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The secondary cast of Sterling Cooper (Seasons 1-3) in Mad Men. Beware of spoilers.

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    Harry Crane
Played By: Rich Sommer

"Oooh, a Negro homosexual, Canadian sexpot, and unaccompanied redhead. This may be my key demographic."

A media buyer at Sterling Cooper notable chiefly because everyone tends to overlook his existence, he eventually gets the agency into the television game, becoming Head of Television. He skips to SCDP to do the same job, where he finally has the resources to be effective... and somehow manages to end up even more of a schlemiel and a milquetoast (despite his good work).

  • '50s Hair: Starts off looking like a nerd from that era with slicked hair.
  • '70s Hair: Throughout the 60s he starts experimenting with the Peacock and Mod fashions of the era, even growing out his hair and ends the series with a very full hairdo with long side burns.
  • Ambiguously Bi: Harry Crane gives off vibes of this. On at least two separate occasions, he's talked about how a different character is "queer". His crass jokes about what he'd do to Megan reek of Have I Mentioned I Am Heterosexual Today?, and in "Tea Leaves" he talks about how good Charlton Heston looks naked. On the other hand, he's definitely had drunken one-night stands with women (his wife exiles him to the couch for it), so it's fairly likely he has some natural inclination towards women.
    • And then there's Joey's reaction to Harry's attempts to befriend him by telling him he could get him on Peyton Place:
    Joey: "Everyplace I've worked, there's always some old fairy who comes on to me, but that was the weirdest by far."
  • Butt-Monkey: Very often.
  • Casanova Wannabe: SO hard. In a series where Everybody Has Lots of Sex, he's the guy who never, ever, manages it on his own merits. After his drunken, regretted one-night-stand in season 1, the only time we see him get any, it was being used on him as a bargaining chip by Lakshmi to get him to back off from helping Paul.
  • Characterization Marches On: In the first two seasons, he was completely devoted to his wife, being legitimately repentant that he had a drunken one-night stand and cheated on her. In the more recent seasons, he Took a Level in Jerkass and is an outright braggart over how often he cheats on his wife.
  • The Chew Toy: To the point where Harry missing his chance at becoming a partner at the moment where being one would have made him a millionaire is played for laughs.
    • And then in the following episode, he loses even more money in a messy divorce.
  • Demoted to Extra: Despite still being technically a regular character in the second half of Season 7, his role is reduced to the point where he gets barely any more focus than the various secretaries. Even in the series finale, the only thing he gets to do is go to a farewell lunch with Pete.
  • Dude, Where's My Respect?: Harry constantly complains that he's passed over for a partnership, despite being indispensable to the firm. Heavily Lampshaded in the episode A Tale of Two Cities, where he understands exactly how Hollywood works while Don and Roger are fish out of water — but Don and Roger are convinced that all their errors are the fault of the people in California, not their unwillingness to listen to Harry.
