The Top 100 Mad Men Characters

40) Jim Hobart

Played by: H. Richard Greene

First Appearance: “Shoot” (Season 1, Episode 9)

Regardless of whether Weiner and company knew the role Jim Hobart would play back when they wrote his first appearance, as the head of McCann Erikson he provided Mad Men with a looming threat since the first season. A Faustian figure that Don and company managed to reject or escape for nearly a decade, Jim was responsible for not only the death of Sterling Cooper, but also the dissolution of its dysfunctional work family. Whether tempting the SC&P partners with accounts like Coca-Cola and Buick, or muscling Joan out after the absorption, Jim Hobart was the closest Mad Men ever came to having an outright villain, and H. Richard Greene played the part to the hilt.

39) Sylvia Rosen

Played by: Linda Cardellini

First Appearance: “The Doorway, Part 1” (Season 6, Episode 1)

Don’s mistress for Season 6, and his first (confirmed) affair in his marriage to Megan, Sylvia presented a whole host of complications that Don didn’t seem to mind. She was married to a friendly acquaintance, lived in his building, and had a heaping helping of Catholic guilt weighing on her through the relationship. Her dumping of Don was as smart as her reunion with him was stupid (he did get her son out of Vietnam). Sally walking in on the two was the wakeup call both needed, though at great cost to all parties involved.

38) Shirley

Played by: Sola Bamis

First Appearance: “Time Zones” (Season 7, Episode 1)

A fabulous dresser and frequently reassigned secretary, Shirley’s introduction in the 7^th season gave Dawn a confidante amidst the otherwise monochromatic SC&P. That she never held onto one desk for too long was more reflective of the incompetence/insecurities of her bosses (Peggy included) than her own abilities, but leaving behind SC&P after the McCann Erikson takeover made Shirley more ahead of the curve than most.

37) Julio

Played by: Jacob Guenther

First Appearance: “Time Zones” (Season 7, Episode 1)

Julio does two things really well: watch TV, and remind Peggy of her estranged son. As a comic foil, Julio made Peggy’s landlord responsibilities an amusing nightmare. But Julio’s last moment with Peggy in “Waterloo,” in which they say goodbye to one another before he moves to Newark, is a bullet aimed squarely for your heart. It’s one of Elisabeth Moss’ best scenes in the entire series, and it wouldn’t have happened without the pint-sized, popsicle-loving Julio.

36) Gene Hofstadt

Played by: Ryan Cutrona

First Appearance: “The Inheritance” (Season 2, Episode 10)

As a grandfather, Gene’s pretty great. He adores his grandchildren immensely, spoiling them with ice cream and pickelhaubes. As a father, he’s less loveable. He never liked Don, and got over the death of Betty’s mother a whole lot faster than Betty did. Repeated strokes made him a burden to Don and Betty (who he attempted to grope while in a fugue state), but the fond memories of Gene held by Sally and Bobby will likely outlive what frustrations he presented to their parents.

35) Henry Francis

Played by: Christopher Stanley

First Appearance: “My Old Kentucky Home” (Season 3, Episode 3)

If forced to choose between Betty or Nelson Rockefeller, it’s unclear which Henry would pick as the love of his life. He’s a rigid politician’s politician, but he’s a pretty decent guy all told. He takes a genuine interest in his step-kids, is involved in local government, and even knows what a feinting couch is. It wasn’t until breaking down in front of Sally last week that it was clear Henry was capable of relaying emotions other than “reassuring” and “peeved,” but he’s given Betty many of the qualities in a husband she missed out on in Don: faithful, reliable, and present.

34) Bobby Draper

Played by: Maxwell Huckabee, Aaron Hart, Jared S. Gilmore and Mason Vale Cotton

First Appearance: “Ladies Room” (Season 1, Episode 2)

One day, a tell-all titled We Were Bobbys will explain the revolving door of actors tasked with playing Don and Betty’s second, oft-ignored child. In their defense, it’s not as though Weiner and company gave any of the early Bobbys a chance to put much of a stamp on the role. Mason Vale Cotton did well holding onto the part during the later seasons though, when Bobby had a few opportunities to express himself though an appreciation of Planet of the Apes, and some poor lunchtime bartering choices.

33) Dr. Faye Miller

Played by: Cara Buono

First Appearance: “Christmas Comes But Once a Year” (Season 4, Episode 2)

Dr. Miller was one of the more successful, self-possessed, and intriguing romances Don pursued, so of course he’d break up with her after getting engaged to his secretary on a whim. Despite Allison giving her a test-case for what happens when you get involved with Don Draper, Faye kept giving him more ground, even as Don’s demands put her own career in jeopardy. Don’s dismissal of her was heartless, but at least she got to leave him with a howitzer of a diagnosis: “you only like the beginnings of things.” Well said, doc.

32) Glen Bishop

Played by: Marten Holden Weiner

First Appearance: “Ladies Room” (Season 1, Episode 2)

Characters on Mad Men don’t get much more divisive than Glen. In some eyes, he was the early poster child for the post-divorce generation the show’s cast all became a part of. To others, though, he was the weird kid from down the street whose obsession with Betty became overwhelmingly creeping. That he’s still trying to get with Betty by the time he’s 18 is even more concerning, but he proved a needed confidante to first Betty, and later Sally…which just makes him putting the moves on her mom that much more messed up, come to think of it.

31) Mona Sterling

Played by: Talia Balsam

First Appearance: “Ladies Room” (Season 1, Episode 2)

It takes confidence to play opposite an on-screen version of your husband that’s a philandering rake, but Talia Balsam and John Slattery made for a dynamite pairing as Mona and Roger. She ultimately got off better than Roger when he left her to marry Jane, as Mona at least managed to hold onto her second spouse. But it was the second act of Mona and Roger’s relationship that revealed why they ever worked in the first place, as their years of history treated them better in divorce than they did in marriage. If anyone ever truly “got” Roger Sterling, it was Mona.