic passing. The two have been incredibly supportive of each other ever since, being each other’s guests for awards ceremonies. Michelle even went on to personally thank Busy in her Golden Globe acceptance speech.

16 Angelina Jolie and Gwen Stefani

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Angelina Jolie was one of the biggest actresses in the world, who has shifted in her career away from appearing on-screen towards directing and charitable works. It’s a commendable shift, especially when she’s had to deal with major personal changes. Her high-profile divorce from Brad Pitt understandably seemed to suck up her life in 2016, but she had the good fortune of having a close friend to help her through these problems. But, surprisingly enough, it’s not another highly respected actress or dignitary who proved to be her confidant. No, according to Hollywood Life, it’s the "Holla Back" girl herself, Gwen Stefani.

Before she went through a divorce herself, Stefani had met Jolie and bonded with the actress after both gave birth just a few days apart in 2011. The two remained close through the years, and proved to be stable friends that they could rely on. Their children have also become close, setting up play dates on the regular that the mothers get to take advantage of, too. And following the divorce, it’s clear that Jolie went to Stefani for help. Jolie ended up hiring the same lawyer that represented Stefani in her public split from Gavin Rossdale in 2015, taking that advice to heart.

15 George Clooney and Brad Pitt

via: PaperMag

Speaking of Angelina Jolie’s ex, let’s take a look at one of the most important (and pretty) friendships of her now former husband, Brad Pitt. Namely, the one that’s grown between himself and fellow member of Hollywood royalty, George Clooney. Becoming friends in 2001, while co-starring in Ocean’s Eleven, the two hit it off. The chemistry between them and the rest of the cast helped usher in two following movies, and established a long standing friendship between the two. There’s even a childish innocence to it, with the two engaging in a decades long prank war with one another and Matt Damon.

Although rumors surfaced that things grew rough between the pair when there was friction between their respective wives, Clooney proved to be a loyal friend when Jolie and Pitt divorced.

According to the Mirror, Pitt and Clooney reconnected following the split, with Clooney reportedly being the grounded force that kept Pitt from going off the deep end. Pitt has since given up alcohol (which apparently played a role in his break up with Jolie), and it’s easy to see how Clooney’s influence might have helped with that. Pitt has even taken to flying directly to Clooney’s house, just for the chance to see his two twin daughters.

14 Zach Braff and Harry Styles

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Zach Braff first grew in notoriety when he starred in the 2000's medical sitcom, Scrubs. It was a fun show that was willing to get surprisingly and effectively dramatic when it wanted to, and Braff used the success of the show to further his film career with movies like Garden State. Braff has become a frequent user of Kickstarter to fund his films, and ended up bringing an unexpected guest with him to premiere his film, Wish I Was Here, at the Sundance Film Festival. Arriving to support his friend was Harry Styles, the One Direction singer and icon to an entire generation of women.

The two have become friendly through Twitter. Braff realized that Styles was actually following him on the website already, and sent him a message. The two evolved from online acquaintances into real life buddies very quickly. The two even went out of their way to set up a bit of a man date during his national tour in 2013. The two kept hanging out, and Braff has noticed the effect it’s had on his Twitter page. As reported by the Mirror, Braff, at one point, tweeted out “So I'd like to thank Harry for following me because I got like a zillion 12 year olds who love me too. They think that me and Harry are hanging out together, going out on the town."

13 Drew Barrymore and Ellen Page

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Drew Barrymore and Ellen Page first met on the set of Whip It!, the 2009 roller-derby comedy starring the two. The meeting actually proved to be more important to both actresses than just meeting a new friend, as evidenced by the way the two acted during a number of interviews. They could barely keep their hands off each other during the interview, while Barrymore wore a homemade scarf that Page had knitted for her. During the interview with Marie Claire, Barrymore admitted that the younger actress had actually inspired her during the course of filming to feel better about herself.

