
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



I think Betty may have been bonkers in bed at one time. The scene she and Don had in Italy leads me to believe that at one time the Drapers were very sexually compatible. Who knows how much fun Betty was when they were first together? They seem to enjoy each other in the slides shown during the carousel presentation. We only meet Betty after years of being with Don have probably destroyed her. I’m totally with you on the Rosemarie DeWitt, though.
Another vote here for Rosemarie DeWitt.
Granted, Betty got fat last season, but can you honestly say January Jones is only a 3 on the sexy scale?
Its like he TOTALLY forgot Betty in Italy aka The Better Days
I think he’s also adding in personality to “sexy”. Betty is such a buzzkill and so straight-laced that while she’s physically attractive, her personality is very non-sexual.
Beautiful doesn’t mean sexy. You kids today with your good eyes and unwillingness to have outstanding sex with someone who isn’t that pretty.
I’d say she’s a 3. To be skinny and crazy=hot, to be fat and crazy=Divorce
Hi, welcome to blogging. People post their opinions and we read them and comment.
Looks like Chipper should have retired a few years ago.
This is the worst idea for a discussion ever!
And now let me spend a long paragraph taking part in it!
I forgot about Joy. Joy’s sexy >*
What you’re trying to say is … more corgis?
And then we make fun of other people’s comments, natch.
You think that adding crazy and sexy together is the correct way to do that equation?
Should have multiplied.
Don’t forget Bethany Van Nuys gave Don a beejer (it might have been a hj, I can’t remember) in the cab after one of their dates. I think that warrants a +1 on both the crazy and sexy scales.
It was a BJ. Based on the time period and its mores, I think both the crazy and the sexy have to be multiplied by 2.5. She may actually be in her own category.
You obviously don’t know Dustin, pretty sure he would make 10 lists a day if he could. Then make a list of the lists.
No way Bobbie Barrett is more crazy than Joy or Suzanne. Bobbie used sex to get what she wants. Suzanne knew better, had prior bad experiences and still went with Don. If doing the same thing time and time again, expecting a different result is the definition of insanity, then Suzanne should be considered the most crazy.
Whoa, this post got all insightful.
BOOBZ.
Insightful? Seriously?
“If these type of pointless ranking posts are going to have nothing but your own opinion, what exactly is the point of sharing these with us?”
How dare you not use a scientific formula to determine a subjective topic!
Chipper Bones 10 Worst Comments
Does anybody else get a “smart Nancy Sinatra” vibe off Dr. Faye? She has that sneaky kind of hotness.
Yup. I loved me some Dr Faye. I knew it wasn’t going to work with her and Don, but she would be my personal #1.
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.
Silly Dustin, all women have sex for money (if not a straight up cash transaction, for other types of consideration), which means that all women are at least a little crazy. A sentiment I totally co-sign.
I was so happy to see Midge return in season 5, but was legitimately depressed to see what had happened to her.
And Rachel Mencken may have been perfectly sane, but I still wish she’d answer my letters…
Don should retire from the AD Department and start an acting career. My opinion!
no way Allison is crazier than Joy. I mean Joy was a hedonist that was traveling around with her father
Did Danger object to these rankings because you didn’t include Cool on the Scale?
Am I the only one surprised the number is as low as twelve?
I got more of a crazy vibe from the teacher than you did apparently.
The teacher definitely had a screw or two loose. Also a bit of a savior complex.
Damn in sorry I missed getting in on this one. I’ll say it again though: Betty is only crazy because Don made her that way. He was the one who couldn’t get it up when she was wearing lingerie in valentines day. Don is turned on by doin the wrong thing. He was born to a prostitute and that clearly works in to how he conducts his sexual relationships.
“He was born to a prostitute and that clearly works in to how he conducts his sexual relationships.”
I understand why you would like to think this but the Don Draper character’s attitude is consistent with the stereotype of how powerful men treat women, especially those outside of the man’s social class and with less power/money. It’s a common tv trope and probably somewhat realistic.
“What an idiotic list…and you ranked it incorrectly!”
FFS.
Swing and a miss, Chip.
*sad walk back to dugout*
I would just like to point out that these crazy ladies ain’t got nothin’ on Louis CK’s.
When they introduced the ‘crazy/hot scale’ on How I Met Your Mother, Abigail Spencer played that crazy/hot girlfriend of Ted’s. I feel she should’ve gotten some bonus points.
There’s not really a pantheon of idiotic list posts, is there?
Do you really come here just for the news? Are you really that excited about NBC’s mid-season schedule announcement?
That list couldn’t be any more incorrect….
Melinda McGraw. Nice choice for number one. In the Quantum Leap episode where Charles Rocket is “Scrooge” Melinda McGraw played the Salvation Army lady. Always sexy.
After hearing Rachel’s speech on Zionism and Israel (especially about it “having” to “be,” regardless of what it did to the indigenous people of the land) I’d have to bump up the “crazy score” to at least five.
Good choice for number 1.Bobbie and Don was the hottest,sexiest hook up on the show.I cant believe you didnt mention him tying her down on the bed and leaving her there! I loved that they were so similar that they basically took out their self loathing on each other. Good stuff!