The Truth Behind Hollywood's Most Enduring Friendships

Whether we're talking about Hollywood BFFs or bitter enemies, the friendships of Tinseltown have long captivated fans. We tend to mythologize celebrity friendships, imagining them closer than they probably are because they've acted in a few movies together. The truth is, many actors, like regular people, keep their work and their private lives separate. 

But there are those that defy the norms. There are some platonic partnerships that are not only made up of megastars, but have endured the test of time, and the glare of the limelight. Despite having some of the most involved careers possible, these actors have found time to share their life with a famous friend. 

While these duos are hard to miss, the true histories of their friendships are not common knowledge. These partnerships have lasted longer than you might imagine, weathered conflicts you didn't know about, and have origin stories worthy of films. Read on to discover the truth behind Hollywood's most enduring friendships.

During the awards circuit in 2017, Busy Philipps accompanied her best friend, Michelle Williams. "I'm so in love with her," Williams told reporters (via People), "She's proof that the love of your life does not have to be a man!"

The two didn't become friends until 2001, when Philipps joined the cast of Dawson's Creek, however, the relationship was apparently destined to happen. While on Philipps talk show, Busy Tonight, Williams recalled a mutual friend saying, "You guys are going to love each other. You're going to meet each other, and then, like, the world won't be the same, and it hasn't been the same for me."

The two became inseparable, perhaps most notably attending the Academy Awards together in 2006, 2011, 2012, and 2017 for Williams' nominations. Interestingly, Philipps suggested to the Los Angeles Times column Ministry of Gossip in 2011 that she was "the hex" on Williams' losses.  

Fortunately for this enduring Hollywood friendship, Williams doesn't concur. "You're just always there," Williams tearfully told Philipps on the finale of Busy Tonight (via Daily Mail). "The truth is — that you show up for all of us, all of the time. And that you are the most selfless person that I know, and it's taught me everything that I know about being a friend." Aw! And the Academy Award for cutest friendship goes to... 

Before Saturday Night Live and their subsequent films together, comedy geniuses Tina Fey and Amy Poehler met at Chicago's ImprovOlympic in 1993. According to Poehler, the two were basically set up by the co-founder of the improv training, Charna Halpern. 

"Charna took a liking to me, and me to her," Poehler wrote in her book, Yes Please (via Vulture). "She told me I was just as good as the big boys. She believed in me. She said there was another new improviser in another one of her classes whom she thought I would really like. Her name was Tina and she was like me but with brown hair."

"They were just instantly brilliant," Halpern told the New York Post. "They were not the typical women who get steamrolled by men. [They] were no shrinking violets. They were bold and ballsy and fearless." After ImprovOlympic, the two went their separate ways for a time, but they eventually rejoined forces on SNL.

According to Fey's book, Bossypants, it didn't take Poehler long at SNL to show her stripes. After Jimmy Fallon, one of the stars of the show told her he didn't like a dirty joke she was telling, Poehler didn't back down. "Amy dropped what she was doing, went black in the eyes for a second, and wheeled around on him. 'I don't f**king care if you like it.'" Fey remembered thinking then, "My friend is here! My Friend is here!"

Leonardo DiCaprio and Tobey Maguire met as kids competing on the Hollywood audition scene. DiCaprio told Esquire that he was drawn to Maguire because they grew up in similar situations. So DiCaprio made him his friend. "When I want someone to be my friend, I just make them my friend," the superstar said.

Over the years, the actors' friendship made headlines, like an unflattering 1998 New York Magazine piece which stated, "Leo always traveled with his pack of devotees, known in Hollywood circles as 'The P*ssy Posse,'" which included Maguire. Then there was their controversial 1996 film, Don's Plum, against which DiCaprio and Maguire fought a legal battle to ensure it was never released. 

According to one of the film's producers, Tawd Beckman, the film's ad-lib style risked tarnishing its star's images, but it may have been an internal competition that sank the film. "I could definitely see Maguire, as I knew him, feeling that Leo had outshined him, and that possibly being part of the motivating factor for wanting to kill this film," Beckman told the New York Post. 

Yet, competition has always been part of their relationship. According to People, Maguire and DiCaprio have competed for several roles in their careers and still remain close. "Leo and I have a lot of trust and respect for each other," Maguire said. "We have a close friendship and I definitely have an affection for [him]."

