From debauched ad executives to their frustrated housewives, Mad Men is full of great characters. Mad Men had some of the best writing in TV history, and that started with its characters. Matthew Weiner and his team of writers came up with an ensemble of well-rounded, three-dimensional, deeply human characters, each with their own distinctive personalities, flaws, goals, and insecurities.

Mad Men’s cast was stacked with incredible actors, from Jon Hamm to Elisabeth Moss to John Slattery to Christina Hendricks, who brought those characters to life with aplomb. The series immersed viewers in the 1960s so well because the actors felt like they’d stepped out of that era. Hamm is practically Cary Grant; Hendricks is practically Marilyn Monroe.

Bert Cooper

From our perspective as a modern audience, the characters in Mad Men all seem fusty and old-fashioned, with outdated views. But Bert Cooper was fusty and old-fashioned and antiquated even by their standards. Bert isn’t a fan of the free-spirited attitude of the Swinging Sixties, but the times they are a-changin’ whether he likes it or not.

Bert died of amazement watching the Apollo 11 landing, highlighting just what a big deal it was at the time. Don’s posthumous hallucination of Bert doing a song-and-dance number in the office ensured audiences would remember this character for the long haul.

Trudy Campbell

Before Community, GLOW, and Together would make Alison Brie a full-blown icon, she was a scene-stealing supporting player in Mad Men. Trudy Campbell was the quintessential 1960s housewife, forced to cater to her husband’s fragile male ego while keeping her own problems to herself, but she came from a lot more money, which created an interesting power imbalance in their marriage.

As the series went on, Trudy was given more and more agency. She eventually got so frustrated with Pete that she left him, and she only became more confident and empowered after that.

Duck Phillips

Duck Phillips was great at his job as Head of Account Services — he had the vision and the industry insight to keep Sterling Cooper on track — but he wasn’t a good political fit for the office. Duck’s story shows that you can be really good at your job and still tank your career if you don’t have people skills.

After leaving the agency, Duck came back at the exact right time to solidify his legacy as one of the show’s best characters in Mad Men’s greatest episode, “The Suitcase.” Just when you think you can predict where the episode is going, Duck shows up and gets into a drunken fight with Don.

Ken Cosgrove

Ken Cosgrove might have been the best writer at Sterling Cooper, because his writing talent extended beyond coming up with advertising slogans. He saw his ad work as an easy paycheck; his true passion was fiction, and he had some success publishing short stories and working on a couple of novels.

He was set up for an illustrious career as an author, but he ended up getting one of Mad Men’s most tragic arcs. After losing his eye and getting ousted from the firm, he gave up his literary aspirations, jumped headfirst into the rat race, and became consumed by corporate vengeance.

Megan Draper

Don’s second wife (third, technically, if you count Anna Draper) was introduced as more of an idea than a three-dimensional human being. Don’s relationship with Megan symbolized him moving on from Betty, crossing the line to sleeping with his secretary, and seemingly starting a new chapter of his life.

But as the relationship went on, Megan became an interesting character in her own right. What started off as a whirlwind fairytale romance quickly got a reality check. Don failed to stay faithful this time around, despite his best efforts, and Megan’s Hollywood aspirations kept pulling her to the other side of the country.

Bob Benson

Bob Benson was the subject of many a fan theory throughout Mad Men’s run. The show’s fans were desperate to figure out the true identity of this oddball account executive.

Was he living under a stolen identity like Don? Was he a government agent investigating Don? Was he just a run-of-the-mill conman? Whether any of these are true or none of them, the mysterious air around Bob made him a fan-favorite.

Marie Calvet

Megan’s acid-tongued mother, Marie Calvet, stole the show whenever she was around. She would tear people down with brutally biting insults that were 100% on-point. When she told Don that Megan didn’t have the talent for an acting career and he should just wait it out, it seemed harsh. But Megan ended the series a failing actress, so Marie was right.

Marie embodied the free spirit that Megan was always trying to tamp down. When Marie was charmed by Roger Sterling, she wasted no time beginning an affair with him. Megan was frustrated by her mother’s liberated impulsiveness, but she also envied it.

Freddy Rumsen

Mad Men makes day-drinking at the office look glamorous, but the season 2 storyline of Freddy Rumsen’s alcoholism destroying his career and reputation showed that it’s not so glamorous after all. Drinking in the office was a signature trope of Mad Men, but Freddy’s descent into addiction showed the dark side of that lifestyle.

Fortunately, Freddy’s story ultimately had a happy ending. He got clean and sober, became an AA sponsor, and landed on his feet professionally. He went from a laughingstock to one of the show’s most inspiring characters.

Jimmy Barrett

Patrick Fischler is one of Hollywood’s great character actors. He has a habit of popping up in a small role in a movie or TV series and completely stealing the show. His Mad Men role as Jimmy Barrett was no different. Jimmy was a snarky insult comic who did a campaign for Sterling Cooper.

Jimmy was an interesting foil for Don. Jimmy’s acerbic wit rubbed Don the wrong way, and Don’s affair with Jimmy’s wife rubbed Jimmy the wrong way. Fischler nailed the biting one-liners, but he also captured the smug arrogance underneath them.

Betty Draper

At the beginning of the series, Don was married to Betty, the mother of his children. She was the typical ‘60s housewife — staying home all day, raising the kids singlehandedly, turning a blind eye to her husband’s infidelities — but January Jones brought so much depth to that character.

By the end of the series, Betty had left Don, gotten remarried, and faced a long battle with cancer. Jones’ portrayal of Betty is both curiously emotionally distant and a triumph of the human spirit.