Jul 4, 2026 · 56 min · 11 segments
In 1995, Dale Wheatley had just written and produced Don's Plum starring his friends Leonardo DiCaprio and Tobey Maguire. The film was quickly snapped up for a 3-picture deal. But then Leo decided he…
Dale WheatleyGuest
Julian MorgansHost
Leo basically swore he was gonna destroy us, uh, and that's what he went on to do, and, and, and destroy the movie as well.

And so Leo went on an absolute rampage, and from that day forward, my entire Hollywood experience changed, I mean, overnight.

So all that got blocked, and, you know, it was the end of my dreams on that day really.

Hey, I'm Julian Morgans, and you're listening to What It Was Like, the show that asks people who have lived through big dramatic events what it was like.

This week we're going to Hollywood, and I have to say these kinds of stories have a special place in my heart.

I actually studied film at university, and in a roundabout way, that's how I got into podcasting.

Now this week I'm speaking with a man named Dale Wheatley, who grew up in Vancouver and then moved to LA where he landed in with a crowd that included Leonardo DiCaprio and Tobey Maguire.

Now, this was before Romeo and Juliet, it was before Titanic, and Leo wasn't a household name, but he was coming up in the world, and this circle of friends, they all partied together, they ate together, they slept on each other's couches, and then they made a film together.

It was a hyper low budget indie film called Don's Plum, and it was scripted and produced by Dale and starring all of Dale's friends, including Leo and Tobey Maguire.

Danny DeVito's production company wanted to sign them up for a three-picture deal, and Dale suddenly found himself living his childhood dream.

But then Leo and Tobey had a change of heart, and they set about doing everything that they could to crush the film and dismantle Dale's friendships.

This is a story about power and about doing everything right and still having it not work out.

I think it's a pretty sad story in a beautiful way, and it's a fascinating glimpse behind the biggest, glitziest curtain in the world.

And one last thing just before we get started, you're gonna hear us reference Dale's book a few times, which is a memoir of this period of his life.
Read the full transcript.
Create an account to read the whole episode, search across every transcript, and follow the shows you care about.