The Crazy Ones

The Crazy Ones

Simon Roberts: The half-hour comedy series was created to showcase the unique comic talents of Robin Williams, who first brought his wild and zany brand of comedy to the television screen in the late 1970s. In The Crazy Ones, Williams plays an outrageous ad executive who describes himself as someone who can sell anything. In his own self-told back story, Simon, played by Williams, proclaims he “could sell frapuccinos to Starbucks and clouds to God.”

Williams’ character is a troubled soul in spite of his rambunctious and lively antics at work. His life has been spent living on the edge and is reflected in multiple failed marriages, of which daughter Sydney is a product of, and has been in and out of rehab.

In an effort to get to know his daughter, whom he finds very effective in building his agency’s reputation, he hires her to work for him. The effects prove a little unbalancing for Simon. As the head of a very lucrative advertising company, he is used to people who work for him agreeing with all of his ideas and concepts; not so with Sydney.

The role of Simon is Robin Williams’ swan song as a television character. Sadly, Mr. Williams passed away before beginning the filming of Season 2 of the series. Watch The Crazy Ones online to experience this epic show and enjoy the brilliance of Robin Williams.


Sydney Roberts: The role of Simon’s daughter is played by stoic comedic actress Sarah Michelle Gellar. Her ability to play it straight opposite Robin Williams’ loud and hectic performances makes her perfect to play the down-to-earth realist the character of Sydney is. She is strong. The result of a divorce, she has a tendency to not trust relationships and value work and friendships over love. Even though she spent her childhood with her mother and had little contact with her busy father, she didn’t blame him for his absence. It was from that viewpoint that she developed her own hard working attitude.

Sarah has a long list of accomplishments, including movies and television. She is most well-known for her early role as Buffy Summers in the Buffy the Vampire Slayer television series.


While The Crazy Ones is predominately about Simon and Sydney’s relationship, there are several very important cast members that complete the advertising agency’s roster. These players make the show more of an ensemble than a star vehicle, and add to the weekly laughs.

Zach Cropper: Zach is a copywriter with a smooth, enchanting personality. He is a copywriter with a strong relationship with Simon, both of whom seek each other’s approval both in work and life. Zach is played by James Wolk whose recurring roles in notable television shows such as Political Animals, Shameless, Lone Star and Mad Men make him immediately recognizable.

Andrew Keanelly: A past love of Sydney’s, Andrew is a laid back, intelligent member of the group. While Sydney sees Andrew as a close friend with whom she once had a relationship, Andrew still carries a torch for his former lover. In his efforts to win her over, he also constantly seeks Simon’s validation, hoping that it will sway Sydney’s opinion of him. Andrew is played by funny man Hamish Linklater, well-known for his rolls in the HBO series The Newsroom, and in his recurring role on The Good Wife.

Lauren Slotsky: Smart, if a little timid, Lauren is Simon’s assistant. Played by beautiful Amanda Setton, a long-time soap opera actress who appeared in One Life to Live also has many television and movie roles to her credit.

Several guest stars appear regularly on The Crazy Ones. Brad Garret, famous for his role as the lumbering, unappreciated brother in Everybody Loves Raymond works in the accounting department of the agency and appears often to criticize Simon’s spending habits and what he considers as a lack of professionalism on the part of the marketing department.

Singer and songwriter Josh Groban also appears regularly on the series. No stranger to acting, musician Groban has appeared in several movies and series before The Crazy Ones.

A surprise highlight of the show is the humorous Fred Melamed who plays himself. A regular voice-over actor, Fred often complains about his role in life and the direction of his work as he adds his vocal talents to the commercial projects being created by the agency.

Season 1 of The Crazy Ones has 22 episodes with plenty of charm and outstanding comedy. In spite of only airing for one season, it still managed to be nominated by the Critics’ Choice Awards for best actor in a comedy series. The series also received three nominations for a People’s Choice Award, one of which was one by Sarah Michelle Gellar for favorite actress in a new TV series. You can enjoy all of the wonderful characters on this series when you watch The Crazy Ones online.