When you’re a celebrity, you’re used to rubbing elbows with a variety of people, some who may or may not be within what you’d consider your circle of regular friends and hangers-on. You meet on the red carpet, at press junkets, conventions, award shows, film festivals, on set, anywhere! In the life of a celebrity, they’re traveling so often and meeting so many new people that it shouldn’t be that shocking to see them hanging out with people we would never dream of them being in the same room with.
Despite all that, however, there are some unlikely celebrity duos who have transcended the bonds of a casual meet-up and become friends, even though it seems unlikely and downright weird to catch them hanging out together! Even the photographic proof requires a double-take. Sometimes, we get used to it and even embrace it, like the random pairing of Martha Stewart with Snoop Dogg, while others still have us wondering how on Earth they met in the first place! From BFFs to casual dinner acquaintances, these 15 photos will have you wondering just WTF those celebrities found to talk about and how they managed to form such a tight bond!
15 Selena Gomez & Jennifer Aniston
These two both seem like absolute sweethearts, so perhaps we shouldn’t be so shocked that they’ve been secret BFFs for years now! Despite their age difference, Selena Gomez and Jennifer Aniston have regularly popped up in cute snapshots together and have even spent evenings making pizza together in Aniston’s pizza oven! The pair met the way many Hollywood friends do–through their management–and Gomez has since credited Aniston with being on-hand to provide helpful maternal advice. Owing to the fact that both of these ladies have seen their fair share of highly publicized heartbreak, we imagine that there’s a lot of wisdom to be passed on!
The feeling of friendship is mutual between this unlikely celebrity pairing, with Gomez gushing that Aniston is “very cool and very sweet,” and Aniston saying of Gomez, “She’s just like a little cherub that I feel like I wanna take care of…she’s been extremely supportive and wonderful.” Aww!
14 Lena Dunham & Taylor Swift
Taylor Swift is as known for her ultra-famous glam girl squad as she is for her endless list of exes. But, perhaps one of the oddest additions has been Lena Dunham, the creator and star of the HBO show Girls. Throughout much of her career, Swift has positioned herself as a country, feminine, cutesy type whereas Dunham is distinctly more rough around the edges. Additionally, it might be worth noting that the regular attendees in Swift’s carefully-cultivated squad are those who list “Victoria’s Secret Angel” on their resumé–something that Dunham certainly is not.
Beyond the superficial discrepancies in this celebrity duo which, in all honesty, rank pretty low for us, we think the oddest thing may be the fact that Dunham is an outspoken feminist while Swift is…well...a little less. To be fair, Swift did credit Dunham for opening her eyes to the issues of gender equality, but we can’t help but feel that perhaps Swift simply added Dunham to her ever-growing list of friends in order to latch on to the hottest up-and-comers in another step towards polishing her pristine image.
13 Clay Aiken & Tyra Banks
When it comes to celebrity friendships, you can’t get more ‘00s than this random duo! Way back 2006, American Idol runner-up Clay Aiken met supermodel Tyra Banks back when she was hosting her talk show, Tyra. Since that meeting over a decade ago, the two have managed to keep in touch (although to be fair, neither seem to be doing a whole lot right now).
In a 2009 interview with People magazine, Aiken discussed his upcoming appearance on another Banks show, America’s Next Top Model, and reminisced about how their friendship first blossomed, saying the two immediately clicked upon meeting. “She’s such a real person,” Aiken said. “She doesn’t try to be something she’s not…I think that’s why people are attracted to her, and I think that’s why we became friends.” We haven’t heard all that much from Banks on the subject of her friendship with the musician-turned-politician, so this celebrity coupling might be a bit one-sided, but there’s no way to know for sure!
12 Kelly Osbourne & Kim Kardashian
Back when Kelly Osbourne first burst onto the scene, she was a sneering teen with dyed hair and a filthy mouth who didn’t shy away from getting into feuds with the biggest divas of pop music, ridiculing them for their superficiality.
With that being said, it’s pretty funny to know that Osbourne now buddies up to none other than socialite and entrepreneur Kim Kardashian! However, these two have a lot more in common than meets the eye, like the fact that both women were subjected to the intense scrutiny of themselves and their family that comes from having the most intimate parts of their lives broadcast for reality TV entertainment! Osbourne and Kardashian are such good friends that the former was even invited to the latter’s baby shower for daughter North and publicly stuck up for her friend when media outlets began body-shaming the pregnant reality star, calling it “deplorable” that anyone would fat-shame a pregnant woman. Despite their differences, this seems like a solid friendship and the type of duo that will always have each other’s backs!
