Matt Damon Said He Outclassed Robert De Niro In Leonardo DiCaprio’s Snubbed Gem Hiding On Streaming

Explore how Robert De Niro’s challenging directorial debut in The Good Shepherd shaped careers including Matt Damon and canceled sequels.

Left Image Via Universal Pictures , Right Image Via Warner Bros.

The Good Shepherd, a 2006 American spy film, was produced and directed by Robert De Niro.

The lead cast includes Matt Damon, Angelina Jolie, and De Niro himself.

Initially, Leonardo DiCaprio was cast for the lead role, while Damon was not even the first choice.

In an interview, De Niro himself admitted this, saying (via Digital Spy, published December 25, 2006),

Leonardo DiCaprio was originally going to do it, but he had scheduling problems and it got so complicated.

I said I had to move on quickly because I had all the machinery of the movie moving forward.

Seems like it became a really good opportunity for The Martian actor to grab a role that changed Hollywood for him.

Quipping in a quote (via IMDb), Matt Damon said,

I learned a lot of things I didn’t know and I remembered a lot of things I’d forgotten and that “disappearing” into work for ten years and working constantly… You can get into some bad habits.

The film earned $100 million (via Box Office Mojo) worldwide.

But, on its way to success, the film faced several challenges while also teaching each person working on the film something new.

Key Facts
The Good Shepherd

Director
Robert De Niro

Cast
Alec Baldwin, Tammy Blanchard, Billy Crudup, Keir Dullea, Martina Gedeck

Box Office Collection
Domestic: $59,952,835
International: $40,314,030
Worldwide: $100,266,865

IMDb Rating
6.7/10

Rotten Tomatoes Rating
56%

How Robert De Niro’s Hardest Shoot Became His Greatest Teacher

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For Robert De Niro, The Good Shepherd was an intimidating experience. But it also shaped his career.

In an interview with CNN (via Far Out Magazine, published September 13, 2025), he confessed the same.

The Good Shepherd was such a daunting project that I had to think about it moment for moment, day by day… As a director, [I] try and guide things in the way that I like to see movies go.

For an actor, a set of things is already taken care of.

He just needs to follow a vision already sought by someone.

But when the actor steps into the shoes of a director, it demands a presence that should be felt and acted upon.

De Niro’s experience, though unsettling, has taught him a lesson, which he applies to date in his projects.

Was The Good Shepherd Sequel Cancelled Despite Having Robert De Niro’s Backing?

Billy Crudup in The Good Shepherd | Credits: Universal Pictures.

Yes, Robert De Niro even worked with writer Eric Roth on the same.

But it was ultimately grounded.

The reason behind it is said to be the poor reception from the audience.

Originally envisioned as a trilogy, with the first sequel extending the story to 1989 and the next exploring the present day.

But after the first film’s financial failure, the trilogy never materialized.

Despite everything, in September 2012, Showtime was working on a television series around it, with De Niro and Eric Roth joining forces, but it too got stalled (via Deadline).

Do you think The Good Shepherd deserves a second chance as a series? Share your thoughts below.

The Good Shepherd is available for streaming on Prime Video (US).