She said, “Ellen has such a beautiful body, and I personally battled with my own body image for years. I used to tell myself, you can't wear anything sleeveless or strapless. And all of a sudden I was like, What if I just didn't send such negative messages to my brain and said, wear it and enjoy it? And now I'm more comfortable in clothes than ever.” The two were so close, that when Ellen Page came out in 2014 and revealed to the world at large that she was a lesbian, eyes turned back to their earlier interactions and even wonder if the two were closer than just friends.

12 Miley Cyrus and Kelly Osbourne

via: Miley Maniacs

Miley Cyrus and Kelly Osbourne actually share a great deal in common. Both are the daughters of high-profile singers (Billy Ray Cyrus and Ozzy Osbourne, respectively), and the two appeared together in the direct-to-DVD 2012 film, So Undercover. Ironically enough, the film seemed to come as a last gasp for her Disney channel period of her career, and her ensuing appearance and style came at the same time that she befriend the former MTV reality star. Since then, the two have been spotted together at a number of events, partying it up.

As reported by the Huffington Post, Kelly spoke to Caitlyn Becker about Cyrus and said, “I’m proud of her because whether you agree with what she does or not, she stands by her guns and she’s not fake.” Osbourne has proven to be the kind of friend who can riff on her buddies, even teasing Miley in videos from a birthday party for the singer. The two seem like a perfect match, having each other’s backs during Halloween or just finding one another any whatever event they have to put up with this week. And we’re glad to see that both of these young women (neither of whom are strangers to drama) have found someone they can relate to.

11 Jack McBrayer and Alexander Skarsgard

via: Bravo TV

This might be one of the most unlikely friendships on this list, and that’s saying something when we started with Snopp Dogg and Martha Stewart. But it’s true, the adorably southern, Jack McBrayer (who famously played Kenneth Parcel in 30 Rock), and Alexander Skarsgård (who caught the attention of everyone on the planet on True Blood) are actually extremely tight buddies, according to Hello Giggles. While it’s not public knowledge how the two met, they’ve been hanging out since 2012. The two have been spotted at various events and awards ceremonies together, often pictured laughing together on their way in or out of the event.

They’ve even popped up in one another’s social media posts, with big, genuine smiles plastered on their faces. McBrayer was even invited to sit with Skarsgard and the rest of the cast of Big Little Lies during this years SAG Awards. While this was initially believed to be part of a campaign by the ceremony to put more dynamic, “fun” actors front and center of the televised event, it has since come to light that he was just sitting there because his best friend wanted him nearby during an awards show. That’s so unbelievably sweet, and also just unbelievable in general.

10 Bette Midler and 50 Cent

VIA: OhNoTheyDidn't

Seriously! Bette Midler is a legend in the world of musicals and a classically trained actress. One of the last people we ever thought we’d seen her with would be the rapper, actor, and entrepreneur, 50 Cent. But not only have the two met, the two actually seemed to get along swimmingly. Midler has an environmental group based in NYC, known as the New York Restoration Project. 50 Cent worked with the organization to help put together a public garden in the neighborhood where he grew up, and was more than happy to work with her.

The two hit it off, setting up a number of future charitable meetings. Midler told E! News about the meeting, saying "Little, Jewish lady and the great, big rapper… He's such a doll. I love him. He's gorgeous. He's one of the newest members of our tribe. He's really made my life worth living." Midler has even floated the idea of the pair of them busting out a duet at an event, but we haven’t seen that yet. But, hopefully, they actually do something like that, because 2018 just hasn’t been weird enough. And guess what? This isn’t even the last time we’ll see 50 Cent on this list.

9 Courteney Cox and Ed Sheeran

via: Fuse

Courteney Cox became a permanent part of the pop culture lexicon with her role as one of the six titular, Friends. The NBC sitcom ran for ten years and eventually became such a success for the network that each actor was being paid a million dollars to appear in any given episode. So it’s no surprise that they’ve all been able to relax somewhat in the years since the show ended. And Cox seems to be loving the way things are going for her and her real life friends, including, surprisingly enough, the award winning British singer, Ed Sheeran.

