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In This Digital Issue

6 Celebrity Friends Who’ve Been Besties for Decades

From Tina Fey and Amy Poehler to Snoop Dogg and Martha Stewart, here’s how famous friends stay tight


a photo illustration shows Oprah Winfrey and Gayle King; Ben Affleck and Matt Damon; Snoop Dog and Martha Stewart; Martin Short and Steve Martin; Randall Park and Ken Jeong; Tina Fey and Amy Poehler
(Left to right) Oprah Winfrey and Gayle King; Ben Affleck and Matt Damon; Snoop Dog and Martha Stewart; Martin Short and Steve Martin; Randall Park and Ken Jeong; Amy Poehler and Tina Fey.
Illustration by Sean McCabe

Hollywood isn’t the easiest place to nurture friendships, with its cutthroat competition and constant media coverage. But away from the red carpets and beyond the glitz, friendships can blossom and grow. These six celebrity friendships have endured decades of shifting careers and public scrutiny. Their bonds reveal lessons we all can learn about loyalty, trust and lasting friendship. 

Gayle King & Oprah Winfrey

Tell the truth, even when they don’t want to hear it

Oprah Winfrey and Gayle King are shown in a photo illustration
Oprah Winfrey and Gayle King first met in 1976 when they worked together at a Baltimore TV station.
Kevin Mazur/Getty Images for Tony Awards Productions

A thoughtful friend lets you vent. A true bestie says, “You’ve told this story three times! What are we doing about it?” That directness is why Oprah Winfrey, 71, and Gayle King, 70, have been friends for nearly 50 years. Take the time King reconnected with a high school flame. Winfrey’s reaction was swift: “Don’t let him into your house.” When King asked why, Winfrey replied, “That was 20 years ago! You don’t know this guy!” King didn’t listen. The man stole a photo and tried to sell it. As King later admitted, “When you have a best friend who tells you the truth, take their advice.”

Brutal honesty wrapped in love has been their glue since they met, in 1976, at WJZ-TV in Baltimore. “Gayle was the only one who said, ‘I think you can do it!’ ” Winfrey recalled of an early career crossroads. King’s refusal to flatter — “Sometimes I’ll just go, ‘That’s just not true. Your hair does not look good’ ” — goes both ways. Spotting King’s colorful statement necklace on CBS Mornings one day, Winfrey texted: “It’s hard to focus with the circus around your neck!”

Earlier this year, when King, who is afraid of turbulence on planes, was offered a Blue Origin space trip, Winfrey pushed her to accept. “Life is about continuing to grow into the fullest expression of yourself,” she told King, who agreed: “Oprah knew what it took for me to do that.” From Texas, Winfrey watched her friend rocket skyward, tears streaming. “I felt deeply that she would regret [not going],” Winfrey said. “And I didn’t want to hear ‘I wish I had gone’ for the next 15 years.”

Ben Affleck & Matt Damon

Loyalties forged in childhood can be fierce — but always need tending

Matt Damon & Ben Affleck are shown in a photo illustration
Matt Damon and Ben Affleck are childhood friends who grew up together in Massachusetts.
Suzanne Cordeiro/Shutterstock

Matt Damon and Ben Affleck met as kids in Cambridge, Massachusetts — two die-hard Red Sox fans who would go on to share apartments, a checking account and, eventually, an Academy Award. Damon was 10; Affleck was 8 and fearless, as Damon later learned. “I once mouthed off to this kid,” Damon told Conan O’Brien. “He was, like, 6 foot 6, and I might have been 5-3.… Ben tackled this dude off of me … literally at the risk of his own life. I thought, This is a good friend to have.”

When they landed School Ties in 1992, they pooled their earnings and “blew it all in a couple of months,” Affleck said. Later, they cowrote Good Will Hunting on a borrowed laptop and cried on the first day of filming, when their long-shot dream became real. But after that Oscar-winning breakthrough, they followed industry advice to “individuate your careers.” Damon, 55, became the blockbuster hero; Affleck, 53, a bit more of the prestige-film guy. They stayed close but mostly avoided working together — until reality shifted the math.

