Best friends Sam and Tim work on an advertising pitch for Chrysler, but they run into problems with the company's vice president of marketing.
After a client inspires Tim and Sam to work less and live more, the guys buy a motorcycle instead of the production van they need then outsource their work to the building's overzealous (and underqualified) security guard, Ned.
Sam starts dating a local councilwoman who thinks he's a prostitute; Sam's new lifestyle inspires Tim and his wife to try role-playing.
Tim and Sam try to convince an old Motown legend to sing a jingle for a local wig company ad that they're producing; Tim has to come to terms with his own singing skills.
Sam struggles to come up with a worthy speech to make at his father's 60th birthday party; Tim is elated that an off-duty clown is in attendance and presses him to perform.
A new tech company moves into Tim and Sam's building, disrupting their daily flow; Sam lies to Tim about his plans after developing a crush on one of the women from the new company.
After getting fired by a furniture store client, Tim and Sam try to make an ad for the store's main competitor, who struggles on camera.
When their employees threaten to quit due to a lack of health insurance, Tim and Sam try to collect the money that they're owed from previous jobs.
Tim's father unexpectedly returns from the insane asylum under suspicious circumstances; Tim and Sam struggle to create a great tagline for a department store ad that caters to husky boys.
Tim and Sam discover that the Chrysler executive they ran over has led a terrible life ever since; after appearing in one of the guys' ads, Pistons legend Rick Mahorn gets serious about acting.