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.
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An adventuresome client inspires Sam and Tim to ditch the office and cruise around on their newly purchased motorcycle.
Sam accidentally becomes a prostitute, and Tim comes down with a bad case of colitis.
An old Motown legend is approached to perform a jingle for a local wig company ad that Tim and Sam are producing, which forces Tim 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. Guest starring Keegan-Michael Key.
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. Guest starring Cecily Strong and Michael Che.
Tim's father, "Big Hank,” unexpectedly returns from the insane asylum under suspicious circumstances. Tim and Sam struggle to create with 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.
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