With a friendship spanning decades, Leonardo DiCaprio holds Tobey Maguire in extremely high regard.

Titanic’s Leonardo DiCaprio and Spider-Man’s Tobey Maguire’s bromance has been going strong for decades now; an impressive feat given Tinseltown’s reputation for decimating even the closest of friendships.

The twosome first met back in the 80s, long before they shared the stage in the 1993 coming-of-age drama, This Boy’s Life. Since then, they’ve shared adventures on multi-million-dollar yachts, starred side by side in Baz Luhrmann’s 2013 adaptation of F. Scott Fitzgerald’s The Great Gatsby, and gone above and beyond to build a friendship seemingly impervious to the glitz and glamour of Tinseltown.

With such an enduring bond, it’s quite evident that DiCaprio holds Maguire in extremely high regard. But could the trust between the two A-listers be so implicit that DiCaprio would risk ruining one of his closest friends’ filmmaking career based solely on Maguire’s word?

Leonardo DiCaprio And His Infamous Group Of Friends Starred In The Forgotten 90s Movie, Don’s Plum

Leonardo DiCaprio and Tobey Maguire have been friends long before they both ascended to the dizzying heights of the Hollywood A-list. Though the two had been bumping into each other at auditions constantly from as early as the 80s, they might have never become such close pals were it not for DiCaprio’s sheer determination to recruit Maguire into his inner circle.

“I literally jumped out of the car,” DiCaprio told Esquire of his pursuit of Maguire in a 2014 interview. “I was like, ‘Tobey! Tobey! Hey! Hey!’ And he was like, ‘Oh, yeah — I know you. You’re… that guy.’ But I just made him my pal. When I want someone to be my friend, I just make them my friend.”

But Maguire wasn’t the only potential A-lister DiCaprio had set his sights on. As his friendship with the Spider-Man star blossomed, DiCaprio moved to organize around himself a roving band of former child stars and aspiring actors who’d become his surrogate family for the next decade or so.

The group originally comprised the likes of Lukas Haas, Harmony Korine, David Blaine, R.D. Robb, Jay Ferguson, and Kevin Connolly, but kept growing as DiCaprio willed. Among its lesser-known members was aspiring filmmaker Dale Wheatley, who fell in with the infamous posse shortly after relocating from Canada to Los Angeles.

Wide-eyed and thirsty for success, it wasn’t long before Wheatley convinced DiCaprio and the rest of the Posse to take part in a film project he hoped would kick-start his stalling filmmaking career.

Starring DiCaprio, Maguire, and other members of the posse, the project, which eventually came to be known as ‘Don’s Plum,’ followed the exploits of a group of 20-somethings who rendezvoused at a diner every Saturday night, dissecting their daring escapades with women in raw and unapologetic detail.

Tobey Maguire Was Not Happy With His Portrayal In Dale Wheatley’s Don’s Plum

Originally intended to be a short film, the project was shot in about two days, leaving Leo with ample time to jet off to Florida to film his 1996 drama, Marvin’s Room.

However, while the Titanic star was away, Dale Wheatley and his team of amateur filmmakers, which included David Stuntman and Tawd Beckman, managed to piece together 30 hours of additional footage and decided to upgrade the project into a feature film.

“Nobody expected that we could pull off the kind of movie that deserves a full-on theatrical release, a big festival run,” Wheatley would later say of the film in a 2019 interview with the New York Post. “We pulled it off, and you know, we finally got there.”

Though hesitant at first, DiCaprio eventually came around to the idea of turning the project into a feature after Wheatley and his team managed to pull together a screening at MGM Plaza. However, there was one member of the posse who wasn’t as delighted with the film’s sudden and unexpected success; Tobey Maguire.

“Tobey Maguire believed ‘Don’s Plum’ would just be a pile of cr*p, we weren’t going to succeed, Leo’s going to say ‘no’ … but that’s not what happened,” Wheatley told The New York Post of the Spider-Man star in 2019. “There’s no way to make it stop now unless he creates a villain … and I am the mark for that.”

What followed was a rather explosive blowout at Dale Wheatley and R.D. Robb’s apartment, where Maguire accused Wheatley and his team of trying to take advantage of DiCaprio’s burgeoning star power to advance their careers.

“Tobey loses it and comes completely undone,” Wheatley recalled in a 1998 legal deposition according to Collider. “And he starts screaming, ‘I want Don’s Plum to burn!’ And it was just rage, pure unadulterated rage.”

Did Tobey Maguire Really Cause A Falling Out Between Leonardo DiCaprio And One Of His Best Friends?

Not long after, the posse gathered once more, this time with DiCaprio in the mix. Once again, Maguire came out swinging, accusing Dale Wheatley and his team of attempting to stir a publicity nightmare for DiCaprio.

According to Wheatley, DiCaprio’s demeanor became increasingly icy during the meeting, and it wasn’t long before he had his own expletive-ridden blowout. “My f**king agents run this town, and they run Sundance and believe me that movie’s not gonna be in Sundance,” the Titanic star allegedly declared according to Collider.

Not long after, Dale Wheatley’s project, which had, mere weeks prior, attracted interest from heavy hitters like Miramax, was pulled from the Sundance Music Festival. With his filmmaking career floundering, Wheatley attempted to fight back with a $10 million lawsuit, only to be silenced by a settlement that banned the film from ever being shown in the US and Canada.

Years later, Wheatley has yet to resurrect his filmmaking career; a misfortune he blames solely on Maguire. “They weren’t the Pussy Posse, they were the bully posse. These guys are terribly intimidating with their power and their influence,” Wheatley later said of DiCaprio and Maguire in his 2019 interview with the New York Post. “Maguire destroyed my life. He destroyed my career. For the last 20 years I’ve been living in the rubble of the destruction that he created.”