David Clennon as Miles Drentel; Richard Cummings Jr. as Mark Harriton; David Marshall Grant as Russell Weller; Nana Visitor as Cindy, Miles' fiance; Carly Simon as herself; Charles Barkley as himself, uncredited
Melissa gets a job shooting the cover to Carly Simon's new album while Michael struggles as the company goes under.
Terry Grossman informs Michael and Elliot that Motherland Foods is up on the block, taken over by an unfriendly Canadian corporation which means that the company is in serious danger of losing a lot of money which means that there isn't much to dole out to lowly ad agencies. Meanwhile, the guys play basketball in a corporate league (The Ad Boys) and, for the first time, we meet D.A.A., Mark Harriton, and Miles Drentel. After losing the game to D.A.A., the guys meet Mark in a bar and he asks them, in a leading way, how things are going, implying that Motherland is indeed going under.
Meanwhile, Russell Weller is somehow connected with Carly Simon and has gotten Melissa a deal to shoot her next album cover. Michael and Elliot are cut loose from Motherland, which spells near certain doom for their company. Michael and Elliot go to Miles and ask for sub work, but D.A.A. never does that and he turns them down. They go to the bank and can't get a loan, which drives Elliot into denial and Michael into depression about his responsibilities. Elliot tracks Miles down to a restaurant and is mildly obnoxious to him.
Melissa finally gets to the party where she's supposed to meet Carly Simon and it goes really well. Elliot shows up with Miles and entourage in tow, getting drunk, and making more of a mess out of himself while Miles plays him for a fool. In the shadows, Michael is getting more and more depressed about his impending failure while Melissa is finally being a success. Hope gets him to dance and it seems to help, but in the middle of it Elliot starts screaming at Miles and they practically shove each other off the balcony (boy, wouldn't that have changed the flavor of the fourth season).
Melissa oversleeps the next morning having had such a good time until Gary comes to wake her up and tell her what's been going on with Michael and Elliot. The truth is really sinking in for them and they contemplate how they can take care of their employees once the agency closes. Michael and Melissa have an emotional talk about their relationship and relative amounts of success, how Michael was always ahead of her before now. The Ad Boys play D.A.A. again and Michael plays well, hitting almost every shot. It closes with Elliot and Michael sitting silently in the deserted bleachers, Michael beginning to cry.
Michael is 5' 10" the house was probably built in 1911 the company has been around for 16 months opener clips of Melissa riding in a limo and Michael shooting the layup Craig and Walter are the company lawyers for Michael and Elliot
Carly Simon's classic "You're So Vain" is belted out by Polly Draper into a pot lid (of all things) while Melissa takes the call from Carly Simon's management.
"No, you should do an album. Rod Stewart sings Carly Simon." --Melissa on Ellyn's rendition of "You're So Vain"