Leonardo DiCaprio is one of Hollywood’s biggest — and most acclaimed — leading men. Considered one of the best actors of his generation, he’s also highly bankable, with his movies usually making big bucks at the box office. What if we told you he has spent over two decades trying to keep one of his early films buried, though, for fear of what it might do to that bankability? And what if we told you that film also starred Spider-Man?
A young star on the rise
Back in the mid-‘90s, DiCaprio was a young star on the rise. He spent his days acting in projects such as The Basketball Diaries and his nights partying with his friends in Los Angeles, many of whom were also actors. In fact, one of his best pals was Tobey Maguire, who would become the first big-screen Spider-Man in 2002, and Kevin Connolly, who is now best known as Eric “E” Murphy in HBO’s Entourage.
A boom period for indie cinema
The ’90s was also a boom period for independent cinema. In this era, a batch of young directors decided they weren’t going to wait to be given the keys to Hollywood’s kingdom by major studios. Instead, they went out and made their own films — on extremely limited budgets — and then sold these pictures for big money after gaining buzz at places like the Sundance Film Festival.
A creative, low-key approach leads to success
Success stories of this period included Quentin Tarantino’s Reservoir Dogs, Richard Linklater’s Slacker, Kevin Smith’s Clerks and Doug Liman’s Swingers. These films all heavily relied on dialogue rather than visual spectacle, which made the movies appear more “real” than typical Hollywood pictures. Many of these indies took a slice-of-life approach, so it often felt like you were simply watching groups of friends hanging out.
Why don’t we try making one of these?
At some point, DiCaprio and his buddies looked at each other and realized they were already a group of young Hollywood types hanging out in L.A. If independent movies were proving both creatively fulfilling and commercially viable… why didn’t they try making one? Over the course of six shooting days in ’95 and ‘96, that’s just what they did — and the result was Don’s Plum. It wound up tearing the group apart.
Dale Wheatley enters the picture
The origin of the project came from Dale Wheatley, a Canadian filmmaker who moved to Hollywood to make it big and wound up becoming part of DiCaprio’s circle of friends. As he told newspaper The New York Post in 2019, “I was obsessed with success. I didn’t come to L.A. to stare up at the Hollywood sign — I wanted to make something of myself.”
Leo gets behind Don’s Plum
Wheatley collaborated on the idea for Don’s Plum with Tawd Beckman and David Stutman, who became producers on the project. When they took the idea to DiCaprio and he agreed to come on board, they knew they were onto something. Wheatley said, “Having that guy in your corner obviously means that the rest are probably going to follow him. That’s exactly what happened. Everybody got excited about the experiment.”
The project comes together
The concept of Don’s Plum was simple — a group of four friends meet at the titular restaurant every Saturday night, each with a different girl accompanying them, and talk about life. The creative team secured $70,000 funding from Beckman’s father Jerry and hired a former child actor — R.D. Robb — as director. DiCaprio convinced Maguire, Connolly, and their other buddy Scott Bloom to play the main roles, and the project was off to the races.
Initial signs are incredibly positive
Initially, everything seemed to go to plan, with Wheatley being stunned at how naturally funny and compelling the cast were while improvising dialogue that wasn’t on the page. He revealed that on DiCaprio’s second — and last — day of shooting, he told him how overwhelmed with gratitude he was. He said, “I just can’t believe what he has done for us. And I’m expressing that, and I give him this really big hug.”
“We pulled it off”
After the shoot, Wheatley looked at the 30 hours of material they’d gathered and was incredibly happy. He said, “Nobody expected that we could pull off the kind of movie that deserves a full-on theatrical release, a big festival run. We pulled it off, and you know, we finally got there.” Beckman also told The New York Post, “There was this idea that we’re going to make millions of dollars from this film.”
Leo gets cold feet
Unfortunately, this was when everything started to go wrong. When DiCaprio realized Wheatley intended their little experiment to be a full-length movie, he began to worry — he had only ever envisioned it as a short film. Wheatley revealed, “Leo was like, ‘Guys, I don’t want this to be a feature film. I can’t afford a bad feature film to go out right now. That’s just not going to work for my career.’”
Wheatley understood Leo’s concerns
To his credit, Wheatley understood why DiCaprio — on the verge of his breakout success with Romeo + Juliet and Titanic — would feel this way. He admitted his friend “was concerned, and look, he had good reason to be concerned. He’s a rising star. He’s becoming one of the great actors of our time and he can’t be having joint missteps along the way. We were empathetic to that.”
A premature announcement lays the foundations for disaster
Wheatley, Beckman, Stutman, and Robb truly believed they had the makings of a great indie film, though, on par with anything else making waves in Hollywood at the time. According to Wheatley, he talked DiCaprio into allowing them to cut the project as a feature to see if their faith in the material was well-founded. But when Wheatley and the other producers publicly announced the film in Variety magazine, it laid the foundations for disaster.
