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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
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 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?”
Next in series
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