Surprising Celebrity Friendships
I guess when you’re out and about in Hollywood, you meet a lot of different people—and bond over different things. These unexpected celebrity friendships might not always make sense, but they make it work.
Betty White And Jennifer Love Hewitt
I’d say this is a friendship that transcends generations, but frankly, I can’t imagine anyone not getting along with Betty White. This pair of pals met on the set of a Hallmark movie called The Lost Valentine in 2011 and have been friends since. Hewitt shared that they both have an affinity for gummy bears.
Britney Spears And Mel Gibson
When it comes to stars that have really been through it in their time as celebrities, few come close to Britney Spears and Mel Gibson, each of whom have had their very own disturbing—but also very different—personal struggles. When Spears was going through a bad period in 2007, Gibson felt terrible and reached out to her to offer his support.
He ended up taking her on a getaway to Costa Rice a year later, in order to get her away from her troubles—and the paps.
Diane Keaton And Justin Bieber
No one has weathered the ups and downs of fame over the course of decades like Diane Keaton—so it makes sense that she would get along with Justin Bieber, who’s had so much scandal and drama packed into the decade or so that he’s been famous. Bieber cast Keaton in the tearjerker video for his song “Ghost,” and they’ve stayed friends ever since.
David Beckham And Snoop Dogg
Everyone knows about Martha Stewart and Snoop Dogg’s friendship, but it turns out that Snoop gets around in Hollywood. When Beckham and his family first moved to LA, Snoop was one of the first people he met, and he even appeared on the rapper’s reality show.
Courteney Cox And Ed Sheeran
We have James Corden to thank for this friendship.
All it took was once appearance on his show together, and Courteney Cox and Ed Sheeran have been friends ever since. She must have a lovely home, because Sheeran opts to stay there whenever he visits LA, and they’ve documented their jam sessions on her Instagram.
50 Cent And Bette Middler
Speaking of Snoop, this one feels like they saw the friendship between Snoop Dogg and Martha Stewart and decided to create their own version.
Well, actually, it was 50 Cent’s prolific success at charity work that drew the attention of Middler. She saw that he was able to raise millions through his G-Unity Foundation and she called for advice—and the rest is history.
Lea Michele And Kate Hudson
Lea Michele from Glee often gets a bad rap due to her behavior on-set—but when she unexpectedly lost her co-star and boyfriend Cory Monteith in 2013, Kate Hudson stepped forward to help. At a time when the paparazzi were desperate for a photo of Michele and were stalking her family, Hudson left them stay at her house—and even stocked the fridge with Michele’s favorite juice.
Matthew McConaughey And Guy Fieri
McConaughey came across Guy Fieri the way many of us do—traveling and have nothing to watch on TV except Diners, Drive-Ins, and Dives. But unlike most of us, after watching many episodes, McConaughey reached out, presumably through a series of agents, to get Fieri’s number and heap praise on the chef/TV host. The two have been friends since and McConaughey spoke at Fieri’s Hollywood Walk of Fame induction ceremony.
Albert L. Ortega, Getty Images
Helen Mirren And Vin Diesel
This one may seen like a bit of a “How did they meet” situation, until you remember that Mirren has appeared in the Fast and the Furious franchise, playing the mother of Jason Statham’s character. Though those sets can be infamously icy—Diesel and Dwayne “The Rock” Johnson have had their share of issues—Mirren said that she had immediate chemistry with Diesel, which led to a solid friendship.
Jennifer Lopez And Leah Remini
One is from the Bronx, and one is from Brooklyn.
Both took very different trajectories in Hollywood but have maintained a friendship over the course of many years—thought recently, it was reported that Lopez’s marriage to Ben Affleck was causing a rift in their relationship.
BG002/Bauer-Griffin, Getty Images
Gwyneth Paltrow And Jay-Z
Though Gwyneth Paltrow may come off as standoffish or a bit granola due to her lifestyle website, Goop, she definitely has one thing in common with her old pal Jay-Z and his wife Beyonce: they’re all mega-rich. And it turns out that Paltrow is also a huge hip-hop fan.
Jay is also friends with Paltrow’s ex, Chris Martin, who he called a genius.
