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Ranking All Of Don Draper’s Sexual Conquests On The Crazy-Sexy Scale

By / 09.20.12
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I got to thinking about Mad Men again this week after seeing a suave, mustachioed Jon Hamm "direct" a video for Aimee Mann, and for whatever reason (I'M A MAN), I began recounting all of his lovers through five seasons of Mad Men, what with him likely heading back into another philandering phase.

Specifically, it occurred to me that Don was often attracted to a particular kind of lady: The crazy kind. He's had a couple of stable relationships with sane women, but for the most part, Don likes the wackjobs: The free spirits, the idealists, the kinky, rough ladies. He's got a thing for powerful, controlling women, but once he enters a relationship with them, he no longer likes to be controlled. I think there's something in Don Draper's DNA about wanting to dominate, but he's also drawn to the challenge of finding the most difficult women to dominate.

To be honest, he's not very right in the head. So, to help fill the Mad Men void for another six months, I took it upon myself to do a very cursory ranking of Don's sexual conquests on the crazy-sexy scale, combining the characters' 1-10 crazy scores with their 1-10 scores on pure sexual appeal (irrespective of actual hotness).

12. Rachel Menken (Maggie Siff)

A department store head with a good head on her shoulders and great chemistry with Don, Rachel ultimately shuts down Don's fantasies to run away with her after realizing it's not her that he wants to run away with, it's anyone. Along with Faye Miller, she may be the most sane of all of Don's lovers, and thus one of the less interesting.

Crazy: 1
Sexy: 5
Total: 6

11. Bethany Van Nuys (Anna Camp)

A set up from Jane Sterling basically as a diversion for Don post-divorce, Bethany is very pretty, very dumb, and very boring. I'm sure she's got some crazy in there, but she's not smart enough to uncover it.

Crazy: 2
Sexy: 5
Total: 7

10. Dr. Faye Miller (Cara Buono)

An independent modern woman who helps to persuade Don to send the letter about the tobacco industry, and who carries on a secret affair with Don, which he breaks off once he realizes that "modern" also means "bad with kids." Don's relationship with Faye was one of his healthiest relationships, which of course means that it was doomed from the beginning.

Crazy: 1
Sexy: 7
Total: 8

9. Suzanne Farrell (Abigail Spencer)

Another of Don's hippie idealist lovers (this one with a brother with epilepsy), Suzanne was also Sally's third-grade homeroom teacher, and it takes a fair amount of crazy to sleep with one of your student's fathers. But then again, the handicapped brother also grounded Suzanne.

Crazy: 3
Sexy: 6
Total: 9

8. Joy (Laura Ramsey)

Young, carefree hedonistic California girl who Don uses as an escape while he's out on a business trip. She was as much into having fun as Don; she was only interested in great sex.

Crazy: 2
Sexy: 8
Total: 10

7. Allison (Alexa Allemani)

Don's secretary with whom he had an impulsive drunken affair after a Christmas party and tried to blow it off, much to the chagrin of Allison, who would eventually burst into tears during a focus group and walk out. On the one hand, getting upset after your boss sleeps with you and then blows you off is a sane reaction; but on the other hand, a focus group is maybe not the best place to have a nervous breakdown.

Crazy: 6
Sexy: 4
Total: 10

6. Shelly (Sunny Mabrey)

Just a stewardess, whose sexual dalliance with Don is interrupted by a fire drill. No crazy there, but she was super hot, and I like to think that Don and Shelly finally made it happen 30,000 feet up in the air.

Crazy: 1
Sexy: 9
Total: 10

5. Prostitute Who Slaps Don

She was a prostitute who slapped and degraded Don, but then again, she's about the only woman who could control Don. She was sure of herself, and despite the fact that she had sex for money, she was a sure sight more sane than most of Don's lovers.

Crazy: 3
Sexy: 9
Total: 12

4. Betty Draper (January Jones)

Don's first wife, Betty is sh*tbird crazy, moody, manic-depressive, lashes out at her children and her husbands, and mostly sulks when she's not eating. Also, seems particularly dull in the sack. There's basically nothing about Betty that is attractive except for her crazy, but in the sexual sense, that crazy never really translated.

Crazy: 10
Sexy: 3
Total: 13

3. Midge Daniels (Rosemarie Dewitt)

A hippie beatnik pot-smoker with a lot of lovers (season one) turned painter/heroin addict (season four) who was all too willing to sleep with Don for a little money for her fix. It doesn't hurt that I have a monster crush on Rosemarie Dewitt.

Crazy: 6
Sexy: 8
Total: 14

2. Megan Calvet/Draper (Jessica Pare)

Don's second wife, a secretary turned copy writer turned wannabe actress who wants to be her own woman and refuses to be Don's housewife, though she is often quick to forgive if she's shown a little affection. She's had her bouts of crazy, but she's also one of the few women on the show who recognizes her situation and attempts to better it. She's also off-the-scales sexy.

Crazy: 5
Sexy: 10
Total: 15

1. Bobbie Barrett (Melinda McGraw)

An older woman (for Don) and the wife of an insult comic, Bobbie is basically violated by Don in the bathroom during a dinner with their spouses, which leads to an affair of passionate hate f**king, which Bobbie is all too happy to continue. She loves the attention, she loves the abusive nature of the relationship, and she loves that she can also screw over her husband. She basically gives Don the same thing the prostitute gives him, but she's not paid for it.

Crazy: 8
Sexy: 7
Total: 15

Begin Slide Show ›
TOPICSMad Men
TAGSDON DRAPERJON HAMM

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