Donald Trump and the Mad Men World of Sexual Harassment

vintage cartoon sexist office secretary

Trump is the worst kind of throwback to the Mad Men era when misogyny in the workplace was laughed off as business as usual. The caption for this vintage Playboy Magazine cartoon reads: “And I was so afraid that working for a giant corporation would be an impersonal, cold, inhuman relationship.”

Take My Secretary, Please!

Is anyone surprised that when it comes to women, Donald Trump and Don Draper have a lot in common? When it comes to creepy, retro sexism, The Donald trumps even Don Draper.

Detailing Trump’s history of troubled behavior with women in a lengthy article, The NY Times just spent weeks interviewing more than 50 people to get a sense of Donald Trumps private behavior with women over more than 40 years.

Trump is the worst kind of throwback to the Mad Men era when misogyny was laughed off as business as usual.  The suggestive remarks and creepiness of male workers made sexual harassment a near daily ordeal faced by women in the workplace.

Sexism and sexual harassment at the office was sometimes invisible because it was so darn normal.

In fact it was the stuff of great humor.

The world of sexist jobs, businessmen men objectifying and infantilizing women, lascivious philandering and wild office parties was fodder for comics and cartoonists alike.

Misogyny was easily laughed off as office antics.

Not a one of these cartoons would pass HR today.

Vintage Sexist Office Cartoons

vintage Playboy cartoon sexist office

“Take an indecent proposal!” Vintage Playboy cartoon 1966 by Interlandi


Playboy cartoon computers sexist 1969

“I’m programing you as a pushover- I hope you won’t let me and the company down!” Playboy cartoon 1969


Playboy cartoon office sexism 1970s

“My wife is gone. You may come out, Miss Honeycutt.” Playboy cartoon 1971 by Booth



sexist office cartoon Playboy

Bosses Portrait Vintage 1966 Playboy cartoon by Interlandi


penthouse Cartoon office sexist

“Heavens, is it Valentines Day already?” Penthouse Magazine 1980


vintage sexist office cartoon

A take on IBM’s classic slogan, advising the boss to think as he chases her around the desk. Vintage cartoon Esquire

Many of these cartoons were never meant to be glimpsed by the girls, appearing in male magazines like Playboy and Esquire, to be read at men’s clubs or the Barber shop where an earlier generation ogled the Police Gazette.

vintage sexist cartoon

“You certainly have a one track mind, Mr. Bree!” Vintage Playboy cartoon 1962


vintage sexist office cartoon

“Guess what Mom. I’m Miss Magic Lift of 1958!” Vintage Playboy cartoon 1958


vintage playboy cartoon office seist

“No kidding, Miss Harmon. I think the firm is very lucky to have someone as thorough as you in the typing pool.” Playboy cartoon 1978


Playboy cartoon office sexism

Playboy cartoon 1965

Christmas Parties

vintage sexist office cartoon

“Looks as though the Entertainment Committee has come up with some fresh ideas for this years Xmas party!” Vintage Playboy cartoon 1967 by R. Taylor


vintage sexist cartoon office

“Last year we gave him an electric shaver.” Vintage Playboy cartoon


vintage cartoon sexist office

“Miss Beverly, I want an option on you for the Christmas party.” Vintage Playboy cartoon


vintage sexist cartoon office

The fear that computers would end up replacing office antics would be proven wrong. Vintage Playboy cartoon 1962


playboy cartoon office party sexist

“Jenkins, have you ever wondered why your promotions in this company haven’t kept pace with everyone else’s?” Playboy cartoon 1976 by John Dempsey


Mad Men may have offered us a front row seat to the world of mid-century misogyny, but Donald Trumps remarks and behavior  has hopefully  opened the dialogue to recognizing that sexism still exists today.

And it is no joke.

