Robert De Niro’s ‘The Good Shepherd’ Was Meant to Be a Directing Comeback, but It Ended Up as His Last

Robert De Niro is one of the few actors whose filmography reads like a history of modern American cinema. He has worked with some of the best-known directors for decades, and he founded TriBeCa Productions with Jane Rosenthal in 1989. In 2002, the two also launched the Tribeca Film Festival.

Directing has always been a smaller part of his story. His first film behind the camera was 1993’s ‘A Bronx Tale’, a coming-of-age crime drama in which he also acted. It was made on a $10 million budget and was well received, but De Niro went back to acting afterward.

It took De Niro 13 years to return to the director’s chair. ‘The Good Shepherd’, released on December 22, 2006, follows Matt Damon’s Edward Wilson, a fictional counterintelligence officer, from 1939 to 1961 as the CIA develops around him. Angelina Jolie plays his wife, while De Niro appears as General Bill Sullivan.

The film was a huge step up in scale. Far Out notes that the film was made on a budget of $80 million, compared with the $10 million for his debut, though other reports put the figure higher. Eric Roth wrote the screenplay, and the running time was 167 minutes.

The project had a long history. It had been in development since 1994 at Francis Ford Coppola’s American Zoetrope, and Leonardo DiCaprio was once attached to star. When DiCaprio left because of ‘The Departed’, Damon stepped in. Morgan Creek eventually financed the picture.

That backstory adds weight to the pressure De Niro described. According to Far Out, the experience left him a nervous wreck. He explained that as you get older you gain confidence in some areas but not in others, and that he was worried every day while making the film.

Critics were divided when the film arrived. The Rotten Tomatoes consensus called it ambitious and confidently directed but ultimately tedious and self-serious. Other reviewers admired Damon’s stillest, most internalized performance and De Niro’s insistence on accurate detail.

At the box office, the film opened in fourth place with about $9.9 million, behind ‘Night at the Museum’. It went on to earn about $100.3 million worldwide. That was roughly break-even against its reported budget, and it did not become the big awards contender many had hoped for.

De Niro reportedly wanted to make a sequel. Paste Magazine noted that he hoped to follow the film up with a second story about Wilson, though it is hard to see where the character could have gone next. That sequel never materialized, and the director’s chair has stayed empty since.

Instead, De Niro has continued to work as an actor. He played Bernie Madoff in HBO’s ‘The Wizard of Lies’ in 2017, and he reprised comedic roles such as the one in ‘Meet the Parents’ in its sequels. A critic writing in 2015 even wondered whether ‘The Good Shepherd’ was a last attempt to make the kind of film that better suited his sensibilities.

Twenty years on, the film has found defenders. Paste argued that it holds up as a political critique, and some viewers on Letterboxd praise its patient, subtle style. Others still find it slow. That split is part of why it remains a talking point.

It also shows how even legends struggle with doubt. De Niro’s comments suggest that directing demands a kind of confidence that acting does not. Whether he ever steps behind the camera again is unknown, but his second film remains a fascinating chapter.

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