1. Pete's Proposition
Season five saw the return of the slimy, manipulative, creepy Pete that we had all come to know and hate in season one. As a junior partner, Pete's biggest responsibility throughout this season was to reign in and keep Jaguar. The account would catapult the agency into the "big leagues," doing business with the luxurious car companies. The plot thickens, so to speak, in episode 5x11 when in the midst of bidding for a contract, Ken and Pete meet with a rep from Jaguar, whose requests fall outside the realm of business-as-usual: he wants to spend the night with Joan. Big leagues, indeed. Pete seizes the opportunity for an opportunity and approaches Joan about the proposition. His demeanor is transparent and desperate, and he knows it. He slowly walks into her office, disappointed, hoping that she could help the agency in some way because they're going to lose the account. Joan's immediate reaction is of offended shock, concealed humiliation and thinly veiled disgust for Pete. He peppers the proposition by likening her to Cleopatra when Joan points out the obvious that it's prostitution. Pete: "She was a queen. What would it take to make you a queen?" Joan: "I don't think you could afford it." Pete leaves, offering up the emptiest apology known to man: "This was an act of desperation. I hope I haven't insulted you. That's all that matters to me." The twist to this entire episode? Joan accepts the offer after careful consideration of finances, and leverages it to be made partner with a 5% shareholder position.