“After my dad passed, in 2017 — and Ben was very, very close with him — it changed something in us, I think,” Damon told journalist Chris Wallace. “You start to see the endgame, and you start to feel like, ‘I want to make every second count. I don’t want to fritter away time anymore.’ ” So, 25 years after Good Will Hunting, they (along with Nicole Holofcener) wrote The Last Duel in 2021. Damon’s wife told him afterward, “I haven’t heard you laugh like that in ... years.”

Now they’ve made it official. “If we don’t make [each other] a priority, it’s just not going to happen,” Damon told the Associated Press. In 2022, they launched a production company because, as Affleck put it, “How much life do we have left, and what are we going to do with it?”

Ken Jeong & Randall Park

Challenge each other to succeed, and to do good

Ken Jeong & Randall Park are shown in a photo illustration
Ken Jeong and Randall Park first got to know each other as up-and-coming comedians in the early 2000s.
WENN/Alamy

Before Community and The Masked Singer made Ken Jeong, 56, a household name, and Fresh Off the Boat brought Randall Park, 51, into millions of living rooms, they were young comics in an industry that kept Korean American actors mostly on the sidelines. Their friendship became a steady light in a business that usually left them in the dark.

They met in the early 2000s, when Park was running a small stand-up show at North Hollywood’s HaHa Comedy Club and booked Jeong — then still a full-time physician. Jeong had impressed Park so much onstage that it was “mind-blowing and upsetting” to learn he was equally brilliant in medicine. Park says he studied Jeong’s act, taking cues from his timing and presence. Years later, Jeong told Time he couldn’t have pursued his sitcom career on shows like Dr. Ken if it hadn’t been for Fresh Off the Boat.

When Jeong received his star on the Hollywood Walk of Fame last fall, Park made a speech and pulled back the curtain just enough to show how much that mutual support has mattered. He kept things light, opening with a jab about Jeong’s sitcom paychecks, but then shifted to speak about his friend’s deep commitment to others — mentoring young Asian American artists and joining KultureCity, a nonprofit that supports children on the autism spectrum, including Park’s daughter. “He has the biggest heart,” Park said. “He’s always been there for me in my times of need, and he truly brings me so much joy.” When Jeong spoke at the event, all those years of laughter gave way to emotion. “I did not want to cry,” he said, smiling through it. “I did not want to cry.”

Tina Fey & Amy Poehler

Take that next leap, but always together

Amy Poehler & Tina Fey are shown in a photo illustration
Tina Fey and Amy Poehler first met in 1993 when they both worked at an improv theater in Chicago.
Todd Owyoung/NBC via Getty Images

In improvisational comedy, “Yes, and…” means you accept your partner’s idea and build on it. For Tina Fey, 55, and Amy Poehler, 54, it’s more than a stage rule; it’s how they live. Since meeting at Chicago’s ImprovOlympic theater in 1993, they’ve instinctively answered each other’s leaps, not just with agreement but with “I see you and raise you.”

They clicked instantly (That lady is hot stuff, Poehler recalled thinking) and quickly upped the comedy ante with a two-woman sketch show about policewomen named Powderkeg and Shortfuse. It ran for exactly one performance, but their friendship was set. When Fey joined Saturday Night Live a few years later, she didn’t leave her comedy partner behind — she lobbied until Poehler joined too, and together they “yes, anded” their way to becoming the first female coanchors of “Weekend Update.”

“Sometimes Tina is like a very talented bungee-jumping expert,” Poehler once said. “All it takes is Tina to softly say, ‘We can do this, right?’ and I suddenly feel like I can jump off a bridge.” Teaming up also meant sidestepping competition. As Poehler told AARP, “Tina and I don’t have sisters, so we haven’t been trained to fight.” Their team mentality has only deepened with age. They were apprehensive about hosting the Golden Globes from opposite coasts during the pandemic (“I kept having these technological stress dreams,” Poehler admitted), but leaning into the bit got them through. “We figured, ‘Why don’t we get back in there and try it?’ ” Poehler said. Midshow, Fey, in New York, reached for Poehler — “Oh, I’ve missed you, my love” — as another hand from the split screen “nuzzled” Poehler in L.A.