Patrick McMullan, Getty Images
Melissa McCarthy And Octavia Spencer
Both McCarthy and Spencer toiled away in supporting roles in TV and film before breaking out and finally getting the attention they deserve as leading ladies. And they’ve been friends the whole time! In 2021, they appeared in the movie Thunder Force, together, which McCarthy said was a dream come true—since she got to spend three months straight together with her bestie.
Zach Braff And Harry Styles
Despite pushing 50, Zach Braff doesn’t discriminate when it comes to age—remember when he dated Florence Pugh? And that doesn’t just apply to romances, either. Braff made friends with Harry Styles years ago through mutual friends and they’ve had what Braff calls a “bromance” ever since.
John Travolta And Pitbull
Who wouldn’t want to be friends with Mr Worldwide? It seems like a good time, after all.
But one thing that John Travolta has a one-up on? He calls Pitbull by his government name, Armando. Travolta said that when the two first met, he told Pitbull he wanted to be friends forever.
Cardi B And Penn Badgley
Turns out that more people than you’d expect are secret Gossip Girl fans—Cardi B included. After Cardi B and Penn Badgley, who played Dan on the show, had a Twitter exchange, she changed her avatar to a picture of his face.
METROPOLIS/Bauer-Griffin, Getty Images
Kim Kardashian And Serena Williams
They’re both incredibly famous and filthy rich, but those aren’t the things that brought Kim Kardashian and Serena Williams together. Many, many years ago, before the reality show and even the Ray J tape, Kardashian had a job organizing closets for celebrities. She worked with tennis star Williams, and they’ve been pals ever since.
Dimitrios Kambouris, Getty Images
Kelly Osborne And Mandy Moore
The pop girlie wars of the early 2000s were fierce—and Kelly Osborne positioned herself as the antidote to sugary sweet pop like the kind made by “Candy” singer Mandy Moore. Regardless, when Elle Girl brought the two together in 2003 for a cover shoot, they became friends, and have stayed close ever since.
Tyra Banks And Clay Aiken
Where would TV in the early 2000s be without Tyra Banks and Clay Aiken?
Despite coming in second on American Idol, Aiken stuck around in Hollywood, and appeared on Banks’ talk show in 2006. He also got to flip the script and appear on an episode of America’s Next Top Model opposite the crew of contestants in 2009.
Patrick McMullan, Getty images
Jennifer Lawrence And Kris Jenner
Everyone knows that Jennifer Lawrence has a reality TV obsession—so it makes sense that she befriended reality’s #1 matriarch, Kris Jenner. Jenner ever once called Lawrence her “favorite daughter” on her birthday.
Stefanie Keenan/VF24, Getty Images
Elliott Page And Ruby Rose
Hollywood, and all the attention that comes with it, can be a scary place for LGBT people, who often face harassment and bullying.
It can help to have a friend who understands that unique experience. In 2016, Ruby Rose wrote a heartwarming message to Elliott Page on his birthday, expressing her gratitude for his fearlessness and loyalty.
Rihanna And Natalie Portman
When it comes to their respective fields, both are at the top of their games.
Though they may seem very different, the pair recently made friends at a Dior fashion show, where Rihanna heaped praise of Portman and said she was the “hottest […] in Hollywood”.
Alison Williams And Katy Perry
Perry’s music is certainly different from anything that Alison William’s character Marnie and her partner Desi came up with on the show Girls—but Williams showed her true-blue friendship to Perry on the red carpet in 2013. That’s when she came along to the Grammys as Perry’s date shortly after the singer’s break-up from John Mayer.
Christopher Polk, Getty Images
Blake Lively And Florence Welch
Sometimes you don’t realize just how small Hollywood can be until you discover an unlikely friendship through Instagram. In 2018, Blake Lively posted a photo to mark ten years of friendship with singer Florence Welch.
Crazy how times flies!
Jennifer Aniston And Selena Gomez
Child stars go through so much in Hollywood, and they grow up so fast. Perhaps that’s why Selena Gomez is yet another star who has no problem making friends across generations. Aside from her collab with Steve Martin and Martin Short, there’s also her longtime friendship with Friends star Jennifer Aniston. They met through their manager, and Aniston has taken on a protective role over the multi-hyphenate Gomez.
Kevin Mazur/VF15, Getty Images
Drake And Millie Bobby Brown
People tend to forget that Drake, AKA Aubrey Graham, was once a teen star on an intensely popular TV show, playing Jimmy Brooks on Degrassi: Next Generation. Perhaps, because of that experience, he’s had tips to give to Millie Bobby Brown, star of Stranger Things. Though their friendship has come under fire, Brown has defended Graham, and said he’s offered wisdom and guidance.