The actress (who divorced from David Arquette in 2013, although, the two remain on good terms) became fast friends with Sheeran, quickly appearing in one another’s social media feeds. Sheeran even set up Cox with a musician friend of his, Snow Patrol’s, Johnny McDaid. Cox has been with McDaid ever since, and their relationship with Sheeran has only gotten better. It reached the point that when Sheeran came to California to work on music in 2014, Cox offered him a room in her Malibu beach house completely rent free. According to the Daily Mail, Sheeran said it was wonderful, and that he treated the home of his friend with the kind of respect that it deserved.

8 Beyoncé and Gwyneth Paltrow

via: Virgula

Let’s be honest, Beyoncé is probably one of the closest things we have to American royalty. The beloved singer has only been rising in clout in recent years, with her legion of fans turning out and defending her work. She’s been unabashedly political, and refreshingly blunt with her commitment to black women in the United States and the struggles that they go through. But even the stars need time to refresh and just hang with their buddies. It’s just surprising to think of her hanging out with lifestyle guru, Gwyneth Paltrow. But be that as it may, the Goop founder is close friends with the singer according to InStyle, appearing with her at a number of award ceremonies.

Paltrow has said that the friendship has actually benefited her acting, and that she’s been inspired to become a better singer, thanks to Beyoncé. The friendship even extends to their children, with their daughters, Apple (that Gwyneth had with Coldplay frontman, Chris Martin) and Blue Ivy (that Beyoncé had with Jay-Z), even bonding over the years. There have been play dates a plenty, both just between the mothers backstage at concerts and brunches with the kids. Either way, both women seem to love their friendship and what they bring to one another.

7 Ron Howard and Jamie Foxx

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Howard spoke to Entertainment Weekly about the pairing, and described it as one of the most unique experiences of his life. He said, “Jamie came over and said, ‘Hey, I’m shooting a video in L.A., will you come by?’ I was picturing a sort of ‘We Are The World’ thing. So I showed up, and Jamie said, ‘It’s this party scene, and you’re going to drive up with Jake Gyllenhaal and Forest Whitaker and me. The only thing is that you’ve got to wear your party face.’ At least Foxx gave Howard a case of champagne as a thank you.

6 Jennifer Lopez and Leah Remini

via: Zimbio

Leah Remini has become one of the most controversial women in Hollywood, largely due to her attempts to bring the secrets of Scientology into the public light. Her cooperation with documentaries, which make startling accusations about the church, has made her a pariah in certain circles of Los Angeles, and she’s fallen out of contact with friends who are still parts of the culture. But there’s one woman in Hollywood who doesn’t care about the Scientology connection and the rules, she’s going to stay loyal to her buddy, according to the Daily Mail. Jennifer Lopez has remained close to Remini, despite the threat of her father (who is a Scientologist) possibly being turned against his daughter in retaliation for Remini’s commentary. The two have remained as close as ever, even appearing in films together such as Second Act. They were seen on set messing around in between takes. They’ve been friends for over 20 years, and have supported each other through the highs and lows of their respective careers. It’s nice to see them so close even all these years later, especially in light of the criticism that Remini has had to endure since leaving the Church of Scientology. And it doesn’t look like it’ll end anytime soon.

5 Chris Hemsworth and Emily Blunt

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Chris Hemsworth has risen in recent years to global stardom in his role as Thor for the Marvel Cinematic Universe. But he’s also proven to have the perfect personality for the job, easily personable and charming. He just seems like an incredibly nice guy! It’s nice to see that seemingly confirmed by his ease of making friends on the set of his movies. He’s been spotted hanging out with his fellow Avengers since the MCU films started crossing over. But he’s also been seen on some of the coolest double dates ever. He befriended Emily Blunt on the set of The Huntsman, with the pair getting along so well that they even started setting up double dates with their respective romantic partners, according to People. It’s not all that shocking to see Blunt being so friendly though. Her and her husband (former Office star and her co-star in A Quite Place, John Krasinski) have actually proven to be surprisingly good friends with other celebrities such as Jimmy Kimmel and Jennifer Aniston, even vacationing with some of them during vacations and parties. But seeing them enter into that kind of friendship with Chris Hemsworth and his wife, Elsa Pataky, is just all kinds of adorable.

