Prior to this agreement that'll expand their business dealings, the road to a relationship had already been paved after the streamer set up two projects with Appian Way, including the Martin Scorsese-directed and DiCaprio-starring feature Killers of the Flower Moon, in addition to the thriller series Shining Girls. The latter of those two projects will be executive produced by DiCaprio (and also star The Handmaid Tale's Elisabeth Moss). Also note that Apple ponied up $200 million for Flower Moon, which will allow them to stream it while Paramount Pictures distributes it in theaters worldwide.
In the past Appian Way has produced a bunch of DiCaprio films, including: The Aviator, Shutter Island, The Revenant, and The Wolf of Wall Street. Noting their other DiCaprio-less credits, Variety writes that they were also responsible for features Out of the Furnace and The Ides of March, and documentaries: Cowspiracy, Sea of Shadows, And We Go Green, Ice on Fire, and Virunga. As for TV, they're behind the miniseries Grant on the History Channel, and they're also working on The Right Stuff for Disney Plus.
The Hollywood Reporter adds that Appian Way previously had a three-film deal with Paramount. Prior to that they were housed with Warner Bros.
They've never had a deal for TV shows until now.
This news also represents the latest push by Apple to acquire some big name people to help them produce content. Before DiCaprio they had also reached business agreements with Julia Louis-Dreyfus, Justin Lin, Idris Elba, Kerry Ehrin, Jason Katims, and Oprah Winfrey.