Brad Pitt, a name synonymous with Hollywood royalty, has worked with some of the biggest stars in the industry.

But not every collaboration was smooth sailing.

Recently, Pitt revealed the five actors he found most difficult to work with, shedding light on the complexities of relationships in the entertainment world.

Number 5: Edward Norton
Pitt and Norton’s chemistry in Fight Club was electric, creating one of the most iconic films of the 1990s.

However, behind the scenes, their working relationship was far from harmonious.

Norton’s methodical and perfectionist approach often clashed with Pitt’s instinctive, laid-back style.

Norton’s tendency to take on an unofficial director role, rewriting lines and challenging decisions, created tension on set.

While Pitt remained classy and avoided public drama, he later hinted that their collaboration was a one-time event, closing the door on any future projects together.

Number 4: Gwyneth Paltrow
In the mid-90s, Pitt and Paltrow were Hollywood’s golden couple, their romance captivating fans worldwide.

They met while filming Seven and quickly became engaged.

But their relationship ended abruptly in 1997 when Paltrow called off the engagement, citing her own immaturity and Pitt’s goodness as reasons.

Their breakup was quiet but final, with Pitt choosing to distance himself completely.

Despite a playful interview in 2022, their paths have remained separate, highlighting Pitt’s preference for clean closures over rekindling old connections.

Number 3: Tom Cruise
Pitt and Cruise, two of Hollywood’s biggest stars, shared the screen in Interview with the Vampire.

While their performances were praised, the experience was anything but enjoyable for Pitt.

The stark contrast in their personalities—Cruise’s intense energy versus Pitt’s laid-back demeanor—created an underlying rivalry.

Over the years, their careers seemed to overlap in subtle competition, with rumors of tension resurfacing during projects like Salt and Ford v Ferrari.

Despite their shared success, Pitt has kept Cruise at arm’s length, avoiding further collaborations.

Number 2: Courtney Love
The drama surrounding Courtney Love’s alleged involvement in Fight Club is one of Hollywood’s most debated stories.

Love claims she was initially cast as Marla Singer but was fired after rejecting Pitt’s pitch for a Kurt Cobain biopic.

While Love has praised Helena Bonham Carter’s performance, her resentment toward Pitt remains.

The truth behind her claims is disputed, with insiders denying her version of events.

Regardless, Love’s unwavering belief that Pitt pushed her out of the film has solidified her place on his list of difficult co-stars.

Number 1: Angelina Jolie
Pitt’s relationship with Jolie was one of Hollywood’s most high-profile romances, but their divorce in 2016 exposed a darker side to their partnership.

The split led to years of legal battles, accusations, and public scrutiny.

Jolie alleged that an explosive incident on a private plane marked the breaking point, with claims of physical altercations involving their children.

The custody battle that followed fractured Pitt’s relationship with his kids, leaving emotional scars that may never heal.

Despite his efforts to stay silent and avoid further conflict, the fallout from their marriage remains one of the most painful chapters of Pitt’s life.

Through these revelations, Pitt has shown that even in the world of fame and fortune, personal and professional relationships can be deeply challenging.

His ability to navigate these conflicts with grace and professionalism speaks to his resilience as both an actor and a person.