Mad Men's Top 10 Secretaries

By MaryAnn Sleasman

Apr 25, 2014

"I should've bought you flowers. Out of respect!"

In honor of this week's Administrative Professionals Appreciation shenanigans, Dawn's promotion, and Shirley's amazing sass, we thought it was high time the secretarial pool at Sterling Cooper Blah Blah Blah's various incarnations got some love. While not every woman to pass through those elevator doors has been particularly skilled at her job, even those who caused bodily harm at drunken office parties have managed to delight and entertain us. 

There've been many entrances and exits to the Mad Men secretarial pool over the past seven seasons—remember when Flo worked in the switchboard room?—and this is by no means a comprehensive list of every desk jockey we've seen or heard mention around the water cooler, but here they are: the (in)famous ladies of SC&P (and SC, and SCDP), ranked for their contributions, both professionally and entertainingly. 

10. Sandy

It was difficult to choose between Lois and Sandy for the #10 spot, but Sandy won out just because her screw-up wasn't nearly as entertaining as Lois's (see below). Sandy was Lane Pryce's girl, and she mixed up two cards meant for Lane's estranged wife and Joan, inadvertently sending a racy little something something to the wrong person and causing all kinds of awkward. But hey, at least no one lost a limb. 

9. Lois

A transfer from the switchboard room, Lois eavesdropped on Sal Romano back in the day and eventually became Don's secretary. She broke the cardinal rule against crying at work (haven't we all?) and was fired for incompetence, but not before that unfortunate John Deere tractor incident

8. Hildy

Hildy! Remember Hildy? She was Pete's awesome-by-all-accounts secretary whom he enjoyed antagonizing for no apparent reason except that, well, he's Pete. She also banged Harry Crane in the office one night and they both felt really bad about it and never spoke of it again. She didn't follow the rest of the gang to Sterling Cooper Draper Pryce. 

7. Shirley

We don't know much about Shirley yet, but we've got a good feeling about her. She's office besties with Dawn (everyone confuses the two because apparently all black people look the same), she has a solid sense of humor, and she seems competent at her job. She doesn't have time for Peggy's bullshit, and she wasn't terribly torn up about being moved following the WTF flowers incident. We're looking forward to seeing more of you, Shirley. 

6. Megan

You know, Megan wasn't a bad secretary. After Ida Blankenship's death, Megan covered both reception and Don's desk—eventually leading to their romance and marriage. She was patient with Sally even before becoming a stepmom was on her radar, and prior to making the jump to fake bohemian/sometimes actress, Megan made the jump from secretary to sometimes copywriter, mirroring Peggy's rise before her. 

5. Peggy

As a secretary, Peggy was skilled enough and took all of the political movement at Sterling Cooper in stride; she was trained by Joan, after all. Way back before she struck copywriting gold with a basket of kisses, Peggy rocked the frumpy-sweaters-and-ponytail look, banged Pete, and had his bastard child before they pulled a Don-and-Megan and lived happily-ish ev— wait, no they didn't. She gave the kid up and he married Trudy, but it all worked out for the best, right? Right? 

4. Allison

Poor Allison. She was probably the best secretary Don ever had. Really! Unfortunately, when Don started sending her on more personal errands and eventually did the horizontal tango with her in his sad, liquor-soaked bachelor pad, she thought it actually meant something. She was fired after lobbing a cigarette lighter at Don's head—something so many girls before her only dreamed of doing. 

3. Ida Blakenship

Despite being a "hellcat" in her youth, the elderly Miss Blankenship was assigned to Don following the Allison Incident, specifically to discourage him from attempting to sleep with her. Sure, she was a terrible secretary—but she was also a downright entertaining one, taking great delight in announcing when Don was preoccupied on the porcelain throne. Roger Sterling slept with her in their younger days, and he called her "the Queen of Perversion" in his memoirs. When she died at her desk, Bert Cooper compared her to an astronaut.

2. Dawn

Sterling Cooper Draper Pryce hired Dawn, the firm's first African-American employee, mostly by accident—she responded to the tongue-in-cheek "equal opportunity" job posting SCDP ran to stick it to a rival agency, and the partners basically had no choice but to add some diversity to the payroll. Regardless, Dawn awesome. Despite her co-workers' almost-daily casual racism, Dawn is dedicated to her job, though justifiably frustrated by its limitations. Just last week, she was promoted to Joan's old job as Head of Personnel, a.k.a. Office Overlord, and I'm so excited for her. SO EXCITED.

1. Joan

Joan has done it all. Joan has seen it all. Joan has been with the boys at SC&P for 16 years, according to her own calculations, and while she's finally earned herself a partnership and landed a swanky upstairs office, Joan has long been responsible for pulled all the strings and making the day-to-day operations at SC&P and its similarly named predecessors run smoothly. While her personal and private lives are hopelessly tangled, you'd never know it to interact with Joan, who's reduced the science of steely professionalism down to a high-concentration formula. You won't find Joan crying in a restroom, even though a lot of the time, she has plenty of reasons to.  

Who's your favorite Mad Men secretary?

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  • violetcobra Apr 15, 2015

    Joan. Just Joan. WWJD? I love her girl on top perseverence!

  • dh4645 Apr 29, 2014

    Hildy is the best

  • ben45tpy Apr 27, 2014

    Fantastic list, they're all great.

  • Carolee99 Apr 26, 2014

    Joan is one of the most awesome characters on TV ever. Her sense of style is fabulous and she really knows her stuff. I'm glad that she is finally getting the credit that she deserves.

  • MarlboroMagpi Apr 25, 2014

    Joan is definitely the best and the most successful too ! I probably hate her in real life :-)

  • Onenote111 Apr 25, 2014

    I have every season on blue ray. I have dreams about Mad Men. I'm heading down the rabbit hole , and I love it.

  • mrjimmyjames Apr 25, 2014

    Lois was hilarious. Blankenship should be ranked higher. Her death episode was really well handled as well.

  • Sbriseno07 Apr 25, 2014

    How can you forget Meredith! She is so dumb, but so entertaining. Like when she let in the guy who served Joan and she had a plane thrown at her. She should take Sandy's spot.

  • valeriel Apr 25, 2014

    Joanie! Great, great list!

  • ToddMurray Apr 25, 2014

    Nice list, Maryann! I've always been partial to Peggy, despite her batshit crazy behavior this season, with Joan a close 2nd.

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