Leo had done a complete 180
DiCaprio was reportedly furious at this announcement, but Wheatley claimed he changed his tune when he attended a screening at the MGM Plaza in L.A. He said, “Suddenly he was jumping out of his chair. He’s high-fiving all of our friends — Leo had done a complete 180.” Beckman backed up Wheatley’s story, claiming, “Leo was literally rolling on the floor laughing.”
Tobey throws a spanner in the works
At this point, Robb was signed by DiCaprio’s talent agency CAA because they saw a screening of Don’s Plum and loved it. The team began receiving offers to distribute the film, including from Miramax, which at the time was the studio most associated with indie cinema. But disaster finally came when Maguire — and his agent — saw the film. They did not react like DiCaprio.
Differing opinions on Maguire’s problem with the film
Maguire reportedly believed the edgy, profane film had the potential to ruin his burgeoning career. Still, Beckman told The New York Post that he believed there was something else at play — jealousy of DiCaprio’s magnetic performance. He said, “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.”
A worry that reality and fiction would blend
There was also a worry that audiences would conflate the characters Maguire and DiCaprio played in the movie with who they were in real life. If that was the case, they wouldn’t come across well, given how juvenile and misogynistic some dialogue exchanges were. Beckman actually understood, saying, “it is so free-flowing, and it seems so natural, that an audience is gonna look at that, look at DiCaprio, look at Maguire and say, ‘Oh, that’s who they are.’”
The group already had a rep
At the time, DiCaprio and his buddies were already fighting against negative public perception thanks to a New York Magazine article from 1998. Entitled “Leo Prince of the City,” writer Nancy Jo Sales had given the group a rude nickname — which wound up sticking — and painted them as frat-house party boys. She also alleged Don’s Plum “may provide an inadvertent glimpse behind the curtain shrouding the secret society of Leo and his friends.”
Wheatley believes Maguire thought the film would fail
This might give insight into why Maguire would have reservations, but perhaps doesn’t explain the severity of what he did next — at least according to Wheatley. He alleged, “Tobey Maguire believed Don’s Plum would just be a pile of crap, we weren’t going to succeed, Leo’s going to say ‘no.’ But that’s not what happened. There’s no way to make it stop now unless he creates a villain, and I am the mark for that.”
Maguire allegedly blows his top
Wheatley claimed Maguire accused him of piggybacking on his and DiCaprio’s status as stars on the rise. In response, Wheatley explained that he’d announced the film publicly in Variety to show he and the other producers were capable of generating buzz for the film themselves — without solely relying on their famous stars. This allegedly enraged Maguire, who “lost his mind” and screamed, “I want Don’s Plum to burn!”
Maguire makes a serious accusation
Maguire’s next move — again, according to Wheatley — was to tell DiCaprio that Wheatley and Robb had attempted to turn the press against him in order to ensure release of Don’s Plum. Wheatley said he begged Maguire not to do that, adding, “I don’t even know the first thing that would even mean to pit the press against Leo. He is my friend. You are my friend. We love you guys. We made this movie together.”
Leo turns against the film
Sadly, Wheatley believes his former friend “was there to destroy the movie.” In the end, Maguire seemingly got what Wheatley claims he wanted — he turned DiCaprio against the movie. In a 1996 interview for Detour magazine, DiCaprio said, “I had a friend who I did a short film with recently who slandered me. I was trying to do a favor for him. His name is R.D. Robb.”
“I just did it as a favor, you know?”
DiCaprio continued, “It’s scandalous. It was originally a short film, and then he tried to make it into a feature. I worked one night on it, and I heard all this stuff about how he was going to pit the press against me if I didn’t go along with him and do the feature. I just did it as a favor, you know?” Once these quotes were out there, Don’s Plum was dead in the water.
Wheatley’s prospective career is left in tatters
In 1998 it was reported by New York Magazine’s Sales, “The film was pulled from Sundance. Miramax is no longer interested in investing.” Wheatley told The New York Post in 2019, “All of my relationships are completely gone, I’ve got a dead film, I can’t get anywhere. I am blacklisted.” He added, “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.”
A legal battle ensues
The ugly situation turned even uglier when Wheatley and three other producers sued Maguire and DiCaprio for $10 million. They accused the superstar actors of waging a campaign to bury Don’s Plum by making “potential buyers, distributors and others afraid to offend DiCaprio,” if they agreed to distribute the film. Naturally, the two actors counter-sued and a settlement was eventually reached.
A settlement is reached – with conditions
As part of the settlement, DiCaprio and Maguire agreed that the film could be distributed around the world — except in the U.S. and Canada. They also had provisos — namely that a few lines of particularly offensive or personally embarrassing dialogue be cut from the film. In the end, the film did see release in some European territories and Japan, but most of the profits went to paying the producer’s legal fees.
Leo and Tobey’s careers hit the stratosphere...
In the wake of the entire debacle, DiCaprio went on to star in Titanic — then the highest-grossing movie of all time — and a host of other hits, before finally winning his first Academy Award in 2016 for The Revenant. Maguire starred in director Sam Raimi’s Spider-Man trilogy, then returned to the role in 2021 for Spider-Man: No Way Home — currently the sixth-biggest movie of all time.