4 Vin Diesel and Judi Dench

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Vin Diesel is one of the biggest stars in the world, largely due to his time at the center of the Fast & the Furious film franchise. He’s also something of a massive nerd. He’s been playing tabletop roleplaying game, Dungeons & Dragons, for years. He’s also been incredibly open about this pastime, sharing the fun with many of his cast mates over the years (including other major action stars/secret geeks like Dwayne Johnson). But one of the most surprising players he’s been able to recruit for his games has got to be Dame Judi Dench, a mainstay of British cinema and theater. According to Hollywood.com, the two met on the set of The Chronicles of Riddick and got along quickly, and Diesel eventually introduced her to the game. Dench apparently took a real liking to the game, and played with Diesel for the rest of their time on set for the movie. Judi has taken the pastime with her beyond her time with the action star, reportedly even playing the game with her grandchildren and as the Dungeon Master, no less. Sometimes, it’s our most surprising friendships that teach us some of the most surprising things we love the most.

3 Eminem and Elton John

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Earlier in his career, the rapper, Eminem, found himself under fire for some of the comments he made regarding gay people. He used slurs in his music that casually belittled the gay culture, and often turned it into a joke. In an attempt to fight back against these accusations, Eminem asked Elton John to join him on-stage for a performance in 2001. John joined him and helped Eminem regain some of his good standing with everyone, it also introduced the world to an unlikely friendship, as detailed by Refinery29. Both men respect one another on a professional level, with John especially recounting just how impressed he was with Eminem’s album, Marshall Mathers.

The two stayed in contact and supported one another ever since, with John becoming a stabilizing force in the rapper’s life. John was a major source of reliance when Eminem was trying to get his life on track, having been through rehab himself in the 1990s.

They’ve called one another dear friends for years not, and have praised one another and their work over the years. They’ve even released a phone interview between themselves where they reaffirm their friendship and feelings about one another. They might not see each other every day, but their loyalty to one another is inspiring.

2 Russell Brand and Helen Mirren

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Since then, Brand has been very open about how much he cares for the older actress, describing them as an unconsummated relationship.

Both have gone out of their ways to talk up the other. During an interview with the Telegraph, Brand said, “It's complicated. It's an unconsummated love affair. An erotic, intellectual tangle of emotions between a Dame and a vagabond. She is an incredible personality, very beautiful; ordinary when she needs to be, remarkable when required. I really love her and I respect her tremendously."

1 Meryl Streep and 50 Cent

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50 Cent has proven to be a surprisingly easy fellow to befriend famed female entertainers. There is, of course, his previously mentioned bond with Bette Midler. But he’s also turned out to be a surprisingly good friend to one of the most successful actresses of all time, Meryl Streep, according to the Daily Mail. The rapper invited the actress and her husband to join him courtside during a game between the Los Angeles Lakers and the New York Knicks. The two were giggly during the course of the game, even holding hands and sharing jokes during the game. The two ended up posting plenty of selfies from the event, and even attended a huge after-party thrown by Kobe Bryant together.

The two are some of the most unexpected pairings of celebrities that we could imagine, but how happy they seem to make one another just proves how people from entirely different avenues of life and upbringing and even presentation can find common ground and become the most unlikely of companions.

A gangsta rapper can end up hanging out with an Academy Award record setting star and make it feel natural and easy, and that’s nice to know even if it’s still a bit surprising.

References: Rolling Stone, People, PopSugar, People, Marie Claire, InStyle, Vulture, Hollywood Life, Mirror, Mirror, Marie Claire, PopSugar, HelloGiggles, E! News, Daily Mail, InStyle, Entertainment Weekly, Daily Mail, Hollywood.com, Refinery29, Telegraph, Daily MailHuffington Post

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