Ever since they made Charlie's Angels in 2002, Cameron Diaz and Drew Barrymore have built a seemingly unbreakable bond. Under the watchful gaze of fans, the two actresses have shared some of the biggest moments together and gushed about each other every chance they have. 

"We're like more than best friends, she's my sister," Barrymore told ET in 2018. "We have much more of that kind of relationship; we're very honest with each other. We push each other. And we've had the majority of our lives spent side by side, really going through what real life is, which is an everyday high and low, and we just have each other's backs."

One of surprising elements to this superstar friendship is that these two have known each other longer than most think. While they may have cemented their friendship on the set of Charlie's Angels, it actually began long before that. "She was actually 16 and I was 14 when we became friends," Barrymore said on Katie. "We were both, like, L.A. kids, you know. I worked in a coffee house. She was a model, and I, like, served her coffee and we had mutual friends." She then added, "She was always kind. You know, someone who looks like that, they could be, you know, have an attitude, and she was the opposite. She was friendly and goofy and really nice."

When Grace and Frankie first aired in 2015, it marked 35 years since Jane Fonda and Lily Tomlin first joined forces alongside Dolly Parton in 9 to 5. It was there that the two actresses started a friendship that would span decades. 

While on The Late Show with Stephen Colbert, Fonda, who was a producer on 9 to 5, said that she saw Tomlin's one-woman show, Appearing Nitely, and fought to get her on the film for more than a year. Since then, they've attended special events together, marched in protests, and even participated in a TED Talk on "longevity, feminism, the differences between male and female friendship, [and] what it means to live well and women's role in future of our planet."

Knowing how close they truly are, their reunion on Grace and Frankie makes a lot of sense, but it was actually quite the accident that it happened like it did. In fact, the show's co-creator, Marta Kauffman, called it a "gorgeous fluke." In an interview with IndieWire, Kauffman said that she heard whispers that the two actresses wanted to do a television show. She thought they meant on the same show, so she had her agent check if that's really what they meant.  

She then got back the reply, "They do now."  

Fans may think wrongly that every actor from Australia knows each other, but in Nicole Kidman and Naomi Watts' case, they actually do! Though she was born in England, Watts moved to Australia when she was 14 years old, and it was a move that didn't exactly thrill her. 

"I remember driving past my school, the first week we were there, and seeing how high the hems were. The kids had drawn on their uniforms and they had weird haircuts," she said in an interview with The Guardian. "This was a whole new world."

But, in that school was her future best friend. At the time, Kidman was "part of a wider gang that used to go out drinking in Sydney pubs." It wasn't until they were both cast in the 1991 Australian film, Flirting, that they became best friends. On the set of that film, Watts recalls them "gossiping for hours on overturned milk crates, waiting on scene changes."

"We already knew each other but that's when our friendship forged," Watts said to People. "We've gone through a lot together over a significant amount of time. That history binds you. We have a strong respect and love for one another."

Wes Anderson and Owen Wilson met in 1989 in a playwriting class at the University of Texas at Austin. Anderson was intrigued by Wilson's habit of reading newspapers during their seminars, and the two developed a friendship built on their love of film and film-making.

According to Interview Magazine, they soon upgraded from friends to roommates. When their landlord refused to fix some of the broken things around their dilapidated apartment, the two film students hatched a plan. They staged a robbery to force their landlord into putting their needs first. It didn't work, but it did become the inspiration for their first film and the one that helped launch them both into fame, Bottle Rocket.

But fame brings with it challenges, and it can be difficult for friends to stay close in the limelight. Back in 1999, Anderson wondered if his friendship with Wilson would struggle in Hollywood. "I mean it happens. That's the way it happens," he said in an LA Weekly interview. "The friendship that gets the most strain is the one between me and Owen. And I feel like that's as strong a friendship now as it's ever been."

Well, their friendship has lasted. They would go on to collaborate on several more movies and stand by each other during their personal and emotional struggles. Twenty Years after that LA Weekly interview, Anderson and Wilson are set to collaborate again in The French Dispatch.