Snoop Dogg And Martha Stewart
It’s less of a surprise now—after all, they’ve appeared in multiple shows and commercials together over the past decade or so. But when it first happened, the friendship between Snoop and Martha Stewart was a big surprise.
Since then, Snoop has had Stewart singing the praises of entourages. She’s said, "That's why all the comedians have sidekicks and bands because it loosens them up and lets them be freer. Snoop is my freedom". It really seems like they truly complement each other.
Drake And Adele
Drake is a famously sensitive guy—and no one sings ballads like Adele. These two soft-hearted sweeties have expressed their support for each other’s career on Instagram, where Drake once called Adele “one of his best friends in the world”.
Kristopher Harris, CC BY 2.0, Wikimedia Commons
Connie Britton And Senator Kirsten Gillibrand
Though it’s not uncommon for actors and musicians to cross paths, it’s less common for Hollywood types to hobknob with politicians outside of fundraisers and correspondent dinners. However, it’s not just fame that brought these two together. They were actually roommates in college.
Taylor Swift And Zoe Kravitz
Swift has plenty of A-list friends—remember her Fourth of July photos with Blake Lively and Ryan Reynolds? But she’s also tight with Big Little Lies’ Zoe Kravitz…so close in face, that the two were in the same pod during Covid-19 lockdowns.
Andy Cohen And John Mayer
One is the King of Bravo TV and wrangler of multiple reality casts.
The other plays with the reformed Dead & Co. Though it’s unclear if a mutual fandom of the Grateful is what brought them together, one thing is for sure: the two are so tight that rumors often fly that there might be a romance there.
Michelle Obama And George W Bush
Circumstance brought these two together across party lines.
Due to their previous positions in the White House, each has to attend a fair number of funerals, and end up seated together. To curb boredom, Bush will often tell jokes to Obama, who, he says, laughs at them.
David Hume Kennerly, Getty Images
Elton John And Eminem
Early in Eminem’s career, he caught flak for his prejudiced lyrics about gay people. While many wrote him off, Sir Elton John took an alternate route, instead preferring to show him how wrong he was with a gentle hand.
The two performed together around that time, and have been friends ever since.
Skip Bayless And Lil Wayne
The famous sports commentator struck up an unlikely friendship with the rapper at some point, because in 2023, Bayless posted that he’d spent a “sun-blessed LA afternoon” at Wayne’s, talking about music, sports, and life.
Elton John And Charlie Puth
There’s having a great mentor, and then there’s having no less a figure than Sir Elton John help you with your work. That’s just what John has done for Puth, who admitted that the elder singer lambasted him for his 2019 work.
Macauley Culkin And Natalie Portman
Their careers couldn’t have taken two more different trajectories—but lest we forget, they were both once innocent child stars in the ever-turbulent 90s. They probably have a lot of shared experiences, and Culkin was a guest at Portman’s 2012 wedding to Benjamin Millepied.
Tommy Lee Jones And Al Gore
Jones is a tough nut to crack.
He once famously told his Batman Forever co-star Jim Carry that he “cannot sanction his [Carrey’s] buffoonery”. However, that doesn’t mean he doesn’t have friends out there. Jones and Al Gore have been friends for decades, having been freshman-year roommates at Harvard.
Taylor Swift And Lena Dunham
While Taylor Swift has one of the most carefully-controlled images in the industry, Girls creator Lena Dunham famously speaks her mind—and occasionally sticks her foot in her mouth. Regardless, the two have kept up a friendship for years.
Christopher Polk, Getty Images
Kristen Stewart And Dakota Fanning
Kristen Stewart often gives off an aura that she takes things very seriously, while Dakota Fanning seems more lighthearted. Regardless, both have to weather the difficult journey of being a highly sought-after teen star. Though they have that in common, they’re not those friends who only talk about work, according to Fanning.
Michelle Dockery And Pippa Middleton
To an American, there are two pillars of British culture:
the royal family and Downton Abbey. While the two cemented their friendship as guests at Wimbledon, they actually met years earlier when Middleton made a visit to the set of Downton Abbey, where Michelle Dockery played Lady Mary.
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