Let’s get straight to the point: nearly every character in “Mad Men” has their flaws. However, there is an exception with Kiernan Shipka’s portrayal of young Sally Draper, who emerges as the show’s unlikely heroine. Matthew Weiner’s brilliant, introspective exploration of 1960s American culture, seen through the lens of the charming yet morally ambiguous ad executive Don Draper (played by Jon Hamm), stands as a pinnacle of television excellence and a quintessential representation of what many consider the “golden age” of TV. Hamm delivers an outstanding performance as Don, a man whose real identity is Dick Whitman. He assumes the identity of his superior officer during the Korean War and lives under this guise, unbeknownst to most of his acquaintances. Surrounding Hamm’s Don are stellar performances from actors like John Slattery as Roger Sterling, Elisabeth Moss as Peggy Olson, Christina Hendricks as Joan Holloway, and January Jones as Betty Draper, each bringing depth to their roles.

“Mad Men” is populated with compelling and absorbing characters, yet some are undeniably challenging to watch. Whether due to their overtly vile nature, their wearisome antics, or their sheer malevolence, certain characters can be hard to bear. This list ranks the most problematic main characters on “Mad Men,” whose actions might shock viewers but remain strangely captivating nonetheless. Here are the most notorious characters on the show, ranked.

Vincent Kartheiser’s portrayal of Pete Campbell in “Mad Men” often borders on the pitiable, making it almost difficult to categorize him among the worst. Almost. Pete, a privileged man buoyed by family wealth and indifferent parents, makes his debut as a junior accounts executive at the firm initially known as Sterling Cooper. He quickly takes an interest in Peggy Olson on her first day at work. Given fidelity’s loose interpretation within the narrative, Pete initiates a tryst with Peggy—in the office, no less—before the workday begins. Even after discovering that Peggy bore and subsequently gave away a child from their encounter, Pete remains largely unrepentant, eventually “settling down” with his wife Trudy, played by the exceptional Alison Brie.

Pete Campbell, played on “Mad Men” by Vincent Kartheiser, can be so unbelievably pathetic at times that it almost feels mean to put him on this list. Almost. An overtly spoiled man with a ton of family money and horrible, uncaring parents to go along with that money, Pete is introduced as a junior accounts executive at the firm initially named Sterling Cooper who takes a liking to Peggy Olson during her very first day of work. Because fidelity isn’t really a concept on “Mad Men,” per se, Pete consummates his relationship of sorts with Peggy — in the office before everyone arrives for the day, no less! — and although he later learns that she gave birth to and subsequently gave away a child that was the result of said consummation, Pete is fairly unrepetant about the whole thing and “happily” “settles down” with his wife Trudy (a particularly excellent Alison Brie).

Don’t get us wrong, Pete is funny — Kartheiser’s line reading of “Not great, Bob!” as Pete yells at James Wolk’s Bob Benson is so great that it ended up spawning a long-running meme of the quote — but he also gets in his own way, isn’t kind or generous to the people around him most of the time, and can be absolutely infurating to watch. When you do meet his parents, you understand him a little better (in that his father is a cold and hateful man who seems to openly despise Pete), but still, there’s no excuse for a lot of Pete’s behavior, particularly his implied sexual assault of a young German au pair who works for a family in his Manhattan apartment building. Pete might be enthralling at times, but he also kind of sucks.

Megan Calvet, played by Jessica Paré, doesn’t appear until Season 4 of “Mad Men” as a part of the typing pool at the firm now known as Sterling Cooper Draper Pryce (after Roger Sterling, Don Draper, Robert Morse’s Bert Cooper, and Jared Harris’s Lane Pryce join forces to launch their own ad company), but she’s a major part of the show. Why? Well, she becomes Megan Draper, Don’s much-younger second wife after he and Betty split up for good in the show’s third season. Like Paré herself, Megan canonically hails from Montreal in Canada and, as such, is fluent in both French and English; despite her humble beginnings as a typist, Megan is incredibly intelligent, has big dreams of becoming an actress, and actually matches strangely well with Don after his extremely hasty marriage proposal.

So what makes Megan one of the “worst” characters on “Mad Men” at the end of the day? Unfortunately for both the character and Paré — who turns in a genuinely great performance — Megan’s attempts to keep Don in line and faithful to her range from slightly awkward to outright humilitating (who can ever forget where they were when they watched her utterly bizarre performance of “Zou Bisou Bisou” in the show’s Season 5 premiere?!) Megan is ultimately a victim of Don’s openly terrible behavior, but it doesn’t make her easier to watch, complex though she might be. Unfortunately for Megan, who’s basically the physical embodiment of Don’s midlife crisis and mental breakdown towards the end of “Mad Men,” her presence in the show’s later seasons can be difficult to witness.