When Spike Lee leapt into Samuel L. Jackson's arms after his win at the 2019 Academy Awards for Best Adapted Screenplay for his film, BlacKkKlansman, their friendship quite literally took center stage. It was a nice moment between two men who became film superstars together. 

According to Jackson's Inside the Actor's Studio interview, he and Lee met backstage when he was still a theater actor. They bonded over their Morehouse College connection and had lunch together. Years later, Lee directed Jackson in four movies across four consecutive years: School Daze, Do the Right Thing, Mo' Better Blues, and Jungle Fever. It was the latter, according to The Guardian, that helped catapult his career. 

Jackson and Lee's friendship has had some conflict as well. In a 1997 Daily Variety interview (via Jet Magazine), Lee criticized Quentin Tarantino and his film Jackie Brown, which Jackson was in, for excessively using the "n-word." Jackson then defended Tarantino at the Berlin Film Festival in 1998, quipping that "didn't get a change to vote in [the] election" that made Lee the representative of all black people. 

Things did eventually get ironed out. "Spike's wife, Tonya, and my wife, LaTanya, have been good friends for a long time," Jackson revealed in a Playboy interview (via Huffington Post). "So our wives would interact often, and we would all end up going to dinner together. Our relationship healed [from a public falling-out] over those dinners and conversations."

It was approximately 21 years between 1996's Set it Off and 2017's Girls Trip, two films that both starred Jada Pinkett Smith and Queen Latifah. But the friendship between these two multi-talented artists started even before their first together.

"I remember the first time I met her," Pinkett Smith recalled to People. "It was in Baltimore at a club where she was performing. I'd never seen anyone like her before, this female rapper named Queen Latifah. I convinced the promoter to let me introduce her." Pinkett Smith also admitted that she "had no business being in that club" because of her age, and she wasn't alone. Latifah, too, was underage. "My mother was with me," she said. "That's how young I was. I was 17." 

Both women would then go one to share a connection with Will Smith and The Fresh Prince of Bel-Air. While Pinkett Smith didn't land the part for which she auditioned on the show, she did end up marrying the star. Latifah, however, did get a spot on the show. "Will and Jada have been there my entire career," the rapper said to People. "Will gave me my first job on TV." 

Fans of Friends always wanted the cast to be friends in real life, and they got their wish, especially while the show was on the air. "Right in the very beginning," Matt LeBlanc said during the Must See TV: An All-Star Tribute to James Burrows in 2016, "[Director James Burrows] really encouraged us all to, sort of, get along, and get to know one another, and be kind to one another, and support one another, and watch one another, and help one another." 

Of the entire group, however, it seems that Jennifer Aniston and Courteney Cox remained the closest. From the start, these two had a connection. In fact, they originally auditioned for each other's roles. "I was called and asked to audition for Monica and her, (pointing to Cox) Rachel," Aniston said at the tribute. "I think we both just thought that the other was just better for the other part."

Since the show has gone off the air, more than 15 years ago as of this writing, Aniston and Cox have stayed close, really close. "I've slept in her guest bedroom a lot," Aniston said in a More magazine interview (via E! Online). "Without giving away too much of my private stuff, all I can say is she's been there for me through thick and thin."

Even though they grew up two blocks away from each other in Boston, Ben Affleck and Matt Damon were really brought together by baseball and acting. "Before Matt, I was by myself," Affleck said in an interview with Parade. "Acting was a solo activity where I'd just go off and do something, act in a little TV show or something, and no one understood it."

While attending the same high school, the two even shared a bank account, according to Damon's Off Camera with Sam Jones interview, meant for money dedicated to their acting pursuits. Years later, while at Harvard, Damon started dabbling with the script that would become Good Will Hunting. According to a Boston Magazine piece, he took the script out to Los Angeles and stayed at Affleck's place. There, the two completed it.

The rest is history. The film was an enormous success, and Affleck and Damon became stars. Like their film, their friendship has also become monumentalized, but it's not without its bumps. In a 2004 interview (via E! News), Damon said that actors shouldn't "just do blockbusters," a shot which people felt was aimed at Affleck. Later, while on SNL, Affleck returned the volley, saying "I can't seem to recall which Chekov play The Bourne Supremacy is based on. And I'm sure they'll be studying Ocean's 12 in the film classes at USC, believe me, because Ocean's 11 left so many unanswered questions."