At dinner, Freddy is trying to explain that he was nervous about the pitch, but Roger immediately tells him about the six-month plan. It would seem a lot more merciful if he were actually being truthful here. Don pipes up that it'll be full salary, and Freddy will come back and they'll see where they are. I'm surprised Don is actively participating in this charade, but it's not like Freddy believes it anyway as he pleads his case; "Clients love me! I keep up with them!" He's probably not wrong in thinking that boozing and schmoozing is the value he's been bringing, but the pissing problem unfortunately threatens the efficacy of that as well. Roger: "There's a line, Freddy. And you wet it." Hee. Freddy points out that it can't be that serious if they're joking about it, and besides, they used to have much worse drunks at the place, including Roger's own father, who "drank more than the two of you put together." That's not actually possible, is it? But that seems to mean that Roger inherited his position from his father, which explains not only the age difference between him and Bertram but also the fact that he doesn't seem to have any advertising skills at all. Freddy tells some war stories about Roger's dad, and Roger admits that his father admired Freddy, but this entire conversation is Freddy pushing a rock up a hill like Sisyphus, and when he comes to realize it, he accepts his fate, saying he's got a great book, and maybe he'll start over in a new town. Roger suggests the three of them make a night of it, and calls the waiter over for another round of drinks and a colostomy bag.
Later, the three of them are looking pretty lit up as they negotiate with a bouncer to let them in someplace shady-looking. Reinforcing that idea is the fact that the bouncer looks like he could eat an African elephant raw and still have room for dessert. Roger can't remember the password, so after some funny drunken banter that amuses everyone except the gorilla in front of the door, he applies a twenty to the situation, which gets them a ride downstairs. On the way, he remembers the password, and is like, "Son of a bitch!" Heh.
They arrive in an obviously illegal casino, wherein some of the women are not letting Marilyn's death affect their hair, and sit down at a table. Freddy spies a famous boxer (Floyd Patterson, although his name isn't mentioned here), and after Roger orders them a round, Freddy muses, "Pete Campbell, huh? I would have never thought I was in his way." No offense, Freddy, but you're even a bigger drunk than I thought if you haven't noticed how desperately Pete wants to be on the Creative side.