    • By season seven, he has given up on trying to earn respect and becomes a Deadpan Snarker who has no problem with calling out his bosses for ignoring the media department until it bites them in the behind.
  • The Friend Nobody Likes: Even Pete and Cutler can barely stand Harry and his smarminess.
  • Happily Married: For the longest time, he fits this trope best out of the married men in the office — he did cheat on his wife once, but it was a drunken one-night stand, he clearly regretted it immediately, and he must have told her, because it's doubtful she could have found out any other way. He was temporarily Exiled to the Couch for it and then forgiven (between seasons). She also has a job of her own and he often takes her advice on work matters. Subverted in Season 4, where he is seen flirting with a model, and in Season 5 it is revealed that he has become unhappy with his marriage and cheats on his wife once more. In "Waterloo", he mentions that his wife is considering divorcing him.
  • Hidden Depths: He's clearly succeeded despite having fewer advantages than Pete or Ken — he didn't go to an Ivy League school, for instance, and doesn't seem to have their connections. He is ahead of his time on the importance of television. He was also a photographer in college.
  • Jerk with a Heart of Gold: Helps Kinsey out when Kinsey is at his lowest.
  • Laser-Guided Karma: Harry spends the latter seasons trying desperately to assert himself as a pivotal member company, eventually chasing after a position as Partner. When he finally gets an offer, he dicks around trying to play hardball with the negotiations. Naturally, at the halfway point of Season 7, he waits too long to sign the contract and misses an opportunity to make millions.
  • Nerd Glasses: Transitions in style from rounded browlines in the first half of the 1960s to a black and angular thick-framed variety post-Season 4.
  • Skewed Priorities: He is upset at learning of Martin Luther King Jr.'s death not because a great man who brought hope to millions died, but because the media coverage of his death is preempting programs in which SCDP's commercials were supposed to air, costing the agency money. Pete, of all people, calls Harry out on his insensitive behavior.
    • It's hinted that he had this as early as Season 3. Following JFK's death, Pete notes to Trudy that Harry was, of all things, checking his data to see what programs wouldn't be aired as a result.
  • Took a Level in Jerkass: At the beginning of the show he was one of the nicest guys in the office, but after his Television department takes off at SCDP, he starts to suffer from a massively inflated ego, not to mention becoming far more overtly sexist. By series' end, nearly ever major character seems to openly loathe him.
  • What You Are in the Dark: Helped Kinsey out even though no one, not even Kinsey, would ever know the full extent of the help.
  • Your Cheating Heart: He had a one-night-stand early in the show and was wracked with regret, but by the later seasons he was shamelessly using his TV connections to have sex with any women in eyeshot.

