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- The guys court legendary newscaster Mort Crim to be the celebrity spokesperson for one of their clients, and Ned ramps up security in the building.
- Sam re-records an old jingle he sang with his ex after it causes friction in his new relationship, and Tim finds out that he isn't well-liked on the internet.
- Cramblin Duvet hits a hot streak, and Sam and Tim help Sheila find a lawyer after she gets a DUI.
- 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.
- Tim's mom convinces him to give his difficult brother a job at Cramblin Duvet, and Sam unexpectedly bonds with Chrissy.
- 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.
- Sam and Tim decide to play dirty after Doner starts stealing their clients.
- 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.
- Sam starts acting blacker in a bid to impress his new girlfriend, Tim gets roped into spending time with a widower, and Chrissy has trouble hitting it off with a new coworker.
- 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.
- Tension builds between Sam and Tim after Sam acts in one of their commercials, and Sheila's relationship with Lea becomes strained after she makes an off-color joke.
- An adventuresome client inspires Sam and Tim to ditch the office and cruise around on their newly purchased motorcycle.
- Sam starts dating a local councilwoman who thinks he's a prostitute. Tim and his wife are inspired by Sam's new lifestyle and try role-playing.
- 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.
- Sam takes the reigns as grill master at the Duvet family reunion, and Tim considers whether he might be too hard on Sam's girlfriends.
- 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.
- 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.
- An errant football to the head while eating pizza lands the guys a Little Caesars ad.
- Sam discovers he might be a father which puts the future of Cramblin Duvet in jeopardy.