YMMV / The Crazy Ones

• Harsher in Hindsight: With Robin Williams' death so soon after the show's run, it's quite painful to remember all those jokes about Simon's worry that he won't live to see any grandkids Sidney might give him.
  • One episode has a woman reading a poem about hanging yourself while Robin Williams' character listens silently.
  • A late series episode is all about a client and close associate of Simon's suddenly dying, triggering his own feelings of mortality and ending with a speech where he remarks that the legacy of a father is the love of his daughter. Though much of this is played for laughs, it's also incredibly tragic, particularly given Williams' own immense love for his daughter and the reality of what happened to Williams mere months after this episode was made.
• Hilarious in Hindsight:
  • The clients that want Simon to sell an erectile dysfunction pill, which Robin Williams once did on Whose Line Is It Anyway?.
  • Simon's apparently random quip about a "gay Brad" in "The Spectacular", when Gordon Lewis, played by a Brad (Garret), is revealed to be gay.
• Hollywood Homely:
  • Sydney is treated like this a lot. She's often described as "normal" attractive and has trouble dating while she's played by the lovely Sarah Michelle Gellar
  • The models, led by Adriana Lima, in "Models Love Magic" reveal that they are part of a book club and are seen knowledgeably critiquing Franz Kafka's "The Metamorphosis". Meanwhile Sydney, who had been holding onto the belief that she is at least intellectually superior to women who are much more beautiful than her, is completely lost and sheepishly reveals that she doesn't know any of Kafka's work.
• Ho Yay: "Models Love Magic" has a particularly rare case of one of them actually being gay with Simon and Gordon.
  • Zach and Simon
  • Zach and Andrew, of course.
• Les Yay: Syndey and Lauren. The outtakes for "The Face of a Winner" even has Sarah Michelle Gellar gleefully make out with Amanda Setton.^note Something she seems to make a habit of doing
• Nightmare Fuel:
  • Andrew's sisters circumcised him themselves when the doctor who was supposed to do it didn't arrive. Fortunately, they apparently "did a fantastic job", but the kind of recklessness they display is horrifying.
  • Also, Andrew’s sister Elaine is a serial rapist who rapes men while they’re too drunk to know it happened the next day, and no-one seems to care.
• Unfortunate Implications: Invoked in-universe about the women-only holiday Sydney was going to. Lesbian overtones are one thing, but then she brings up the "Exploration Of The Flower" seminar.
  • In the same episode, Andrew is forced to change into a tracksuit leftover from a contract with Pringles, leading to this gem:
  "Can we go inside? My butt says "Grab a Can", and that right there is a leather bar."

---