30. Michael Ginsberg (Sterling Cooper, copywriter)

What to make of Ginsberg? Someone so weird should’ve been more entertaining, but I guess that made him realistic – like the real-life creepy guy at your office, he was more awkward than fun. Then he had a nervous breakdown and cut his nipple off…

29. Caroline (Sterling Cooper, secretary)

I always got a kick out of Roger’s beleaguered secretary.

28. Lou Avery (Sterling Cooper, creative director)

I also got a kick out of Lou Avery. But, he is a humongous tool, so your mileage may vary.

27. Henry Francis (Betty’s second husband)

I liked that Weiner never resorted to making Henry a generic villain, someone for the audience to blindly hate because he replaced Don for Betty and the kids. Henry has flaws, but he’s actually one of the show’s more respectable and upstanding characters.

26. Marie Calvet (Megan’s mom)

As you can see, I actually like Marie a lot more than I like Megan. She’s so sassy and French and says things like, “Not every little girl gets to do what she wants – the world cannot support that many ballerinas.”

25. Faye Miller (Draper mistress)

One of Don’s more memorable flings, I actually thought Faye might finally be the one who could whip Don into shape.

24. Sylvia/Arnold Rosen (Draper mistress, her husband)

I liked the Rosens – Arnold was genuine and amusing, and Linda Cardellini was great in her run as the anguished Sylvia.

23. Burt Peterson (Sterling Cooper, account executive)

Burt’s appearances on the show consist almost entirely of him being fired, and it’s amazing.

22. Shirley (Sterling Cooper, secretary)

Shirley keeps it 100.

21. Stan Rizzo (Sterling Cooper, art director)

At first I detested Stan and his annoying alpha male act, but I’ve grown to like him. His relationship with Peggy, in particular, has become more and more interesting over the years.

20. Mona Sterling (Roger’s first wife)

Mona is secretly hilarious – she can parry wits with Roger, which is no short order. And they’re married in real life!

19. Harry Crane (Sterling Cooper, media head)

It was always hard to take Harry Crane seriously because Mad Men never took Harry Crane seriously. It’s fun having a character to kick around, but it’s kind of sad he didn’t develop more considering all the screen time he got.

18. Bert Cooper (Sterling Cooper, senior partner)

Am I alone in enjoying Bert Cooper in death far more than I ever enjoyed him in life? He was the least interesting partner, but his postmortem song-and-dance routine to “The Best Things in Life are Free” was one of my all-time favorite Mad Men moments.

17. Ted Chaough (Draper rival, Sterling Cooper partner)

Ted Chaough is like ginger ale: it’s not what you ordered, but you’re not gonna send it back, either.

16. Jim Cutler (CGC partner, Sterling Cooper partner)

I always wanted more Jim Cutler. His perpetual dismay over the organized chaos that is Sterling Cooper was hysterical, as was the way his highbrow sophistication got repeatedly revealed as a flimsy disguise for his own brand of pathetic childishness.

15. Ida Blankenship (Sterling Cooper, secretary)

For a while there, it seemed like Mad Men secretaries were just excuses for proto-sexual harassment incidents. Then Blankenship bumbled onto the scene, screwed up every message, treated Don with a mixture of apathy and contempt, and died at her desk. Probably the broadest comedy the show ever attempted, I think a lot of people hated her, but I thought she was incredible.

14. Bob Benson (Sterling Cooper, employee)

A fascinating enigma – I was intrigued when Bob was onscreen because I was trying to figure out what the hell his deal was. Plus the whole “Bob Benson inadvertently kills Pete’s mom” storyline was amazing.

13. Dawn Chambers (Sterling Cooper, secretary)

I’m a huge fan of Dawn. She was a part of some of the show’s most heartbreaking moments, and her endearing nature gave viewers someone to root for in the show’s generally misanthropic world.

12. Ken Cosgrove (Sterling Cooper, account executive)

Ken used to be pretty bland on the surface, but with a lot of fascinating things happening underneath (like his literary ambitions, for example). Then he got shot in the face and started wearing an eye patch! Now I love everything about Kenny.

11. Duck Phillips (Sterling Cooper, director of account services)

I have a distinct feeling that I’m the only person that liked Duck. Hell, I’m not even sure why I liked him. I guess it’s because he was a worthy rival for Don (he even beat him in a fistfight!), at least for a little while, and because his status as a seemingly normal person served to highlight the absurdity of all the other characters at Sterling Cooper. Then things got weird, and he tried to take a dump on Don’s chair. All around, I really enjoyed the Duck run.