With another “Sure, we’ll do it,” they launched their “Restless Leg” tour in 2023, marking more than 30 years of friendship — and never saying never — together. As Fey famously put it: “Say yes, and you’ll figure it out afterward.”

Snoop Dogg & Martha Stewart

Exit your bubble and enter theirs

Snoop Dog and Martha Stewart are shown in a photo illustration
Snoop Dogg and Martha Stewart first met in 2008 on Stewart's show lifestyle-themed TV show.
Jason LaVeris/FilmMagic

Friendship can flourish when you step outside your own mold. When Martha Stewart, now 84, and Snoop Dogg, 53, made cognac mashed potatoes and “green” brownies on The Martha Stewart Show in 2008, audiences were baffled. What could a domestic goddess and a West Coast rap legend possibly have in common? “I don’t even understand it,” Snoop said at the time. “I just have fun.”

Since then, they’ve built a bond by continually leaving their comfort zones — Snoop potting tomatoes, Stewart praising pot — without trying to change each other. “We really are BFFs,” Stewart told AARP in 2023. “It’s an education to get into the brain of someone like him.” As Snoop puts it: “We willing to try things.”

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And the older they get, the more their mismatch makes sense. “He helps me with my stuff, and I help him with his stuff,” Stewart said on The Tonight Show. Sure, that includes business — they’ve teamed up for game shows, launched a line of wines, even gotten fake tattoos of each other’s faces for a commercial. But the loyalty runs deeper. When Rolling Stone left Snoop off its 50th-anniversary rap retrospective, Stewart is said to have erupted: “That was bulls---!” When gossip blogs hinted at a feud last year between Stewart and fellow food icon Ina Garten, Snoop shut it down: “Martha don’t fall out with people.”

Are they different? Absolutely, and that’s the point. In Stewart’s 84th-birthday video, she’s glamorous in black evening wear while Snoop, beside her, puffs a joint and gently kisses a cupcake. One glam, one gangsta — together, they’ve never looked better. True friends expand your world without asking you to shrink. “When we come together,” Snoop once said, “it’s a natural combination of love, peace and harmony.”

Martin Short & Steve Martin

Through all the laughs, let your care shine through

Martin Short & Steve Martin are shown in a photo illustration
Martin Short and Steve Martin first worked together on the 1986 hit comedy "The Three Amigos."
Michael Buckner/Variety via Getty Images

For Steve Martin and Martin Short, lovable roasting has been like oxygen in a 40-year bond extending from Three Amigos to Only Murders in the Building. Take their signature eulogy bit from SNL: “Wow! Not much of a turnout,” Martin, 80, sniffs at Short’s imaginary funeral. Short, 75, interrupts: “There are so many great things I could say about Steve Martin, but this hardly seems the time or place.”

Hilarious, yes, but their friendship thrives less on snark than on knowing when to cut the act. When Short’s wife, Nancy, died of cancer in 2010, Martin didn’t deflect — he composed “The Great Remember” on the banjo, a tender instrumental piece. They later staged a conversation about aging that morphed into their ongoing comedy tours. And when Martin became a first-time father at 67, Short (a father of three) showed up with genuine support and, OK, maybe a few punch lines about Martin being the oldest guy at the playground.

“With Steve, there’s a level of comfort I don’t have with anyone else,” Short said of Martin a few years back. “We can be goofy together, we can be serious together, and it all just works.” Martin is just as mushy. Short is “kind of the perfect person,” he has said. “If Marty can’t come, you cancel the party.”

Their friendship is a master class in male vulnerability cloaked in laughter. They vacation together with their families, play cribbage on tour buses and claim they’ve never had a single argument. “You have a perspective at this age that it’s not forever,” Short said recently. “So to feel great and healthy and have loved ones around you, you appreciate it.”

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