Tim and Sam, two low-level Detroit ad men, try to secure a big ad campaign with Chrysler, resulting in disaster. Meanwhile, their assistant Lea takes on a hot-tub commercial on her own. Guest starring Jason Sudeikis and Steve Higgins.
Tim and Sam approach an old Motown legend to perform a jingle for an ad campaign they are working on. Meanwhile; Tim has to come to terms with his own singing skills, or lack there of.
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, and Lea runs into trouble editing a local mirror store's ad.
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 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 chubby (husky) boys.
Detroit Pistons star Rick Mahorn gets the acting bug after appearing in an ad for Tim and Sam, who learn the Chrysler exec they'd hit with their car has been having a rough time of it ever since.