…while everyone else stays firmly rooted to the ground
By contrast, instead of the millions of dollars and thriving career he’d hoped for, Wheatley made a paltry $180 from Don’s Plum. He worked as a salesman, and said, “I was living a life I dreaded for the most part.” Stutman didn’t have any kind of Hollywood career either. In fact, he was sued by Beckman’s father to recoup his $70,000 investment. The elder Beckman settled for the rights to the film.
Free Don’s Plum
By 2014 though, Wheatley had taken all he was going to take. He created a website called freedonsplum.com and uploaded the entire movie there, along with an emotional — and lengthy — open letter to DiCaprio. He began, “I have not spoken to you since you successfully blocked our film Don’s Plum from being seen by the audience for whom it was intended.”
Bullying, censorship and abuse of power
Wheatley continued, “You might be the only actor in the history of American cinema who has publicly and unapologetically shamed his director and then went on to destroy his work. And we just might be the only living filmmakers in America to have their film banned in the USA and Canada. This letter is about so much more than just a movie. It’s about bullying, censorship, and abuse of power.”
In his letter, Wheatley very clearly blamed Maguire for inciting everything, but then took aim at DiCaprio for blindly believing his version of events. He wrote, “In a single night in 1996 you made a series of hasty and wildly irrational decisions that hurt a lot of people.” He added, “Had you just taken time to listen to reason, you would have found that Tobey Maguire was using you for his own mysterious purposes.”
Spitting in the face of independent film
The letter continued, “Had you actually taken the time to look at the facts, and not just listened to Tobey, you would have continued to support Don’s Plum. But instead, you allowed yourself to get swept up in a witch hunt that destroyed art and careers.” He added, “You and Tobey Maguire spat in the face of independent film and the community that helped get you where you are today.”
A bittersweet compliment to Leo
Wheatley called Maguire’s accusation of pitting the press against DiCaprio “the fallacy that destroyed everything.” To him, it robbed the world of DiCaprio’s performance, which he again praised in the letter, writing, “I don’t think there is a living actor today that could have done what you did in Don’s Plum in a single night.” He also wrote, “Appearing in Don’s Plum was the most generous favor you could have done for your friends.”
“He played you like a pawn”
At the core of the matter, Wheatley strongly believed, “This problem, and this letter, exists because of Tobey. He played you like a pawn. He pitted you against your own friends, and then hid behind you while you trampled all over a perfectly good independent film.” Wheatley wanted DiCaprio to reconsider his stance and stop blocking Don’s Plum from a full release.
A takedown notice is issued
The movie remained on the website in all its glory for 16 long months, but it was eventually taken down. A statement in its place read, “We have removed your video titled Don’s Plum, previously available at Vimeo, in a response to a takedown notice submitted by Leonardo DiCaprio and Tobey Maguire pursuant to the Digital Millennium Copyright Act.” Clearly, Wheatley’s letter hadn’t had the desired effect.
A sad Hollywood tale
All in all, Don’s Plum is a sad example of what can happen when friends have a falling out, and how that can be compounded when fame, money, and art is also involved. In the end, it has simply deprived cinephiles of something they would be super-curious to watch. Wheatley might even be right in saying the movie is genuinely good — many critics who have seen the picture have said as much.
A good vehicle for Leo’s innate flair
In 2016 Charlie Lyne of The Guardian wrote, “Don’s Plum is as good a vehicle as any for DiCaprio’s innate flair as an actor. Freed from the self-consciously weighty air of his recent roles, he delivers a sparky and sinister turn seemingly without care for how he might come across.” Compared to more modern micro-managed, focus group-tested roles, Lyne found the performance “positively daring.”
What’s so shameful about the movie?
As for the supposedly offensive content that could have sunk DiCaprio and Maguire’s careers, Decider’s Joe Reid wrote, “I’d still love to know what Leo finds so shameful about the movie that he doesn’t want it seen.” He added, “It’s self-indulgent, prurient, immature, and obnoxious. We’ve all already accepted that this was Leo’s persona in the ’90s anyway. Nothing in this movie is enough to take Leo down, even a little.”
Leo’s people make their statement on the matter
DiCaprio and Maguire haven’t spoken publicly about the movie in a very long time. Yet when Wheatley’s interview with The New York Post went live in 2019, it came with a comment from DiCaprio’s publicity team that read, “The events and comments described in this story are decades-old lies fabricated by Dale Wheatley in an effort to gain publicity and unlawful financial gain.” Take from that what you will.
Wheatley continues doing everything to preserve Don’s Plum
As of 2022, freedonsplum.com is still in operation, and Wheatley is offering an HD version of the movie to anyone who emails him to request it. In a post from January 27, 2021, he wrote, “I am doing everything I can to stand up for my work and preserve Don’s Plum.” He added, “I respond to each email individually so it may take a minute, but I’ll get it to you as soon as I am able.”