Angelina Jolie on Robert De Niro: “He Sees the Bigger Picture”

By the mid-2000s, Angelina Jolie was one of Hollywood’s most bankable stars. Fresh off an Oscar win for Girl, Interrupted (2000) and global recognition for the spy comedy Mr. & Mrs. Smith (2005), she was in high demand. But when Robert De Niro cast her in his 2006 directorial effort The Good Shepherd, Jolie found herself in a very different kind of spy story—one less about explosions and gadgets, and more about the quiet devastation of a life lived in secrets.

Jolie played Clover Wilson, the conflicted wife of CIA officer Edward Wilson (Matt Damon). It was a role that demanded restraint rather than spectacle, embodying a woman “stopped by her time,” as Jolie later put it. Yet despite the challenges, she came away with deep admiration for her director.

“To do anything with De Niro is a dream come true,” she told The London Net in 2006. When the interviewer suggested that not all actors transition smoothly into directing, Jolie was quick to defend De Niro. “That’s true. But Bob sees the bigger picture. He sees beyond the characters; he sees every detail, including the history and the people in the story. He’s obsessive about detail and research and works really hard.”

A Director Obsessed With Detail

Jolie wasn’t alone in her assessment. Damon, who shouldered the film’s heavy lead, echoed her sentiments: “That’s what Bob is great at and why he’s a great actor and a great director. He micro-manages all those little details and he doesn’t stop until all those little details are in the right place.”

That rigor was central to The Good Shepherd, a period drama exploring the birth of the CIA and the personal costs of a life lived under its shadow. Unlike action-heavy spy thrillers, the film leaned into the psychological burden of secrecy, the sacrifices made in family life, and the moral ambiguities of intelligence work.

De Niro, speaking to CNN around the film’s release, praised Jolie’s performance, noting that she challenged his vision of Clover with her own interpretation. The divergence, he said, ultimately strengthened the character: “I was very happy with what she did. She did a wonderful job.” Later, he went further, calling Jolie one of the actors he’d “love to work with” again.

The Actor’s Director

Jolie has since credited De Niro with shaping how she views filmmaking. In a later interview with IGN, she reflected that she learned from him what it meant to be an “actor’s director”—someone who understands the nuances of performance because they’ve been in front of the camera themselves.

That approach, of course, is deeply informed by De Niro’s decades-long collaborations with Martin Scorsese, which taught him to value character over spectacle. Like his earlier directorial outing A Bronx Tale (1993), The Good Shepherd emphasized inner turmoil and moral complexity over easy answers.

A Mutual Admiration

For Jolie, working under De Niro’s direction was not just another job but an education. Her comment that “Bob sees the bigger picture” captured the respect she holds for an artist whose obsession with detail extends beyond performance into the very fabric of storytelling.

And for De Niro, the admiration was mutual—he saw in Jolie an actor unafraid to push back, to challenge, and ultimately to deepen the material.

Though The Good Shepherd may not have achieved the cultural impact of other espionage classics, it remains a thoughtful examination of the costs of loyalty, secrecy, and power—brought to life by a director with an unyielding eye for detail, and an actress who recognized that vision immediately.

Would you like me to frame this piece as part of a larger trend of actors-turned-directors (like Clooney or Affleck) to give it a broader cultural hook, or keep it tightly focused on Jolie and De Niro’s collaboration?