11 Martha Stewart & Snoop Dogg
Once upon a time, this celebrity pairing would have raised more than a few eyebrows, and while it does still seem a bit weird to see them both together, Martha Stewart and Snoop Dogg have defied the odds and seem like the best pair of pals anyone could hope to be a part of!
The two met during the Comedy Central Roast of Justin Bieber (where Stewart killed, naturally), and the domestic goddess and rapper struck up such a solid friendship that they even have a cooking show together now (called Martha & Snoop’s Potluck Dinner Party, in case you’re interested)! Before getting their own show together, Snoop would make fairly frequent guest appearances on Stewart’s own show, and their chemistry and camaraderie were off-the-charts. So, of course, studio execs decided that we viewers needed to see them together more often! However strange and absurd this celebrity duo may seem, Snoop and his “homegirl” Martha are definitely one of our favorite celebrity friendships.
10 Blake Lively & Florence Welch
Blake Lively is often considered to be the all-American type, with her sunny smile and blond goddess hair, but we know she must have a quirky, funny side because she gets along with the King of Sarcasm, Ryan Reynolds, so well! Because of that, we think it kind of makes sense to see that she’s besties with Florence Welch of Florence + the Machine because she’s got to have a bit of weirdness underneath that Cali tan (even if it’s odd to see these two together).
In addition to being such good friends, Welch has a major fan in Lively too. She came to her band’s very first show! Since then, Lively has helped her BFF out in the career department just a bit, getting her a gig on her TV show Gossip Girl and even having Welch sing at Lively’s super-secret wedding to Reynolds. Clearly, great taste in music and a fearlessness when it comes to fashion are only some of the ties that bond these two lovely ladies.
9 Kanye West & Kristen Stewart
Since both Kanye West and Kristen Stewart are known for their resting b*tch face, perhaps we shouldn’t be quite so surprised that they found each other; only that they were able to relax enough to let one another know that they hadn’t pissed the other off!
We don’t know how close these two actually are, because all we have to show off their friendship is this photo taken in Paris back in 2015. However, that doesn’t mean that both Stewart and West haven’t maintained some sort of bond, since they’re known for being low-key when it comes to their friendships (which is about the only low-key thing West is known for). That being said, even if this was a one-time thing, it still looks pretty odd, wouldn’t you say? We don’t know under what circumstances this celebrity duo would cross paths, and we so wish that we could have been a fly on the wall in that room just to hear that conversation! Although, judging by their expressions, perhaps not much was said at all.
8 John Mayer & Bob Saget
Don’t let that face fool you. We bet they had a great time! We may be used to him as the Windex-happy dad in Full House, but Bob Saget is not Danny Tanner. Actually, he’s a whole lot raunchier, and some of his stand-up might just destroy your childhood. Because of that little fun fact, it slightly tempers the weird factor of Saget hanging out with notorious womanizer and musical bad boy John Mayer, but only slightly.
This photo was taken outside a restaurant where this unlikely bromance went for dinner, but the two have actually been pretty good buddies for years! In addition to sending some social media love, these two like to goof around together, like back in 2008 when a video surfaced of Mayer acting as “crowd control” for Saget! Mayer also performed at one of Saget’s charity functions back in 2015, and in a 2016 interview, Saget called Mayer one of his dearest friends. So hey, sometimes weirdness works!
7 Rihanna & Jim Parsons
He plays a super-awkward, socially-obnoxious nerd and physicist on The Big Bang Theory while she’s the epitome of the laid-back cool girl. But Jim Parsons and Rihanna are actually pretty close, as strange as it may seem! You may not recall, but the two actually paired up to lend their voices to the animated film Home (which cast Parsons as an alien, keeping him firmly in his comfort zone). Since then, friendship has bloomed between these two random celebs.
Parsons, proving that he’s just like the rest of us, said in an interview with Ellen DeGeneres that while working on the film, he developed a “weird crush” on his gorgeous co-star despite being gay and in a committed relationship. The two seemed to bond over their mutual goofiness, but we know that both have pretty packed schedules, so it’ll be interesting to see if this random BFF pairing was able to continue since the press tour for Home has long since ended.
6 Vince Vaughn & Robert Pattinson
There are celebrities you can picture getting together for a few beers after a long day on set, and then there’s Vince Vaughn and Robert Pattinson who, as strange as it may seem, have become drinking buddies in one of the strangest friendships to be seen in Hollywood.
Way back 2013, when Pattinson was still with Twilight co-star Kristen Stewart, he got together for a guys’ night with Vaughan and Joaquin Phoenix, making this random duo an even more random trio! Considering the fact that Pattinson has tried to keep a low profile after exploding onto the celebrity scene and into the hearts of tween girls back in 2008, it’s odd to see the camera-shy star buddying up with a major A-lister like Vaughan (Owen Wilson was also in attendance that evening). We can’t say if these two kept things going, but it’s possible, especially since nothing as time-sensitive as a film brought them together in the first place.