    Ken Cosgrove
"I wanna stand and salute that."
Click here to see  Ken's appearance starting from "The Quality of Mercy".

Played By: Aaron Staton

"Title"? I'm Ken!...Cosgrove...Accounts.

Columbia-educated WASP from Vermont and a major rival of Pete's, coming in as an account executive at about the same time as him. They eventually come to a truce.

  • '50s Hair: This is especially noticeable in the first three seasons; it loosens up into the late 60s "Dry Look" over time.
  • The Ace: He can dance and write, in addition to being a good salesman.
  • Actually Pretty Funny: In response to Roger's pirate crack when wearing the eye patch after being accidentally shot by a couple of GM executives, he says he'd laugh if he didn't hurt so much.
  • Almighty Janitor: Roger offers to promote Ken to partner in exchange for Ken getting his father-in-law to sign on as an account. Ken turns him down because he does not want to get involved with any of the office politics.
  • Always Someone Better: He's the target of envy from Pete, Harry, and Paul.
  • Break the Cutie: The Chevy execs drive him crazy, involving him in a car crash and later shooting him on a hunting trip — enough to make him give the Chevy account to Pete.
  • Butt-Monkey: In Season 6, courtesy of some rowdy executives of General Motors. A car accident leaves him walking with a cane and shortly after he needs an eyepatch thanks to a hunting accident. Then he calls it quits and hands the account to Pete.
  • Character Development: Actually done rather subtly, but Ken's has steadily changed over the course of the series. In the early series, he was a bit of a Jerkass Womanizer who had no problem taking advantage of the office politics. After settling down and getting married, Ken mellowed out, becoming faithful to his wife and transitioned to being an all around nice guy. By latter seasons, Ken is the only member of the office able to balance his work and personal life.
  • Chivalrous Pervert: In the early seasons, he's every bit the womanizer that his peers are, but unlike them, Ken is never shown to be manipulative or condescending towards the females he's hitting on. He treats Peggy with respect and tries (unsuccessfully) to court Jane before he finally gets engaged and remains faithful to his wife.
  • Even the Guys Want Him: Oh, poor Sal.
  • Eye Scream: He loses an eye to a hunting accident in Season 6.
  • The Generic Guy/Satellite Character: Ken seems to exist primarily to act as a foil for other characters. Paul Kinsey and Pete Campbell are jealous of Ken's literary ability, Sal Romano is attracted to him, and Ken's refusal to mix SCDP business with his personal life in Season 4 serves to contrast with most of the other account men at SCDP. Early in season 1, Ken was also a Charismatic Womanizer while Harry was a stiff who kowtowed to his wife. In later seasons, Ken is now Happily Married while Harry callously cheats on his wife.
  • Happily Married: To Alex Mack.
  • Hidden Depths: For all his bluster and inappropriate behavior, he respects Peggy and treats her relatively equally much faster than any of the other characters in his generation.
    • It was already known that Ken had written and published one story, but Season 5 reveals he's published over 20 science fiction and fantasy stories under a pseudonym, something he's mildly embarrassed about but that both his wife and Peggy seem genuinely impressed by. When Roger finds out, he's less impressed, giving Ken a tongue lashing for dividing his focus.
  • Most Writers Are Writers: During season one, he fiddled around with getting some of his writings published, much to the jealous fury of Pete. When it turns out he's succeeding, it's Roger's turn to be jealous.
  • Nice Guy: Ken has a few obnoxious moments in early seasons, but eventually becomes the most decent, likable, and honest person in the office.
  • No Good Deed Goes Unpunished: In season 4, Ken quits his position at McCann when he's approached by the Partners to start working for SCDP. This ultimately comes back to bite him in Season 7 where after McCann buys out SC&P, McCann makes it his first priority to fire Ken for previously quitting. The real kicker is Roger doesn't even try to fight for his job.
  • Only Sane Employee: So far, Ken seems to be the only character whose work has never been affected by a secret personal life, blatant narcissism, excessive drinking, the inability to keep his pants on, spinelessness, or any of the other deep character flaws everyone else seems to have.
  • Platonic Life-Partners: With Peggy in Season 5.
  • Politically Incorrect Hero: His rather old school prejudice against the Irish is what gets him fired after the McCann-Erickson takeover. And that doesn't even stop him making more remarks.
  • The Reliable One: Throughout the early seasons, the senior staff actually favored Ken over Pete Campbell. He doesn't advance like others because of his refusal to get involved in any of the office politics.
  • Took a Level in Jerkass: In "Time Zones", the stress from managing virtually every account in SC&P's New York office has done a number on Ken's temper.
    • Though these are mostly restricted to times when he is under extreme duress. He seems more apologetic to Joan for his irritability later, and he's genuinely pleased to see Don in "Field Trips". He specifically notes how much the carousel in Central Park reminds him of Don, serving as a heartwarming Call-Back to Don's speech way back in Season 1's "The Wheel" (which would've occurred almost a decade a go, in-universe).
  • Tranquil Fury: In Season 7's "Severance," in response to getting fired by Roger and McCann, Ken takes over his father-in-law's position at Dow Chemicals and then tells Roger and Pete calmly that they will be needing to please him now.
    • After stringing them along for a few months, Ken gleefully fired them when doing so would kibosh SC&P's attempt to move to California and maintain autonomy from McCann.

    Paul Kinsey
Played By: Michael Gladis

A wannabe Bohemian copywriter. He doesn't transfer to SCDP with the rest of the cast.

