Played by Melinda McGraw

Bobbie Barrett is the wife/manager of comic Jimmy Barrett who was hired by Sterling Cooper to do TV spots for Utz Potato Chips. Bobbie’s relationship with the agency becomes more complicated, however, when Jimmy insults a client and Don Draper begins an affair with her. Their affair is temporarily derailed when the two have a car accident while driving to the beach. Recuperating at Peggy Olson’s apartment afterwards, Bobbie sums up her strategy for making it in a man’s world: “You can’t be a man,” she advises. “Be a woman. It’s powerful business when done correctly.” Bobbie’s relationship with Don ends when he learns she’s been gossiping about him.

Played by Rosmarie DeWitt

A smart, ambitious art illustrator, Midge Daniels is a thoroughly independent career woman – much like the multitudes of women venturing into the workforce for the first time. Midge sets her own rules, rejecting the traditional idea of marriage and domesticity. Such “live in the moment” vitality makes her the perfect bedroom companion for Don. Her anti-establishment friends that come calling might be too much for Don, but she relishes in it. One night, Don Draper realizes that she and Roy are in love, and when he asks her to go to Paris, she declines.

Played by Alison Brie

Trudy Campbell is married to Pete Campbell, an Account Executive at the Sterling Cooper advertising agency. The two live on the Upper East Side of Manhattan in a Park Avenue apartment. Her father, a salesman for Vicks Chemical, helped her husband get the Clearasil account for Sterling Cooper. Trudy herself tried to help Pete with his literary aspirations by speaking with an ex-boyfriend in the publishing industry. Her actions on Pete’s behalf secured his short story a place in Boys’ Life. Trudy’s inability to get pregnant and Pete’s ambivalence about becoming a parent cause her anxiety.

Played by Mark Moses

Herman “Duck” Phillips is the former head of account services at the Sterling Cooper advertising agency. Previously, he was with Young & Rubicam in London. He’s now at Grey. In order to raise Sterling Cooper’s profile he instructed employees to land accounts with the airline, automobile, and pharmaceutical industries, with mixed results. After approaching former colleagues at the London-based Puttnam, Powell and Lowe about working there, he engineered a merger with Sterling Cooper, for which he was promised a position atop the hierarchy. His plan hit a snag when Don Draper refused to report to him, and threatened to leave Sterling Cooper. Duck has an ex-wife with whom he shares a son and daughter. He recently took possession of – and then abandoned — the family dog, Chauncey. For some time, Duck avoided alcohol; he is now drinking again.

Played by Rich Sommer

Harry Crane heads the newly created Television Department at the Sterling Cooper advertising agency. He spends much of his time at work with Pete Campbell, Paul Kinsey and Ken Cosgrove. Harry’s promotion to department head came after he proposed that the cosmetics client Belle Jolie sponsor a controversial episode of The Defenders. Although the company declined, Bertram Cooper complimented Harry’s initiative. When Harry suggested to Roger Sterling that the agency start a department devoted solely to television, Roger agreed and put Harry in charge. Although his title has changed, his salary has not increased much and he continues to share an office.

Harry is married; his wife Jennifer, who is pregnant with their first child, works at a phone company. He had a one-night stand with Hildy, Pete’s secretary, following the Nixon-Kennedy election.

Played by Elisabeth Moss

Peggy Olson is a Copywriter at the Sterling Cooper advertising agency. A bridge-and-tunnel girl from Bay Ridge, Brooklyn, she began at the firm as Don Draper’s secretary then earned a promotion by impressing her boss with copy for two accounts: Belle Jolie and the Rejuvenator. When her first champion, co-worker Freddy Rumsen, was forced to take a leave of absence because of his drinking, Peggy approached company partner Roger Sterling about getting Freddy’s office. Roger let her take it.

Outside the office, Peggy spent the night with co-worker Pete Campbell shortly before his wedding, resulting in a pregnancy. Peggy – who, like the rest of the Sterling Cooper staff, didn’t realize she was pregnant – eventually gave the baby away. Peggy also had a platonic relationship with a Catholic priest, Father Gill, who asked her to do some pro bono advertising work for the church. Peggy once bailed Don out of jail when he was being held on drunk driving charges.

Played by Vincent Kartheiser

Pete Campbell is a very interesting character that can relate to a lot of people.  It’s strange because at times he comes across as weak, other times strong, and other times still completely psychotic.  His family came from wealth having owned the majority of real estate in Manhattan — however the family fortune was lost and his family comes across and burdened by once having wealth and losing it.  He is married to a very pretty girl but he had an affair with Peggy in the beginning of the show.  His wife is really supportive and wants to have a kid but he doesn’t want to — the irony is that he had one with Peggy and doesn’t know it.

Pete Campbell is Head of Account Management at the Sterling Cooper advertising agency. A descendent of the venerable Dykeman family and a graduate of Deerfield Academy prep school, he lives with his wife Trudy in a Park Avenue apartment (financed in part by Trudy’s parents). While angling for a promotion, Pete discovered that Don Draper is living under an alias. His attempt to blackmail Don failed, so Pete got back to business by landing the Clearasil account — courtesy of his father-in-law, a top salesman at Vicks Chemical. Pete went on to lose the account when he refused to consider adopting despite Trudy’s desire to have a baby and her problems getting pregnant. More recently, Pete discovered that he already has a son — the result of his affair with co-worker Peggy Olson, who gave the baby away. Pete’s father died in the crash of an American Airlines jetliner; he has a very strained relationship with his mother.

Played by Colin Hanks

Father Gill is a visiting priest at the Catholic church which Peggy’s family attends. Upon hearing that Peggy is in advertising, the priest solicits public speaking tips to improve his delivery. Father Gill learns about Peggy’s baby when her sister, Anita, confesses that she hates her sister for seducing a man, having his child, and acting like nothing happened.

Played by Maggie Siff

Rachel Menken is the head of Menken’s, a major Jewish department store. Raised by an older sister and her hard-working father (her mother died during labor), she claims to have had a lonely childhood. She meets Don Draper while searching for an advertising agency to take her company to the next level. Shortly after she enlists Sterling Cooper’s services, she becomes a sort of advisor of all things Jewish to Don and gets romantically involved with him despite knowing he is married. Their relationship ends shortly after Don invites her to run away with him. (She refuses the offer). Her store no longer a Sterling Cooper client, Rachel runs into Don a year-plus later and introduces him to her new husband, Tilden Katz.

Played by Peyton List

Jane Sterling is Roger Sterling’s wife. A college graduate hired as Don Draper’s secretary, she quickly catches the eye of Roger, who smooths things over when office manager Joan Holloway fires her for flouting company protocol. Rehired, she begins an affair with Roger that culminates with him instigating divorce proceedings with his wife.