30) Lou Avery
Played by: Allan Havey
First Appearance: “In Care Of” (Season 6, Episode 12)
It was bold of Mad Men to include a historical figure like Lou Avery in the show, as Scout’s Honor remains one of today’s most beloved cartoon creations. Like all great artists, though, Lou Avery wasn’t really cut out for the corporate world. As Don’s replacement, and source of Peggy’s frustration, Lou was as smug as he was out of touch. He was better at accidentally overhearing his subordinates shit-talking him than he ever was as a creative director, and his casual sexism was regressive even by SC&P’s standards. And that tiki bar in his office? Tack. Y.
29) Herman ‘Duck’ Phillips
Played by: Mark Moses
First Appearance: “Nixon vs. Kennedy” (Season 1, Episode 12)
A callous excuse-maker when sober, and a blathering disaster when drunk, Duck is a 10th dan black belt in the art of self-sabotage. He’s got the cunning to set himself up as president of Sterling Cooper following the PPL merger, but can’t keep his mouth shut long enough to close the deal. His downward spiral afterwards was marked by one pathetic low after another (though, trying to take a crap in Roger’s office was a series comic high), and it’s only once he got back on the wagon that a functional human being to reemerge. But Duck did once abandon his Irish Setter just so he wouldn’t feel guilty about falling off to begin with. Go ahead and ruin your own life, Duck, but leave Chauncey out of it!
28) Midge Daniels
Played by: Rosemarie DeWitt
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
How memorable Midge is as a character versus how memorable she is as a character played by Rosemarie DeWitt is debatable, but as the first of Don’s sidepieces we’re introduced to, Midge set a pretty high bar. Bohemian, intelligent, and better at resisting Don’s allue than most, our sad final reunion with Midge – technically married to a penniless addict – does little to overshadow what a unique presence she was on Mad Men during its first season.
27) Miss Ida Blankenship
Played by: Randee Heller
First Appearance: “The Rejected” (Season 4, Episode 4)
“”She was born in 1898 in a barn. She died on the 37th floor of a skyscraper. She’s an astronaut.” No one can top Bert Cooper’s succinct, poetic summation of one of Sterling Cooper’s oldest employees (though, Roger tries with “Queen of Perversions”), but Miss Blankenship’s tenure on Mad Men was as brief as it was hilarious. She even managed to die in a manner that made her a hall-of-fame-worthy secretary. You’ve been long gone, Miss Blankenship, but never forgotten.
26) Freddy Rumsen
Played by: Joel Murray
First Appearance: “Babylon” (Season 1, Episode 6)
One of the few alcoholics at Sterling Cooper lucky enough bounce back from his bottom, Freddy became a lot less fun, but a lot healthier the minute he stopped drinking. Booze cost him his job at the agency, and with him went one of Peggy’s first real supporters. His freelance pop-ins have been welcome ever since, whether bailing Don out of a drunken stupor, or proving that the power of Don’s pitches are in his words, not his looks. He even helped Peggy get her job as copy chief at CGC, another opportunity opened up to her by Freddy’s aid/mistakes. No Freddy peeing himself before the Samsonite meeting, no Peggy on Samsonite. No Peggy on Samsonite, no “The Suitcase.” Thanks for taking one for the team, Freddy.
25) Meredith
Played by: Stephanie Drake
First Appearance: “A Little Kiss, Part 2” (Season 5, Episode 1)
In three seasons Meredith went from receptionist, to secretary, to invaluable supporting presence, assuming you consider perky and oblivious commentary a valuable contribution to Mad Men. Whether putting the moves on Don during a pep talk, sitting on the receiving end of Joan’s fury, or just generally being a brightly-dressed ray of sunshine, Meredith seemed to live in her own little world. By the time she’s cheerily telling a furious Jim Hobart he’ll have to leave a message, Meredith is already a given for the Mad Men comic relief pantheon.
24) Paul Kinsey
Played by: Michael Gladis
First Appearance: “Smoke Gets in Your Eyes” (Season 1, Episode 1)
A bon vivant, Princeton alum, a cappella singer, supporter of the proletariat, and author of the worst Star Trek spec script ever written, the accumulated respect Paul Kinsey garnered at Sterling Cooper probably wouldn’t measure up half as high as his own opinion of himself. Supportive of others until they make him look bad, progressive so long as everyone else knows about it, and constantly in danger of running his mouth, Kinsey was an easy cut from the staff when Sterling Cooper needed to reinvent itself. The funny thing is, Kinsey would have been a perfect fit for the looser direction SCDP would take, but the show had used Kinsey for all he was worth by that point.
23) Marie Calvet
Played by: Julia Ormond
First Appearance: “At the Codfish Ball” (Season 5, Episode 7)
Frequently exasperated mother of Megan, occasional lover of Roger, and constant source of en francais smack talk, Marie is a treat to watch in action. She seems to get off on belittling her husband, and leaves no wound in the lives of her daughters unsalted. But she’s also a vivacious boozehound with a withering sense of humor, and maybe the only woman who could go toe-to-toe and bon mot-for-bon mot with Roger. Here’s hoping those two crazy kids can make it work!
22) Dawn Chambers
Played by: Teyonah Parris
First Appearance: “Tea Leaves” (Season 5, Episode 3)
Like Peggy before her, Dawn was able to turn an inch of an opening at a white, male-dominated office into a mile of a career. Though initially hired as part of an equal opportunity stunt meant to embarrass SCDP’s competitors, Dawn quickly worked her way up to office manager, earning the respect of Don and Joan in the process. Granted, like Peggy, her personal life became almost non-existent thanks to the demands of the job, and as with Hollis, Dawn’s status as the only African American employee in the office put her in a precarious position during the later years of the civil rights movement. Sometimes that would lead to cringe-worthy bits like an awkward sympathy hug from Joan, or really telling ones, like an invite to stay at Peggy’s house that revealed more about Miss Olson than she’d like. The life of a pioneer isn’t easy, but Dawn’s perseverance and determination always gave you someone worth rooting for.
21) Jim Cutler
Played by: Harry Hamlin
First Appearance: “The Flood” (Season 6, Episode 5)
Sterling Cooper has rarely been without a troublemaker amidst its ranks, but few were as devious and clever as Jim Cutler. Witty as Roger but nowhere near as vain, and with a mind for business that outpaced Pete or Don, Cutler masterfully insinuated himself into the driver’s seat at SC&P, managing to turn Joan and Bert against Don. Harry Hamlin made Cutler a guy you loved to hate – plus his access to a Dr. Feelgood made him someone you wanted to party with too. And unlike other schemers, Cutler managed to exit the agency in a gold parachute, not disgrace.