  • '50s Hair: Starts off with a groomed look of the era, adds a goatee, and then ends up with no hair.
  • Bourgeois Bohemian: Grows a beard to put on the facade that he's "with it" among the righteous youth.
  • Butt-Monkey: More and more as Peggy rises through the ranks.
  • The Chew Toy: Is the butt of a lot of demeaning jokes. Even Lois, one of the more incompetent employees, tells him he's likely not going to get rehired post-merger due to redundancy.
  • Deadpan Snarker: He has no problem making fun of things that annoy him.
  • Giftedly Bad: Fancies himself a talented writer. The show is constantly providing evidence to the contrary.
    • Compared to Peggy, his work as a copywriter is mediocre at best. Some episodes indicate that he has good ideas, but no follow-through.
    • His coworkers discover a play he has written and act it out. No one is impressed.
    • His return, after being Put on a Bus, reveals that he has been fired from a number of copywriter jobs at other agencies.
    • He presents Harry with a spec script he has written for a Star Trek episode. He is very proud of his work, calling it the best thing he has ever written. Harry, Peggy, and even Paul's girlfriend agree that it's terrible.
    Harry: I think it was really hard for him.
    Peggy: Then he shouldn't be doing it.
  • Green-Eyed Monster: He's jealous of Peggy's success (not that he does anything about it).
  • Hidden Depths: Was a talented a capella singer at Princeton, and sung in their choir.
  • Hipster: Of the period's definition of the word, although to be frank he'd fit right in with today's hipsters, too.
  • Humiliation Conga: After he is not invited to join SCDP, he works for McCann Erickson but is fired. He then goes through a series of jobs at other agencies until he is reduced to work as an in-house copywriter for A&P. Then he loses that job as well.
  • Joisey: He apparently had a really thick accent before he went to Princeton. He still lives in New Jersey through the early seasons (Season 2 opens at a party at his apartment in Montclair).
  • Know-Nothing Know-It-All: He's very pretentious and arrogant, though it's repeatedly made clear that he's something of a dunce and everyone eventually comes to see that Peggy and Smitty are more talented copywriters.
  • Morality Pet: In "Christmas Waltz", he becomes Harry's.
  • Most Writers Are Writers: He tries, anyway.
  • Old Shame: It's revealed that he went to Princeton on a scholarship in season 3, implying he's from lower-class roots and he doesn't want anyone else to know.
  • Pride: His inflated, sensitive ego makes him hard to get along with and contributes to his Butt-Monkey status, but the really fatal example of this can be inferred from offscreen. When Crane asks Peggy why Kinsey was never brought on at SCDP, she responds that he never applied, suggesting that his pride was too bruised to consider that they might have given him a second shot. Contrast to Cosgrove, who was also left behind initially but made his way back to SCDP in short order.
  • Put on a Bus: He isn't hired by SCDP and thus leaves the cast after Season 3.
    • The Bus Came Back: After being absent for the entirety of Season 4, he shows up once more in Season 5's "Christmas Waltz," where it is revealed that he has joined the International Society for Krishna Consciousness. At the end of that episode, he is put more literally and permanently on a bus, to Hollywood by Harry Crane.
  • Shock Value Relationship: He dates a black woman to show how "progressive" he is. It doesn't take her long to figure it out.
  • Small Name, Big Ego: A fairly frail ego at that.
  • Soapbox Sadie: Against the destruction of Penn Station.
  • Some of My Best Friends Are X: In an attempt to show how progressive he is to his black girlfriend, Paul pretends he's on a first name basis with the African American elevator attendant.
  • The Unfavorite: Has very clearly become this compared to Peggy by mid-late Season 3, with Don considering him a spent force creatively and being thoroughly sick of his politics. Harry even admits privately to Pete in Season 5 that even if the McCann-Erickson buyout hadn't gone ahead, then sooner or later Don would probably have fired him anyway.

    Sal Romano
Played By: Bryan Batt

Head art director at Sterling Cooper, and a closeted gay man. He leaves just before the end of Season 3 for reasons that have to do with Sterling Cooper's main client being a huge dick.

  • '50s Hair: Has a stylized, but slick and masculine look from that era.
  • The Beard: His wife, Kitty.
  • But Not Too Gay: Justified given the time period, and the fact that Sal is extremely careful and conscientious. He's had his opportunities, but has turned (most of) them down.
  • Dropped a Bridge on Him: In a rare case of it, he's not killed off, but once Sal is outed, he gets sent his walking papers, and was never seen or mentioned again.
  • Gayngst: Justified, given the period setting.
  • Have I Mentioned I Am Heterosexual Today?
  • Latin Lover: His Italian heritage makes him automatically attractive to at least one doe-eyed secretary that we know of, and he plays this trope up for maximum cover. It probably also provides an explanation in the minds of his WASPy colleagues for his slight flamboyance.
  • Put on a Bus: In Season 3, when he's fired by SC.

