60) Lois Sadler
Played by: Crista Flanagan
First Appearance: “The Hobo Code” (Season 1, Episode 8)
Lois didn’t leave a huge mark on the show for most of her run. She had a thing for Sal, and used to be a switchboard operator. Then she ran over a guy’s foot with a lawnmower. Immortalization in television history: achieved.
59) Danny Siegel
Played by: Danny Strong
First Appearance: “Waldorf Stories” (Season 4, Episode 6)
The cure for the common employee, Danny’s hiring at SCDP owed entirely to a drunken mistake by Don, and a blood-tie to Jane, and not his impressive portfolio of other people’s work. Danny’s contribution to the office from thereon out was minor, but he found a better life for himself out in California after the agency let him go. Plus, he eventually got to punch Roger in the junk as revenge for all the jokes about his height, which was a great time for all (except Roger).
58) Abe Drexler
Played by: Charlie Hofheimer
First Appearance: “The Rejected” (Season 4, Episode 4)
Re-watching the early Abe and Peggy episodes can be a little tough; after all, how does a relationship that starts so promising turn into one where Peggy stabs Abe with a homemade bayonet, and he breaks up with her by calling her “the enemy?” Abe embodied the counter-culture movement that Peggy was only ever a tourist in, so they were pretty much doomed from the jump. That Peggy got a few good pitch ideas, and a whole apartment out of her time with Abe means we can forgive some of his trespasses, and questionable facial hair choices.
57) Margaret Sterling Hargrove
Played by: Elizabeth Rice
First Appearance: “Babylon” (Season 1, Episode 6)
Look, we all love Roger. But we can all agree that, as far as paternal figures go, he’s about the only guy out there that could make Don look like father of the year. So you can blame nurture for Margaret’s obnoxious attitude, which includes a fondness for dullards (sorry, Brooks), making the Kennedy assassination all about her (okay, it was her wedding day), and a general entitlement complex. Like Roger, we’re fine with abandoning her to the life of a barnyard hippie.
56) Greg Harris
Played by: Sam Page
First Appearance: “For Those Who Think Young” (Season 4, Episode 1)
Really, you could get across everyone’s feelings about Greg using audio clips of a dry-heaving house cat, but his importance to Joan’s growth through the series can’t be ignored, even in light of the fact that he’s a worthless, delusion piece of human garbage. Were not so many indelible Joan moments tied to Greg – such as the reveal of Joan as an accordionist, and that time she smashed a vase on his head – he’d be in the gutter where he belongs.
55) Father John Gill
Played by: Colin Hanks
First Appearance: “Three Sundays” (Season 2, Episode 4)
Despite being the highest-ranking religious authority on Mad Men, Father Gill was pretty hip to the times. He enlisted Peggy to write copy for the church’s teen social, and learned how to play guitar while in Rome. He’s also a total babe, explaining Gill and Peggy’s mutual attraction. But then Anita went and brought up Peggy’s pregnancy during a confessional, and Gill got pretty pushy about the whole “salvation” thing. His heart was in the right place, but giving Peggy an Easter egg “for the little one?” Dick move, Father.
54) Suzanne Farrell
Played by: Abigail Spencer
First Appearance: “Love Among the Ruins” (Season 3, Episode 2)
The buildup to Don’s relationship with Sally’s third grade teacher was pretty enticing, as it was back during a time when Don was at least attempting to stay faithful to Betty. But the culmination of it was an affair not to be remembered. Suzanne gave Don another young man in need of an identity change to mentor (in this case, her epileptic younger brother), and introduced him to the concept of jogging. Other than that, she was a spring fling that wound up quickly forgotten.
53) Gail Holloway
Played by: Christine Estabrook
First Appearance: “A Little Kiss, Part 1” (Season 5, Episode 1)
The passive-aggressive mother to end all passive-aggressive mothers, Gail Holloway is responsible for many of Joan’s characteristic traits. She’s sharp-tongued, able to expose other people’s insecurities, and knows how to get men to lend a hand. She may not have been a big help to Joan during her marriage to Greg, but is, by her own admission, proud of what Joan has accomplished with her career. If you’re looking for a babysitter or a backhanded compliment, you go to Gail.
52) Diana Baur
Played by: Elizabeth Reaser
First Appearance: “Severance” (Season 7, Episode 8)
Arguably the character whose ranking will be most subject to shifting after the finale, it’s not exactly clear what Diana is supposed to be to Don, or Mad Men. Is she a mirror of Don, an amalgamation of his past mistakes, or just a woman from Wisconsin trying to start her life over? It seems just as likely that the whole series finale be exclusively about Diana as it does that she never appears again. She’s certainly left an impression on the final season – we’ll just have to wait and see whether that impression is ultimately a good or bad thing.
51) Adam Whitman
Played by: Jay Paulson
First Appearance: “5G” (Season 1, Episode 5)
Yes, Don did accidentally blowup his commanding officer, but arguably the biggest casualty from his change of identities was half-brother Adam. Abandoned by Dick, Adam went on to live a modest life that was ruined the moment he tried to reestablish contact with his brother. Throwing money at Adam to make him go away is one of the worst things Don has ever done, leading to Adam hanging himself. Adam gets plenty of sympathy points, but is handicapped by his post-mortal employment as a metaphor-dispensing ghost dentist (“It’s not your tooth that’s rotten!”).