You Might Also Enjoy

Trump All the Publicity That’s Fit to Print

Trump and the Tabloids

© Sally Edelstein and Envisioning The American Dream, 2016. Unauthorized use and/or duplication of this material without express and written permission from this blog’s author and/or owner is strictly prohibited. Excerpts and links may be used, provided that full and clear credit is given to Sally Edelstein and Envisioning The American Dream with appropriate and specific direction to the original content.



  1. I will (foolishly? honestly?) expose something of myself with this comment Sally. No, not that; calm down. (laughing)

    As I read through this post and the vintage images, I thought “I’ve seen Sally’s images here before. An earlier post maybe?” I continued reading… “Now I have DEFINITELY seen those images before!” Then it hit me… I remember some of these cartoons as a teenager from my Dad’s lifetime subscription to Playboy. Hah! Please allow me to briefly say, however, that I did not grow up or was raised in a traditional (puritan?) Conservative home. Dad was agnostic and a Freethinker; Mom simply loved him like a good 1950’s – 1970’s wife was suppose to back then. Dad was not a typical Sexist back then either — he stood up for equality all the time. He and Mom were however, more open about sexuality than the typical Texas families. To my the/my point…

    Having grown up with “unconventional” social views — a positive in this nation compared to other countries — Donald (t)Rump is absolutely the quintessential 1960’s Sexist. Give him enough time and enough circumstances around or with women and he proves it 97 times out of 100. It doesn’t take too much ‘probing’ to find his Sexist wiring. The primary reasons why Melanija Knavs is still remarkably married to (t)Rump — and this is not in any way meant to sound sexist — is… 1) she’s from a Slovenian-Yugoslavian culture yet finds American culture much more “equal” than her native land; a “speak-when-spoken-to” Slovene female? She may be innocently ignorant of Donald’s true character. And 2) money, money, and MORE money ad infinitum… which often hides or blinds someone from reality and the core nature of someone or a spouse. Though I do not know Melania personally, she has never struck me as a iconoclast sort of woman. Correct me if I’m wrong. I see that public image conflicting disastorously with Donald’s throne. 🙂

    Aside from (t)Rump’s track-record with marriages and women, the United States will need to be completely prepared for hyper-volatile events should another nation’s leaders or Prime Ministers, etc, are female! THAT is what stresses me out endlessly! 😮 😦

    Great post Sally! ❤

    Liked by 1 person

    • I agree, the very thought of Trump dealing with international women in positions of power is very concerning. Since he sites his experience with running the Miss Universe Contest as his foreign policy credentials, we all have a lot to be worried about.
      BTW, though you may recall some of these cartoons from your childhood, I have used a few of them in a previous post

      Liked by 1 person

      • Well said Sally. I don’t understand why so many Americans (a majority of Republicans?) STILL believe the U.S. is an island/continent to itself and can be (foolishly) influenced by or dictate upon or impervious to global events, social movements, economies, and foreign crisis’! We haven’t been that ‘Independent’ 1912 – 1940’s nation since Dec. 7, 1941! We have been fully vested in world events and foreign cultures for at least a full century! Our Commander in Chief must be fully capable of managing WORLD affairs in a plethora of ways and wisdoms! Period!

        Simply put Donald (t)Rump has the least capable stoic, foreign dignitary prowess of all present candidates, maybe the least since 1776. And since the beginning of Women’s Sufferage, more and more powerful, highly capable (needed) women are firmly inside national and world politics! It will only increase in 4-8 years! Sadly, (t)Rump is way behind the times. :/

        Liked by 1 person

  2. And yet, so many of us would like to see Trump as President. I find it real interesting, and angering, Trump attacking Bill Clinton for womanizing, then blaming the victim Hillary.

    Liked by 2 people

  3. Pingback: Making America White Male Again | Envisioning The American Dream

  4. Pingback: Sexism, So What’s New? | Envisioning The American Dream

  5. Pingback: This Election Day Don’t Be a Sucker | Envisioning The American Dream

  6. Pingback: Trump’s Dreaming of a White Male Cabinet | Envisioning The American Dream

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s

%d bloggers like this: