16 Celebrity Friendships You’d Never Expect

Hollywood is overflowing with familiar faces—red carpet icons, tabloid regulars, and award-show darlings. But every now and then, a celebrity friendship pops up that makes you pause mid-scroll and think, Wait… they’re friends? And not just friendly in a posed-for-a-photo kind of way, but real-life, grab-lunch, text-each-other-on-the-regular kind of friends.

Sometimes it’s the shared trauma of fame. Other times, it’s just a strange twist of fate or the purest form of “weird vibes that match.” Whether it’s a former president hanging with a pop star or an Oscar-winning actor bonding with a reality TV icon, these duos remind us that friendship doesn’t obey the rules of logic—or genre.

So, if you’ve ever wondered who your favorite A-lister is secretly brunching with on Sundays, this list might surprise you. Here are 16 of the most unexpected, head-scratching, and oddly heartwarming celebrity friendships out there.

1. Jennifer Aniston and Selena Gomez

Jen calls Selena a “little cherub” she wants to protect, and honestly, that sounds like the plot of a buddy comedy we’d watch in a heartbeat. They’re proof that Gen X and Gen Z can get along—especially when there are dogs and skincare involved.

2. Blake Lively and Florence Welch

They’ve been close friends for over a decade, and Blake even had Florence perform at her wedding. Florence’s ethereal voice paired with Blake’s Upper East Side glam? It’s giving fairytale meets fashion week.

3. Helen Mirren and Vin Diesel

Queen of British stage and screen Helen Mirren and gravel-voiced action star Vin Diesel sound like they belong in separate galaxies—but Mirren gushed, “I adored Vin from the moment I met him.” They’ve even worked together in the Fast & Furious franchise, which somehow makes this even better.

4. Snoop Dogg and Martha Stewart

The friendship that launched a thousand memes. The rapper and the domestic goddess met in 2008 and have been cooking, laughing, and roasting each other ever since. Their dynamic? Imagine your weed-loving uncle hanging out with your mom’s poshest friend—and they’re the life of the party.

5. Elton John and Eminem

After performing together at the 2001 Grammys, this unlikely friendship blossomed. Elton even became Eminem’s sobriety sponsor. From flamboyant piano ballads to Detroit rap battles, they couldn’t be more different—and yet, somehow, perfect for each other.

6. Macaulay Culkin and Lizzo

Yes, Kevin McCallister is besties with the “Good as Hell” queen. Macaulay tweeted about seeing her live and called her his friend. Their energy is so opposite it loops back around to complementary. She’s loud and proud; he’s chill and weird. It works.

7. Kris Jenner and Jennifer Lawrence

Kris called Jen her “favorite daughter” on her 30th birthday, and they’ve had multiple sleepovers. Picture it: the reigning queen of reality TV and the Oscar-winning goofball eating snacks in silk pajamas and gossiping about boys. Chaos, but in a cashmere robe.

8. Diane Keaton and Justin Bieber

They met while filming the “Ghost” music video and just… clicked? The hat-loving Hollywood icon and the tattooed Canadian pop star don’t seem like a natural match, but their banter online suggests genuine affection. Somewhere between Annie Hall and Yummy, love bloomed.

9. Pitbull and John Travolta

Mr. Worldwide and Danny Zuko? You read that right. Travolta once gave a heartfelt speech at Pitbull’s handprint ceremony and described their friendship as “forever.” Apparently, what unites them is not just style, but soul. Who knew they were a brotherhood of bald?

10. Michelle Obama and George W. Bush

Their bond blossomed… at funerals. According to Bush, the two always end up sitting next to each other at official events. “I start cracking a few jokes, and she seems to think they’re funny,” he said. A former president and a former First Lady bonding over funeral humor? Oddly wholesome.

11. 50 Cent and Bette Midler

This might be the most random pair on the list. The rapper and the Broadway legend met while working on a community restoration project, and Bette even said, “He’s really made my life worth living.” Just imagine The Divine Miss M at a G-Unit show.

12. Andy Cohen and John Mayer

These two are so close, people constantly assume they’re a couple. Cohen says they’re in a “deep friendship,” and Mayer calls it “love.” They’re like a modern-day Oscar and Felix—if both had podcasts and a penchant for tequila.

13. Jamie Foxx and Ed Sheeran

Foxx let Sheeran crash on his couch for six weeks before he was famous. He even had Ed perform at his club’s open mic night. Imagine Jamie Foxx being your temporary landlord, agent, and hype man—no wonder Ed made it big.

14. Drake and Adele

When Adele dropped “Easy on Me,” Drake called her “one of [his] best friends in the world.” Imagine those text exchanges. One’s pouring his heart out about heartbreak, and the other’s like, “Same.” They’re sad song soulmates.

15. Cardi B and Penn Badgley

This friendship kicked off online when Penn Badgley praised Cardi B’s raw authenticity—and Cardi, thrilled, fangirled right back. What started as mutual admiration on Twitter quickly blossomed into a real-life connection that no one saw coming. The introspective Gossip Girl star and the Bronx-born rap queen might seem like an odd duo, but somehow, it just works. XOXO, WAP.

16. Zach Braff and Harry Styles

Their friendship first sparked while Zach Braff was dating Florence Pugh, but even after the romance ended, the bond between Braff and this unexpected bestie only grew stronger. Zach affectionately calls it a “bromance,” and from the looks of their beach hangs and goofy Instagram banter, it’s the kind of friendship that feels effortless and real. Honestly, we’d give anything to third-wheel one of their laid-back beach days—sunscreen, sarcasm, and all.