MomSkoop
True friendship stands the test of time, especially in the spotlight of fame. While Hollywood relationships often fizzle, some star-studded friendships have flourished for decades, proving that genuine connections can survive the pressures of celebrity. These long-lasting bonds offer us a glimpse into what makes friendships endure – shared experiences, mutual respect, and unwavering support through life’s ups and downs.
1. Oprah Winfrey and Gayle King
Their friendship began in 1976 when they were young journalists working at a Baltimore TV station. During a snowstorm, Oprah offered Gayle a place to stay, and that night of shelter blossomed into 45+ years of sisterhood.
Through Oprah’s rise to media mogul status and Gayle’s own successful career, they’ve remained each other’s rock. “She is the mother I never had, the sister everybody would want, the friend everybody deserves,” Oprah has said of Gayle.
They’ve vacationed together, celebrated milestones, and defended each other publicly, showing that true friendship survives fame, fortune, and everything in between.
2. Matt Damon and Ben Affleck
Childhood buddies from Cambridge, Massachusetts, Matt and Ben grew up just blocks apart. Their breakthrough came when they co-wrote and starred in “Good Will Hunting,” winning an Oscar for Best Original Screenplay in 1998.
Despite Hollywood’s competitive nature, their friendship has flourished for over 40 years. They’ve supported each other through career highs and personal struggles, including Ben’s battles with addiction and Matt’s family challenges.
Recently reuniting for “The Last Duel” and forming a production company together, they’ve proven that boyhood friends can become lifelong creative partners while maintaining an authentic connection despite fame’s pressures.
3. Jane Fonda and Lily Tomlin
Meeting on the set of “9 to 5” in 1980, Jane and Lily formed an immediate connection that has spanned over 40 years. Their chemistry was so natural that producer Marta Kauffman created “Grace and Frankie” specifically for them, resulting in Netflix’s longest-running original series.
Beyond their on-screen partnerships, they’ve stood together for social causes, from women’s rights to environmental activism. “I don’t know what I would do without my women friends,” Fonda has often remarked.
Their friendship showcases how professional collaborations can evolve into deep personal bonds that only strengthen with age and shared purpose.
4. Jennifer Aniston and Courteney Cox
From “Friends” co-stars to real-life besties, Jennifer and Courteney’s bond has outlasted marriages, breakups, and Hollywood’s fickle nature. Meeting in 1994 when cast as Rachel and Monica, they quickly became inseparable off-screen too.
Courteney served as Jennifer’s maid of honor, while Jen is godmother to Courteney’s daughter Coco. “We’ve known each other nearly 30 years. We’ve been through everything together,” Jennifer shared in a recent interview.
Their friendship represents the rare Hollywood relationship that grows stronger with time, with regular vacations together and unwavering support through career changes and personal heartbreaks.
5. Ian McKellen and Patrick Stewart
These British acting legends first worked together on the X-Men franchise, but their friendship blossomed during their 2013 Broadway performances in “Waiting for Godot” and “No Man’s Land.” Spending months rehearsing and performing together created a bond that transcended their professional lives.
Patrick asked Ian to officiate his wedding to Sunny Ozell in 2013, cementing their extraordinary connection. Their playful social media photos touring New York together delighted fans worldwide.
Despite their serious theatrical backgrounds, they share a mischievous sense of humor and deep mutual respect. “He’s one of the most brilliant actors,” McKellen has said of Stewart, “but more importantly, one of my dearest friends.”
6. Michelle Williams and Busy Philipps
Their friendship ignited on the set of “Dawson’s Creek” in the early 2000s, when Michelle was dealing with intense media scrutiny and Busy joined as a newcomer. Through life’s darkest moments, including the tragic death of Michelle’s former partner Heath Ledger, Busy remained steadfastly by her side.
For years, Busy was Michelle’s consistent red carpet date at award shows, showing how their bond transcended Hollywood’s typical fair-weather friendships. “She’s proof that the love of your life does not have to be a man! That’s the love of my life right there,” Michelle once said about Busy.
Their friendship exemplifies how finding your person can happen anywhere, even on a teen drama set.
7. Tina Fey and Amy Poehler
Comedy’s dream team met at Chicago’s ImprovOlympic in 1993, where instructor Charna Halpern noticed their instant chemistry. “They were just instantly brilliant,” she recalled. Their friendship flourished through their SNL years, where they revolutionized Weekend Update as the first female co-anchor team.
