The Chair Company (2025): Cast, Plot, Release Date, Review & Where to Watch – HBO’s Dark Comedy of Office Shame and Conspiracy

Embarrassment at work is something most of us can relate to—but what if it spirals into something bigger, darker, and stranger than anyone could imagine? That’s the premise of The Chair Company, HBO’s brand-new comedy series starring Tim Robinson, premiering October 12, 2025, exclusively on HBO Max. With eight episodes running weekly through November 30, this offbeat workplace satire promises to blend absurdity, paranoia, and biting humor in a way only Robinson and his longtime collaborator Zach Kanin can deliver.

🪑 A Joke That Becomes a Conspiracy

At the heart of the series is William Ronald Trosper (Tim Robinson), a man whose life is upended after an embarrassing workplace incident. What starts as shame slowly unravels into a bizarre journey, as he stumbles upon a far-reaching conspiracy tied to his company.

The tone is sharp, awkward, and hilariously uncomfortable—something fans of I Think You Should Leave will instantly recognize. As one of the characters quips: “This isn’t about the chair anymore, is it?”

The show leans into Robinson’s brand of comedy—painfully awkward, satirical, but layered with genuine commentary on corporate culture and the absurdity of modern work life.

🎭 Meet the Cast

The Chair Company is stacked with a diverse cast blending comedy and drama talent:

• Tim Robinson as William Ronald Trosper – the anxious, accident-prone lead.

• Lake Bell as Barb Trosper – William’s grounded but skeptical partner.

• Sophia Lillis as Natalie Trosper – his sharp, witty daughter.

• Will Price as Seth Trosper – the family’s voice of reason caught in chaos.

• Joseph Tudisco as Mike Santini – a co-worker who might know more than he lets on.

• Lou Diamond Phillips as Jeff Levjman – the wild card whose presence hints at the conspiracy’s scale.

It’s an unusual mix, pairing Robinson’s oddball energy with Bell’s dry wit and Lillis’ rising star power, while Phillips adds gravitas to the comedy chaos.

🎬 Behind the Scenes

The Chair Company is created by Tim Robinson and Zach Kanin, continuing a collaboration that began on Saturday Night Live and grew into cult hits like Detroiters and I Think You Should Leave.

With Adam McKay (The Big Short, Succession) and Andrew DeYoung (Friendship, 2024) executive producing, the show is backed by heavy-hitters who know how to balance satire with cinematic flair.

Episodes run about 30 minutes, making it a perfect weekly binge of cringe, laughs, and conspiracy theories.

📺 Streaming Details

• Release Date: October 12, 2025

• Episodes: 8 (weekly until November 30)

• Where to Watch: Exclusively on HBO Max

• Genre: Comedy / Satire

📝 Final Thoughts

The Chair Company takes the smallest, most humiliating office moments and stretches them into an epic, laugh-out-loud conspiracy tale. With Robinson at the helm, expect awkward silences, bizarre tangents, and the kind of comedy that makes you say: “I shouldn’t be laughing at this… but I am.”

For fans of Succession’s biting workplace satire or I Think You Should Leave’s absurdist edge, this series might just become HBO’s next cult classic.

👉 Are you planning to watch The Chair Company when it drops on HBO Max this October?