    Herman "Duck" Phillips
Played By: Mark Moses

Brought into Sterling Cooper after his Dark and Troubled Past at the London office of Young & Rubicamnote . His decisions result in frequent clashes with others (especially Don), but he gets the job done. Gets a job with agency Greynote  after PPL sells Sterling Cooper to McCann Ericksonnote . He eventually becomes a headhunter that many of SC&P's staff use.

  • '50s Hair: Has the Standard '50s Father look, then close cuts his hair, and then ends the series with slightly looser hair.
  • Appropriated Appelation: Implied:
    Duck: Please, call me "Duck".
    Don: I was told not to call you "Duck".
  • Big Bad: He, more or less, serves as this in season 2, becoming Don's Arch-Enemy within Sterling Cooper. Most of the drama stems from their inability to agree on how to run the agency, working instead to outsmart and undermine each other.
  • Dark and Troubled Past: His career at Y&R was ruined by his alcoholism and an affair.
    • He also killed seventeen men at Okinawa.
  • I Know Kung-Fu: He can handle himself in a fight, as Don learns in "The Suitcase".
  • Jerkass: Probably the most ruthless in office politics while at Sterling Cooper, though he tries to camouflage it with a fatherly demeanor. It doesn't fool anybody.
  • Kick the Dog: When he lets his dog Chauncey go on the streets of New York because he's bothered by it looking at him while drinking. After the conversation with Pete earlier in the episode (where Pete says he loves having Chauncey around and wants a dog "for the office"), it's clearly done to show that Duck is not a nice person.
  • May–December Romance: With the decade or so younger Peggy.
  • Nice Job Breaking It, Hero!: He persuades Sterling Cooper to get rid of their existing regional airline client in order to bring in American Airlines, which backfires horribly when his contact at the airline is fired right before the scheduled pitch, killing the deal there and then. Roger calls him out on this when he requests to be made partner, pointing out that thanks to the mess, the company is actually worse off than they were when he was brought in.
  • Off the Wagon: As we later discover.
  • Smoking Hot Sex: Of its many practitioners on the series, none is quite as avid as Duck, particularly during his affair with Peggy.
  • Smug Snake: He's not nearly as good at office politics as he thinks, as Don effortlessly spoils his attempt to use the PPL merger to make himself company president.
  • Standard '50s Father: Divorced though he may be, this is clearly an image he's cultivated for himself.
  • Start of Darkness: While he was never that nice of a person, he was at least no worse than Don, Roger or Bert were. The combination of his attempted deal with American Airlines being sunk by misfortune, along with his wife cutting off access to his children sends him down a dark path, and he goes From Bad to Worse after Roger scornfully turns down his request to be made a partner in the company.
  • Tyrant Takes the Helm: For all of a couple of minutes.
  • Villainous Breakdown: Gradually becomes more stressed out over his time at Sterling Cooper. It gets even worse when he falls off the wagon. This culminates in his ragequitting Sterling Cooper after Don effortlessly foils his plan to use the merger to become company president. It reaches its climax in Season 4, when he drunkenly disrupts the Clio award ceremony, then breaks into the SCDP office to take a crap on Don's chair (where Peggy finds him after he almost does it in Roger's office by mistake). He seems to have got his act together again by Season 6's "The Better Half".
  • We Used to Be Friends: "Friends" is stretching it a bit, but he and Don were initially on much better terms. After all, it was Don who hired Duck in the first place.

    Freddy Rumsen
Played By: Joel Murray

An avuncular copywriter who, despite being a little old and behind the times, is generally open and fun-loving. He's a big supporter of Peggy, though they have their disagreements. Has had problems with alcohol, but is presently on the up-and-up.