It’s a testament (pun intended) to how much Father John Gill sucks on “Mad Men” that, across just a few episodes of screen time, he still manages to make this list. Throughout Season 2 of the series, Father Gill — played by Colin Hanks — interacts mainly with Peggy Olson in his capacity as a member of a visiting ministry at her church in Brooklyn, New York, and the way he treats Peggy is legitimately shameful. As previously discussed, Peggy had a baby out of wedlock thanks to her tryst with Pete and ultimately gave the baby up for adoption after giving birth; because this was the 1960s, women were held accountable in particularly strict ways for behavior like this. That accountability takes an unfortunate human form in Father Gill.

Some might argue that Father Gill only intends to help lead Peggy down a better path, but by mining her for wisdom on how to write and speak to a crowd — based on her own talents as a copywriter — and still holding her accountable for the sin of her unintended pregnancy, Father Gill acquits himself in a way that’s frankly not fitting for a man of the cloth. Peggy is a powerhouse character, and thankfully, she isn’t dragged down by Father Gill past Season 2 of “Mad Men” — and he never reappears, which also effectively puts an end to Peggy’s further exploration of religion after her pregnancy.

Like we said, almost every single character on “Mad Men” is “bad” in one way or another, but Greg Harris, played by Samuel Page, is downright evil. Introduced as Joan Holloway’s handsome young fiancé in Season 2 — providing a stark contrast to Roger Sterling, who’s been Joan’s lover on the down low for quite some time — Greg establishes himself as a horrible, terrible, evil person by sexually assaulting Joan (in pretty violent fashion, to be honest) in the Sterling Cooper offices as an outright reaction to her obvious rapport with Roger. Things do not improve from there. When Greg isn’t chosen as the chief resident in his surgery program — because he’s frankly not talented enough but was hoping to skate by on family connections — he throws a tantrum so vile that Joan eventually physically attacks him by breaking a vase over his head, and after that, the couple finds a very era-appropriate way to separate from one another: Greg enlists as a medic in Vietnam.

While Greg is gone, Joan gives birth to a son named Kevin (who is not Greg’s biological child, but was actually fathered by Roger) and waits patiently for her husband to return from war — but when he does, he still sucks. After Greg pretends he’s being forced to return, only to reveal that he’s lying and can absolutely op out of another stint in Vietnam, he tells Joan that serving makes him feel like a good man. In one of Joan’s best and most cutting moments, she tells him, “You’re not a good man. You never were. Even before we were married, and you know what I’m talking about.” Joan ultimately raises Kevin on her own, which is definitely for the best.

Unfortunately, the “protagonist” of “Mad Men,” Don Draper, does earn the top spot on this list … because even though he’s endlessly compelling to watch, he can most accurately be described as “handsome garbage.” Not only is he a literal identity thief — seriously, who steals dog tags from a corpse and pretends to be that person?! — who lies to everybody around him about everything from his upbringing to his real name, but Don is often cruel, unbelievably selfish, and by any modern standards, he’d be classified as having a very serious drinking problem.

That last part is only important insofar as Don can be at his absolute worst as a human being when he’s drinking, but there’s not much in the way of evidence to suggest that he’d have many redeeming qualities if he quit drinking; he even essentially abandons his only “true” friend Anna Draper (Melinda Page Hamilton), the widow of the real Don Draper, as she’s dying across the country by missing her phone call. Despite occasional efforts, Don is a bad father, a terrible partner and husband, and not even always great at his job — even though his defining quality as an ad man appears to be that he can craft a campaign from whole cloth on the spot (because of course, he never prepares anything). Even Don’s final moments on the show feel as shallow as he often is as he “finds inner peace” in meditation, only to, as the show suggests, use that experience to craft a Coca-Cola ad. Don is compulsively watchable, and he’s also horrible.

“Mad Men” is available to stream on HBO Max and AMC+.

If you or anyone you know needs help with addiction issues, help is available. Visit the Substance Abuse and Mental Health Services Administration website or contact SAMHSA’s National Helpline at 1-800-662-HELP (4357).

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN’s National Helpline at 1-800-656-HOPE (4673).