- Barney asks Lily to paint a nude picture of him after finding her painting of Marshall. And Ted can't find an opportune time to fire his old boss, who now works for him but still keeps undermining his work.
- Although Ted is happy that the firm's client liked his design for the Spokane National Bank making him now the boss, he doesn't like a lot of what having to be the boss entails, like the fact that most of his former colleagues, who are now his employees, dislike him solely because he is the boss. The worst part is that his former boss, the arrogant and mean spirited Hammond Druthers, is now one of those employees, although he still treats Ted poorly. Brady, one of the managing partners of the firm, recommends to Ted that he fire Druthers. Ted has every intention of firing Druthers and having fun doing it, but he begins to have mixed emotions about doing it after spending some time with Druthers and finding out about his life. Meanwhile, Barney, Ted and Robin find a nude painting of Marshall that Lily painted of him while they were in college. Beyond the embarrassment that Marshall feels especially as Barney, Ted and Robin taunt him with public exposure of the painting, the painting brings up certain feelings within both Barney and Lily, who feel they could mutually benefit from acting on those feelings.—Huggo
- Ted is trying to deal with his former boss, Hammond Druthers (he was very big in 80's and the worst boss Ted ever had in his life.. Druthers was demoted when he failed the pitch for the Spokane National Bank building), but when he can't, he decides to fire him. Before, Ted was one of the guys.. but now, he was the boss and the employees judged him on everything he did or said. The guys clammed up whenever he walked into the room. Ted was always working, even when he was not at work. Earlier, Ted would encourage people to call in sick for foo-fighters events, but now would catch people when they lied about being sick. Ted wants Druthers to be put on a different project, but the Managing Partner is an old man who tells Ted to fire everyone on the project including Druthers and Mosby (not knowing that Ted is Mosby).. he thinks Ted's last name is Crosby. Robin cautions Ted, because when she fired her makeup assistant she messed up her makeup just before the broadcast and made her look like a whore and a clown.
The first time he attempts to fire him, he is interrupted by fellow employees bearing a birthday cake for Hammond. The second time, Ted comes into the office one night and finds Hammond in boxers and a pajama shirt; his wife has left him, and he has been sleeping at the office. Once again, Ted's plan is thwarted, and he takes Hammond home to sleep on his couch.
Despite Ted's altruism of letting him stay in his apartment (sharing breakfast, tossing him extra toilet paper in the bathroom and so on), Hammond continues to belittle his ideas in the office (when Ted pitches the ideas of columns for the Atrium, Druthers calls it stupid in front of everyone). He tries to fire him again, but just as he is, Hammond is handed his divorce papers and learns that his dog is dead. Then, the employees approach with another birthday cake, since they were in Montreal during his real birthday celebration days before. Ted decides to fire him anyway, but Hammond suffers a heart attack in the process. Ted thinks he is faking it to keep from getting fired, and continues to mock him. Hammond is taken away in a stretcher. Ted convinces his co-workers that he did not cause the heart attack Everyone in the office initially hates Ted, but forgive him when he comes up with the idea of "Margarita Fridays," complete with margarita machines.
Meanwhile, Marshall is tormented by the picture Lily painted of him posing nude as a freshman at Wesleyan. Lily wanted to do a nude art study, and Marshall didn't want Lily looking at any random guy's junk. So, he posed nude for her instead. Ted, Barney, and Robin find the painting behind the piano and have the bartender hang it up behind the bar at MacLaren's. Marshall manages to snatch it away by jumping at it.
To Lily's surprise, Barney proposes that she paint him in the nude, as he was impressed by the quality of the drawing. He offers her a size-able sum of money ($5000), but Lily worries that it will upset Marshall. She talks him round by suggesting that they can use the money to spend their honeymoon in Scotland (where Marshall can connect with the Loch Ness monster, whom he lovingly calls Nessy), rather than their original plans to explore the country's caverns. Marshall later finds a more expensive castle to stay at, and tricks Barney into paying an additional $5000 by pretending to argue with Lily about painting another man in the nude. Barney is unhappy with the finished painting, complaining that Lily gave him the "Ken Doll" (not painting his genitals).
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