Beyond professional collaborations like co-hosting the Golden Globes and starring in films together, they’ve maintained a friendship based on mutual respect and admiration. “We don’t see each other very often, but when we do, we’re so happy,” Amy has shared.
Their bond shows that true friendship doesn’t require constant contact—just authentic connection when you’re together.
8. Paul Newman and Robert Redford
Hollywood’s golden duo first partnered in 1969’s “Butch Cassidy and the Sundance Kid,” creating cinematic magic that extended into a 50-year friendship. Though they only made two films together (adding “The Sting” in 1973), their off-screen bond remained unshakable until Newman died in 2008.
Known for practical jokes and mutual respect, they balanced stardom with genuine connection. “We never had an argument, never had a falling out,” Redford recalled fondly. Their friendship was built on shared values beyond acting—both created charitable foundations and valued privacy despite their fame.
After Newman’s passing, Redford said simply, “I have lost a real friend.”
9. Snoop Dogg and Martha Stewart
Perhaps the most unlikely friendship on our list began when Snoop appeared on Martha’s show in 2008 to make mashed potatoes. Their chemistry was immediate and genuine, surprising viewers with their easy rapport despite vastly different backgrounds.
Their friendship flourished into a cooking show, “Martha & Snoop’s Potluck Dinner Party,” and numerous brand partnerships. Martha has defended Snoop through controversies, while he speaks of her with tremendous respect.
“She’s the big sister I never had,” Snoop has said. Their bond proves that authentic friendships can bridge any gap—whether it’s age (30 years), culture, or life experience—when built on mutual appreciation and the joy of sharing good food.
10. Cameron Diaz and Drew Barrymore
Before becoming “Charlie’s Angels” together in 2000, Drew and Cameron had already formed a friendship when 14-year-old Drew served coffee to 16-year-old Cameron at a Los Angeles coffee shop. This chance meeting blossomed into one of Hollywood’s most enduring friendships.
Through marriages, divorces, children, and career changes, they’ve remained constants in each other’s lives. “We’ve experienced birth, life, death, marriage, divorce—highs and lows, work, boyfriends, friends, travel—there is nothing we haven’t done together,” Drew has shared.
Cameron was one of the first guests on Drew’s talk show, where their genuine affection and inability to stop giggling together charmed audiences.
11. Stevie Nicks and Tom Petty
Rock royalty Stevie Nicks idolized Tom Petty before they ever met, even asking him to write her a song. Though initially reluctant, Petty eventually gave her “Insider,” launching a friendship that lasted until he died in 2017.
Their musical collaboration on “Stop Draggin’ My Heart Around” became a hit, but their behind-the-scenes bond was even more significant. Petty helped Nicks through addiction struggles, while she considered him her musical mentor.
After performing together at London’s Hyde Park just months before his passing, Nicks wrote: “My heart will never get over this.” Their friendship showed how admiration can evolve into genuine connection when rooted in mutual respect and creative understanding.
12. Leonardo DiCaprio and Tobey Maguire
Meeting as child actors at auditions in the late 1980s, Leo and Tobey formed an instant connection. “I literally jumped out of my car and was like, ‘Tobey! Tobey!’,” DiCaprio recalled of spotting Maguire on the street after an audition. “He was like, ‘Oh yeah, I know you. You’re… that guy.'”
For over 30 years, they’ve supported each other through Hollywood’s ups and downs. They finally worked together in 2013’s “The Great Gatsby,” fulfilling a long-held dream.
Their friendship has weathered fame, relationships, and the passage of time. They still vacation together on Leo’s infamous yacht trips, proving that childhood bonds can last even in Hollywood’s changeable environment.
13. Betty White and Mary Tyler Moore
Television legends Betty White and Mary Tyler Moore first connected on “The Mary Tyler Moore Show” in the 1970s, where Betty played the man-hungry Sue Ann Nivens. Their on-screen chemistry translated to a real-life friendship that lasted until Mary died in 2017.
Despite their different personalities—Mary was more reserved while Betty was famously outgoing—they maintained a bond built on mutual respect and shared experiences as pioneering women in television. They supported each other through personal tragedies, including the deaths of their husbands.
“Mary and I had the best times together,” Betty reflected after Mary’s passing. Their friendship reminds us that workplace connections can develop into lifelong bonds.