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|Portrayed by||Matt Long|
|First appearance||Public Relations|
|Final appearance||The Summer Man|
|Employer||Sterling Cooper Draper Pryce (freelance)|
Joey and Don do not appear to get along, going so far as for Joey to call Don a drunk when he forgot his keys in the office and Don to make snide remarks to his face about the amount of work he does around the office. ("Christmas Comes But Once a Year") ("The Chrysanthemum and the Sword")
Joey appeared shocked during the Life cereal meeting, in which a drunk Don pitched terrible slogans to a client. ("Waldorf Stories)
While working on the Samsonite account with Danny Siegel and Stan Rizzo, Joan Holloway remarks about the mess they've created. Joey jokingly remarks that "although I am paid less, I am still not a janitor" before shrugging and walking off, leaving Danny and Stan to clean up the mess. ("The Suitcase")
Ken Cosgrove attempted to buy a candy bar from the vending machine, and while it was being dispensed the candy got stuck. Joey attempted to reach in (he has the smallest wrist) but only ends up losing his watch in the machine as well. After this failed attempt at reaching the stuck candy bar, Stan and Joey started to shake the vending machine violently, which made a loud ruckus. Joan was not happy with this and after being called "mom" by Joey in retaliation to her demands to get back to work, she asked to speak to him in private. While alone, he responded to her demands by insinuating that all she did was walk around looking like she wanted to be raped. She then kicked him out of her office.
Because of re-work necessary for the Mountain Dew account, Don requested that Joey be hired full time for a few weeks, to Joan's objections. Joey later had a meeting with Harry, where Harry mentioned that he could get him a job in Hollywood. Joey subsequently remarked to Peggy that Harry was hitting on him, calling him a "fairy".
After drawing a lewd picture of Joan giving fellatio to Lane. Peggy brought this to the attention of Don, who told her to do what she thought was necessary, including firing if she felt like it. She requested a private meeting with Joey, telling him to apologize. When he refused, she fired him. ("The Summer Man")