Wes Anderson Only Directed Ben Stiller Once — And It Led to His Best Performance Yet

Ben Stiller can do it all, and that is becoming crystal clear in 2025 with his Apple TV+ hit thriller, Severance. Gradually transitioning to making great works behind the camera, he wasn’t always the funny man he is known as today. One of his first big breaks as an actor was in a dramatic role in Wes Anderson‘s critically acclaimed film, The Royal Tenenbaums. Starring opposite Hollywood legends Gene Hackman and Angelica Houston, Stiller’s performance is often overlooked in favor of the more flamboyant, colorful characters. But it remains his greatest role.
Released in 2001, The Royal Tenenbaums was nominated for Best Original Screenplay at the Academy Awards and hailed for its detailed, stylish examination of a dysfunctional family in crisis. Stiller’s on-screen siblings were played by some of the brightest stars at the time, Gwyneth Paltrow and Luke Wilson, and the three of them together created complex portrayals of adults haunted by their youth. Owen Wilson co-wrote the script with Anderson, and the film hinges on Stiller and Hackman’s portrayal of a father and son struggling to forgive.
What Is ‘The Royal Tenenbaums’ About?
Royal Tenenbaum (Hackman) is a middle-aged, lonely man estranged from his three children and wife. All former child prodigies, Chas (Stiller), Margot (Paltrow), and Richie (Wilson), were constantly berated by Royal, which led to their mother, Etheline (Huston), divorcing him. In the present day, none of the three children have lived up to their potential. They all still wear the same clothes they wore as children and are plagued by depression. Chas, especially, is struggling after his wife dies in a plane crash and is now raising his two sons on his own. He winds up moving back in with his mother, which causes a domino effect of Margot and Richie moving back in too. When Royal hears that Etheline’s accountant, Henry (Danny Glover), has proposed to her, he tries to break them up by creating a lie that he’s dying so he can move back in too. Bill Murray plays Margot’s husband, Raleigh, and Owen Wilson plays the Tenenbaum’s drug-addled neighbor, Eli Cash.
Ben Stiller Plays a Grieving Widower In a Rare Dramatic Performance
Anderson’s movies have always been vibrant and strange. Stiller plays one of Anderson’s most underrated misfits, Chas—he had all the ingredients to become the epitome of the American dream, but it was shattered by a series of unfortunate events, including his father. Chas wears a red jumpsuit for the entirety of the film that serves as armor for whatever disaster he believes is going to strike after the death of his wife. Stiller is instantly heartbreaking as the tragic Chas. He’s introduced alone in his apartment, watching a ticking clock, haunted by the time he’s lost with his wife. He then makes his children perform a fire drill, and through Stiller’s wild, stressed-out energy, Chas’ fear is what stands out the most.
Much of Chas’ sorrow is rooted in his father’s betrayal. From shooting him in the hand as a child with a BB gun to Chas turning Royal into the IRS as an adult because he was stealing from him, Royal’s road to redemption is based on Chas’s forgiveness. Stiller aches with anger and grief for the whole film as he isolates himself, while everyone else is quick to welcome their father back in. The ultimate warning of Chas’ unwillingness to let go of his anger, and the screenplay’s brilliance, is that he could become his own worst nightmare: his father. Royal’s development from a deadbeat dad to a caring father hinges on Stiller’s grief-stricken performance and his willingness to let go of the past.
Ben Stiller and Gene Hackman Play an Estranged Father-Son Duo on the Rocks
One of the most iconic sequences in The Royal Tenenbaums is when Royal takes Chas’ kids out for the day. It’s everything Royal wished and should have done with Chas, but chose to do it with Chas’ sibling, Richie, instead. And that led Chas to be the self-reliant, isolated man that haunts Stiller’s performance. His words are clipped, his brow is always furrowed, and his stance is always tense. Stiller’s nuanced depiction of a man drowning in depression is an unsung triumph within his filmography. The film’s beauty, then, is that it’s his father who ultimately reaches in and pulls him out of the water.

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The Royal Tenenbaums is widely considered Hackman’s last great role. Many of his great moments come in scenes with Stiller and his desperate need for forgiveness. Stiller and Hackman are an unexpectedly spectacular acting duo who match each other’s gruffness in all their bickering matches. Tough guy Hackman, who rarely showed vulnerability, shows his soft side to Stiller and elevates Stiller’s acting as well. In the chaotic wedding scene at the film’s end, Chas’s dog gets run over and killed by his neighbor, Eli. Royal comforts Chas by gifting him a new dog. Stiller then tearfully delivers the most devastating line of the film: “It’s been a hard year, Dad.” Hackman’s gentle response of “I know” is simple but sweet, and Royal’s acknowledgment of Chas’ pain is all he needed to finally heal. All Chas needed was his dad, and finally, Royal got to be one.