It’s still weird to think about. Robin Williams on a network sitcom in 2013 felt like a fever dream, but in a good way. CBS had this massive opportunity, a workplace comedy set in a high-stakes Chicago ad agency, and they populated The Crazy Ones cast with an absurd amount of talent. You had a legend, a rising star from Buffy, and a bunch of character actors who have since become household names. It should have been a decade-long run. Instead, we got 22 episodes and a "what could have been" legacy that still stings for fans of fast-paced, improvisational humor.
The show focused on Roberts & Roberts. Simon Roberts, played by Williams, was the eccentric genius—the kind of guy who would hire a giant duck for a pitch just because it felt right. His daughter, Sydney, played by Sarah Michelle Gellar, was the grounded, anxious anchor trying to keep the firm from drifting into chaos. Looking back, the chemistry wasn't just scripted; it felt like a genuine passing of the torch, or at least a very expensive, very funny family therapy session.
Robin Williams and the Lightning in a Bottle
Robin Williams didn't just play Simon Roberts. He was the engine. After decades away from series television—his last regular gig being Mork & Mindy—everyone wondered if he could still do the 22-episode grind. He could. Honestly, he did it better than most people half his age.
What made his performance in The Crazy Ones cast so distinct was the restraint. David E. Kelley, the show's creator, famously wrote scripts that were "Robin-ready," meaning they had the bones of a scene but left massive gaps for Williams to riff. If you watch the blooper reels—which are arguably as famous as the show itself—you see the cast literally vibrating with the effort of not breaking character. Williams was a kinetic force. One minute he was doing a pitch for McDonald's, the next he was improvising a song with Kelly Clarkson (who had a hilarious guest spot in the pilot).
But there was a sadness there, too. Or maybe just a deep, resonant humanity. Simon Roberts was a man who knew his best years might be behind him but refused to stop swinging for the fences. It was meta. It was beautiful. It was Robin.
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Sarah Michelle Gellar: More Than a Straight Man
It’s easy to overlook Sarah Michelle Gellar when she’s standing next to a comedic supernova. That’s a mistake. Gellar's Sydney Roberts was the soul of the show. She had to play the daughter who was simultaneously embarrassed by her father and desperately seeking his approval. It’s a tough tightrope.
Gellar brought this frantic, Type-A energy that perfectly counterbalanced Williams' chaos. She wasn't just the "straight man" in the comedic duo; she was a comedic force in her own right, especially when Sydney’s own neuroses started to leak out. You’ve probably seen her in Buffy or Cruel Intentions, but this was a different Gellar. She was vulnerable. She was funny. She was the only person on earth who could tell Robin Williams to shut up and make it feel like a loving family moment.
The Supporting Players Who Rounded Out Roberts & Roberts
A show like this lives or dies by its bullpen. The Crazy Ones cast featured James Wolk as Zach Cropper, the charming, smooth-talking copywriter. Wolk has this Kennedy-esque charisma that makes you want to buy whatever he’s selling, which is perfect for an ad man. His bromance with Simon was one of the unexpected highlights of the series.
Then there was Hamish Linklater as Andrew Keanelly. Linklater is a master of the "uncomfortable silence." As the art director, he played the perpetual underdog, the guy who was brilliant but constantly overshadowed by the bigger personalities in the room. His comedic timing is dry—so dry it’s practically parched. It worked perfectly against the more "theatrical" energy of the Roberts duo.
And we can't forget Amanda Setton as Lauren Slotsky. She was the assistant who was probably smarter than everyone else in the building. Setton played her with a deadpan Brooklyn edge that grounded the show's more whimsical flights of fancy.
Why the Chemistry Worked (And Why It Failed)
Why did this show get canceled?
Honestly? It was expensive. Very expensive. And the ratings were... okay. Not great. Just okay. In the 2013-2014 season, "okay" wasn't enough to save a show with a movie-star payroll. But the chemistry was undeniable. Unlike many sitcoms that take a season or two to find their "voice," The Crazy Ones cast clicked from the pilot.
They felt like a real agency. They felt like people who had spent too many late nights eating cold pizza and staring at font choices.
- The Improvisation: The show used a "two-take" method. One for the script, one for the riffs.
- The Guest Stars: From Josh Groban to Brad Garrett, the show leveraged Robin’s Rolodex to bring in top-tier talent.
- The Setting: Chicago wasn't just a backdrop; the city's advertising history (think Leo Burnett) was baked into the DNA of the show.
The Legacy of a Single Season
When Robin Williams passed away in 2014, The Crazy Ones became his final television legacy. It’s a bittersweet watch now. You see a man who was clearly giving everything he had to the craft, surrounded by a cast that adored him. Sarah Michelle Gellar has spoken frequently about how much Williams meant to her, describing him as the father figure she always wanted.
The show tackled some surprisingly deep themes for a 22-minute sitcom. It looked at the fear of irrelevance. It looked at the burden of genius. It looked at how hard it is to build something that lasts in a world that only cares about the next "big thing."
If you go back and watch episodes like "The Face of a Nation" or "March Madness," you see a show that was just starting to find its emotional depth. It wasn't just about the jokes; it was about the people. The advertising world was just the playground.
Where to Find the Cast Today
If you’re looking to scratch that itch, the members of The Crazy Ones cast have stayed busy.
James Wolk went on to lead Zoo and turned in an incredible performance in Watchmen. Hamish Linklater has become a staple in Mike Flanagan’s horror universe, notably giving a powerhouse performance in Midnight Mass. Sarah Michelle Gellar took a bit of a break but returned with Wolf Pack and continues to be an entrepreneur.
But there’s something about seeing them all together in that glass-walled Chicago office that feels special. It was a specific moment in TV history when a network tried to capture lightning in a bottle by letting a legend run wild.
How to Appreciate The Crazy Ones Now
If you want to dive back into the world of Roberts & Roberts, don't just binge the episodes. Look for the "outtakes" specifically. They offer a masterclass in comedic timing and show the genuine bond between the actors.
- Watch for the Background Details: The production design was top-notch, featuring real-world ad industry Easter eggs.
- Focus on the Physical Comedy: Robin Williams was a master of using his entire body, and even in his 60s, his energy was unmatched.
- Check the Streaming Status: The show occasionally pops up on platforms like Hulu or Prime Video, though it’s sometimes hard to find due to music licensing.
The best way to honor the show is to recognize it for what it was: a brief, bright spark of creativity that reminded us why we fell in love with these actors in the first place. It didn't need ten seasons to make an impact. It just needed one.