5 Mindy Kaling & Reese Witherspoon
Now, if you’ve seen the recent trailer release for the upcoming movie A Wrinkle in Time, based on the novel by Madeleine L’Engle, perhaps this friendship doesn’t seem all that random to us, and while it’s the stuff of our #squad dreams, we still have to admit that this duo took us a little by surprise!
Mindy Kaling is absolutely hilarious as a writer, actor, and comedian with her own show and a couple books under her belt. Reese Witherspoon is similarly ambitious as she’s an Oscar-winning actor with her own line of clothing and housewares called Draper James. While these two have only recently bonded (with Oprah, no less, to add to your envy), there was a little bit of mutual fandom that seemed to happen first. In an episode of Kaling’s TV show, The Mindy Project, Kaling’s character proudly displayed her “Wreath Witherspoon” which was–you guessed it–a holiday wreath featuring images of the actress! In return, Witherspoon offered a dress patterned with Wreath Witherspoons on her own website!
4 Kris Jenner & Jennifer Lawrence
Kris Jenner knows what it takes to be a celebrity, which means that she’s likely to rub elbows with most of the famous Hollywood set, especially if it helps her stay relevant. While Jennifer Lawrence doesn’t exactly seem like the type to buy into this level of superficiality, she has admitted to being a die-hard Keeping Up With the Kardashians fan in the past, so while this crazy strange celebrity duo might make a bit of sense, it still strikes us as awfully weird!
Both ladies, despite the age difference, seem like they’d be a hilarious addition to any party. And while Jenner was the one who posted this snapshot wishing the Oscar winner a happy birthday, the award-winning Lawrence was in awe of the most famous momager ever, saying that when she met her, her “...knees buckled. It was the closest I’ve ever come to losing consciousness!” Subtlety isn’t in the vocabulary of either of these ladies, so maybe this duo makes more sense than what meets the eye!
3 Ed Sheeran & Courteney Cox
By now, we’ve all probably heard about how Ed Sheeran was couch surfing in the homes of the rich and the famous (including Jamie Foxx) before he made it big. But his odd friendship with Courteney Cox goes beyond that. This unlikely celebrity duo met back in 2013, when Sheeran introduced Cox to her current fiancé, Snow Patrol frontman Johnny McDaid. Around that same time, Cox allowed Sheeran to shack up in her beach house for several months while he worked on music for his upcoming album! (Sheeran, for his part, admits that while he introduced Cox and McDaid, it was actually Sacha Baron Cohen who set them up, adding to the randomness of this pair!)
Sheeran seems to have been able to buddy up to almost everyone in Hollywood, but it sounds like he has a special place in his heart for Cox and her other real-life BFF and former co-star, Jennifer Aniston, saying on a few occasions that both ladies are actually really normal and incredibly friendly!
2 50 Cent & Bette Midler
“Little Jewish lady and the great big rapper” may sound like a pitch for a weird sitcom, but it’s how Bette Midler describes her unlikely friendship with 50 Cent, and it couldn’t be more to the point! These two first met back in 2008 when 50 joined Midler’s New York Restoration Project, which the Broadway star founded in 1995. Even though 50 later complained of money woes on Twitter, at the time, Midler said he didn’t care about cost and simply wanted to know where he could sign up to join.
For her part, Midler returned the favor and joined 50 at the opening of The Curtis ‘50 Cent’ Jackson Community Garden, which was named for the rapper but was part of Midler’s Restoration Project. The fact that these two bonded over their charitable endeavors and big hearts is beyond adorable, and while we haven’t seen many recent snaps of this unlikely pair, we hope that this truly odd friendship couple can keep things going!
1 Meryl Streep & 50 Cent
It seems like 50 Cent has a thing for older, multi-talented women because how else do we explain his bizarre friendship with Meryl Streep? (For the record, he has also publicly admitted to his adoration of Helen Mirren, so we’re sensing a pattern here.)
Back in 2014, 50 and Streep were spotted at a Knicks/Lakers game, and they seemed to hit it off because who wouldn’t want to be BFFs with Meryl Streep? In addition to the shots taken by photographers at the game that showed the two giggling and holding hands, 50 posted his own images to Instagram, with captions like “Things got a little gangsta” and “Man I got a good life man.” In a shot showing Streep, 50, and Kobe Bryant, 50 fangirled and captioned it, “Best ball KOBE, Best Rap 50, Best Actress Meryl Streep. TOP THAT”
This pairing is clearly the most random we’ve ever seen, but it definitely one of the cutest in recent years. And we hope that these two managed to get together for another ball game!