  • The Alcoholic: Joan in Season One makes a snarky remark about his drinking habits after he expresses amazement at Peggy's wordplay ("Wouldn't you like to put that in a drink") and Season Two shows that his drinking led to him performing Mozart by unzipping his fly out in the steno pool and peeing his pants during a meeting. This leads to him getting fired and becoming freelance.
  • The Bus Came Back: In Seasons 4, 5, and 7A.
  • Chew Toy: Pretty much exists to be the butt of Roger's (and Don, to a lesser extent) jokes.
  • Playing Cyrano: In the Season 7 premiere, we find out that during his "leave of absence", Don gets Freddy to go into SC&P as a front to give pitches Don wrote so he can still work. Freddy lampshades this to Don later by calling it "This Cyrano routine".
  • Token Good Teammate: Of the older and more conservative men in Sterling Cooper. He is faithfully married to his wife and stands for her honor when someone implies she's unattractive and he's awful in bed, he doesn't make degrading remarks about the secretarial pool during the focus group test for Belle Jolie lipstick, he was the first to notice Peggy's talent for words, and he is more involved with his family affairs all in contrast to men like Roger, Don, Lane, Pete, and Harry.

    Jane Siegel
Played By: Peyton List

Jane is a college graduate hired as Don's secretary in Season 2. She quickly gains Joan's mistrust with her attention-grabbing wardrobe choices and the rather unsubtle flirting with the male colleagues. The relationship with Joan quickly sours and Joan would have fired her if not for Roger's intervention. Roger then starts an affair with her and divorces Mona to get with Jane, despite the embarrassing fact that she's not much older than Roger's daughter.

  • Amicable Exes: Retains an amicable relationship with Roger after their marriage ends in Season 5, and attends his mother's funeral in Season 6.
  • Awful Wedded Life: Her marriage with Roger quickly sours as their are too much apart in age and Roger is simply unable to be faithful.
  • Conspicuous Consumption: After her marriage with Roger her outfits get really flashy, and she goes visiting her former office exactly to flaunt them.
  • Dude Magnet: Several male characters hit on her when she joins the office, most of all Ken and Roger.
  • The Fashionista: She spots some of the trademark 60s trends, and she's notably one of the first female characters to get a tan.
  • Foil: Initially serves as one to Joan, although Joan starts quickly to dislike her because she finds her flirty attitude utterly unprofessional.
    • To Megan. Jane is a secretary with artistic interests and writes poetry as an hobby, while Megan herself is an aspiring actress. Also they are young, twenty-somethings who have an affair with their married bosses and then marry them. Roger even lampshades their similarities to Don.
  • Gold Digger: It's easy to establish her as one, as she initially was set in pursuing Don and let down Ken because she clearly thought he wasn't enough for her. It's clear that she had her eyes set on a partner, but it's hinted that she may have really loved Roger after all.
  • The Missus and the Ex:
    • Much drama is made for Roger's daughter's wedding because Margaret is embarrassed that her stepmother looks like her older sister and wants to give her advice on men. Mona wins the round mediating between the member of this family displaying much more tact.
    • Although she doesn't know, Joan was Roger's other woman. Roger would call Joan to complain about his current matter of states, even cracking a Joel at Jane's expenses. And eventually cheats on Jane with Joan.
  • Informed Judaism: Siegel may be a Jewish last name, but not always. Latter seasons inform us that she's Jewish (and she can speak Yiddish).
  • Peer Stepparent: Margaret Sterling is utterly distressed by the fact that people will notice her stepmother is young enough to be her older sister. Jane tries to play the Cool Big Sis card to gain her affection but it creeps Margaret even more.
  • Trophy Wife: Quite a stereotypical example, although Jane is more a pitiable character than anything. Roger does not take her seriously and eventually cheats on her with multiple women, her stepdaughter and in-laws barely acknowledged her and she's rather lonely.
  • Yiddish as a Second Language: She speaks Yiddish while high on drugs. Roger mistakes it for German.


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