50. Bobby Draper (Don and Betty’s son)
Screw you, Bobby.
49. Dick Whitman (Young Don Draper before he was Don Draper)
Is there anything more disappointing than Don’s flashbacks to his childhood self? Nothing kills that mysterious aura like seeing him mope around like a mid-puberty Moe from The Three Stooges.
48. Joey Baird (Sterling Cooper, artist)
Just a hateful character with no depth or redeeming qualities – Mad Men at its worst.
47. Greg Harris (Joan’s fiancée)
Speaking of hateful, Greg Harris was just a really boring character until he raped Joan, in an ill-advised storyline that went over about as well as it sounds like it would.
46. Gene Hofstadt (Betty’s dad)
Hated Don, fondled Betty. I think it’s safe to say nobody misses Gene.
45. Glen Bishop (Betty’s friend)
Have you ever wondered why, exactly, Glen Bishop existed in the Mad Men universe? What was the point of this marginal character who somehow kept turning up again and again? Well, he’s played by Marten Weiner, the son of showrunner Matthew Weiner. So, there you go. Glen is odd, and not in an intriguing or enjoyable way, and his storyline with Betty was more absurd than anything.
44. Gail Holloway (Joan’s mom)
About twice a season Gail shows up to say something that annoys both Joan and viewers, before disappearing into the background with Kevin again.
43. Abe Drexler (Peggy’s boyfriend)
Mad Men usually mocks the political right and left with equal glee, but Abe was a particularly disdainful sendup of the bleeding-heart liberal. He was mostly grating, and then Peggy stabbed him.
42. Gene Draper (Don and Betty’s son)
Gene makes for a slight improvement over the above-listed characters because he’s essentially an inanimate object, like a doorknob or a chair. He’s a neutral baseline in the rankings – everyone already ranked detracts something from the show, and everyone coming up adds (at least a little) value to the proceedings.
41. Meredith (Sterling Cooper, secretary)
Mad Men’s depiction of Meredith, the office bimbo, always felt a little sexist. And not intentional-sexism-as-critique, either.
40. Jane Sterling (Roger’s second wife)
Mostly just an excuse for Roger’s life to spin even further out of control between heart attacks and LSD trips.
39. Margaret Sterling (Roger’s daughter)
Definitely ranked a little higher after she finally did something interesting and ditched her family to join a commune.
38. Father Gill (Peggy’s priest)
Father Gill, a Jesuit priest played by Colin Hanks, wins my award for Most Inexplicable Character. He seemed like he wandered in from a different show.
37. Paul Kinsey (Sterling Cooper, copywriter)
It was pretty funny when he became a Hare Krishna and started writing Star Trek fanfiction.
36. Trudy Campbell (Pete’s wife)
It’s a shame because I love Alison Brie so much in Community, but Trudy was generally a shrill and thankless role.
35. Rachel Menken (Draper mistress)
The first in a series of failed romantic flings for Don. Her ranking is lowered by the seemingly endless assembly line of disappointed brunettes that followed her.
34. Anna Draper (The real Don Draper’s widow)
I feel like we should’ve gotten more out of Anna, mostly because Don (as in, Dick Whitman posing as Don) loved her so much. Unfortunately, she never meant as much to us as she meant to him.
33. Francine Hanson (Betty’s friend)
Francine was funny and seemed to have a lot of personality, largely in part because she always shared screen time with the perpetually repressed Betty.
32. Conrad Hilton (Sterling Cooper client)
Like Don, I found Hilton’s cryptic remarks and crazy demands alternately fascinating and exasperating.
31. Megan Calvet (Don’s second wife)
Nothing made me appreciate Betty like Megan.