Pour a very 1960s office drink and sharpen the pitch. These 120 Mad Men trivia questions cover Don Draper, Peggy Olson, Joan Holloway, Roger Sterling, Betty, Pete, Sterling Cooper, famous campaigns, secret identities, office power, marriages, historical events, and seven seasons of advertising people trying to sell happiness while failing to live it.
Keep watching with our TV show trivia, 1960s trivia, and pop culture trivia.
Don Draper, Dick Whitman & the Draper Family
Q: Who plays Don Draper?
A: Jon Hamm.
Q: What is Don's profession?
A: Advertising creative director.
Q: What agency employs Don at the start?
A: Sterling Cooper.
Q: What is Don's birth name?
A: Dick Whitman.
Q: How does Dick become Don Draper?
A: He switches identity tags with a dead officer during the Korean War.
Q: Why does he take the identity?
A: To escape his traumatic past and military service.
Q: Who is the real Don Draper's widow?
A: Anna Draper.
Q: What relationship develops between Anna and Dick/Don?
A: Deep friendship and chosen-family bond.
Q: Who is Don's first wife in the series?
A: Betty Draper.
Q: Who plays Betty?
A: January Jones.
Q: What are Don and Betty's children named?
A: Sally, Bobby, and Gene.
Q: Who plays Sally?
A: Kiernan Shipka.
Q: What suburban community is the Draper home associated with?
A: Ossining, New York.
Q: What is Don's relationship with fidelity?
A: He repeatedly has affairs.
Q: Does Betty initially know Don's real identity?
A: No.
Q: What discovery damages their marriage deeply?
A: She learns about Dick Whitman and Don's hidden past.
Q: Who does Betty later marry?
A: Henry Francis.
Q: What is Henry's profession?
A: Political adviser and public official.
Q: What illness does Betty develop near the end?
A: Lung cancer.
Q: What does Betty decide about treatment?
A: She largely rejects aggressive treatment and focuses on her remaining life.
Q: Who does Don marry second?
A: Megan Calvet.
Q: Who plays Megan?
A: Jessica Paré.
Q: What is Megan's career ambition?
A: Acting.
Q: What song does Megan perform at Don's birthday party?
A: “Zou Bisou Bisou.”
Q: What does Don think of the performance?
A: He is embarrassed and uncomfortable.
Q: What happens to Don and Megan's marriage?
A: It deteriorates and ends.
Q: What personal problem does Don repeatedly fail to solve?
A: He can reinvent his image but struggles with intimacy, shame, addiction, and self-acceptance.
Q: What product does Don say “It's toasted” about?
A: Lucky Strike cigarettes.
Q: What makes Don a gifted ad man?
A: He turns fear, desire, nostalgia, and identity into simple emotional stories.
Q: Why is Don's false identity thematically important?
A: Advertising and Don both rely on carefully constructed stories about what people want to believe.
Peggy, Joan, Roger & Sterling Cooper
Q: Who starts as Don's secretary and becomes a copywriter?
A: Peggy Olson.
Q: Who plays Peggy?
A: Elisabeth Moss.
Q: What makes Peggy unusual in the office?
A: She enters a male-dominated creative profession and advances through talent and persistence.
Q: What product gives Peggy an early creative opportunity?
A: Belle Jolie lipstick.
Q: What does Peggy secretly experience at the end of Season 1?
A: She gives birth after not fully recognizing or confronting her pregnancy.
Q: Who is the child's father?
A: Pete Campbell.
Q: What happens to the baby?
A: Peggy gives the child up.
Q: What advice does Don give Peggy afterward?
A: Move forward as if it never happened.
Q: Does Peggy ultimately remain at Don's side forever?
A: No. She leaves for another agency, then later reunites professionally through mergers.
Q: Who is Sterling Cooper's office manager and later partner?
A: Joan Holloway Harris.
Q: Who plays Joan?
A: Christina Hendricks.
Q: What is Joan exceptionally good at?
A: Managing people, office systems, client needs, and power dynamics.
Q: Who does Joan marry?
A: Greg Harris.
Q: What is Greg's profession?
A: Doctor who later serves in the military.
Q: What happens to their marriage?
A: Joan ends it after abuse, resentment, and his decision to return to military service.
Q: Who is the father of Joan's son Kevin?
A: Roger Sterling.
Q: Who plays Roger?
A: John Slattery.
Q: What position does Roger hold?
A: Partner and account executive.
Q: What is Roger's father's connection to the company?
A: He co-founded Sterling Cooper.
Q: Who is Roger's first wife?
A: Mona Sterling.
Q: Who does Roger leave Mona for?
A: Jane Siegel.
Q: What psychedelic experience changes Roger's perspective temporarily?
A: LSD.
Q: Who is Bert Cooper?
A: Elderly co-founder and partner of Sterling Cooper.
Q: What does Bert famously avoid wearing in his office?
A: Shoes.
Q: What Japanese art does he collect?
A: Japanese prints and art, including a famous Hokusai print.
Q: What Ayn Rand influence appears in Bert's worldview?
A: Strong individualism and capitalist philosophy.
Q: What happens after Bert dies?
A: Don imagines him singing and dancing “The Best Things in Life Are Free.”
Q: What does Joan eventually launch?
A: Her own production company, Holloway Harris.
Q: What does Peggy achieve by the finale?
A: Senior creative authority and a more emotionally honest relationship with Stan.
Q: Why are Peggy and Joan essential?
A: Their careers show different ways women navigate and challenge a sexist workplace.
Pete, Clients, Agency Wars & the 1960s
Q: Who is ambitious account executive Pete Campbell?
A: A young Sterling Cooper employee from an old New York family.
Q: Who plays Pete?
A: Vincent Kartheiser.
Q: Who is Pete's wife?
A: Trudy Campbell.
Q: Who plays Trudy?
A: Alison Brie.
Q: What does Pete discover about Don?
A: His real identity as Dick Whitman.
Q: Does exposing Don work the way Pete expects?
A: No.
Q: What does Bert Cooper say about Don's secret?
A: Essentially that he does not care.
Q: What British company buys Sterling Cooper?
A: Putnam, Powell & Lowe.
Q: What new agency do key characters form?
A: Sterling Cooper Draper Pryce.
Q: Who is Lane Pryce?
A: British financial executive who joins the new agency as partner.
Q: Who plays Lane?
A: Jared Harris.
Q: What financial crime does Lane commit?
A: Forges Don's signature on a company check.
Q: What happens after Don confronts him?
A: Lane dies by suicide.
Q: What major cigarette client anchors early business?
A: Lucky Strike.
Q: Who is the Lucky Strike executive closely tied to Roger?
A: Lee Garner Jr.
Q: What happens when Lucky Strike leaves?
A: The agency faces a financial crisis.
Q: How does Don respond publicly?
A: Writes an anti-tobacco newspaper letter announcing the agency will not take cigarette accounts.
Q: What car company becomes a dream account?
A: Jaguar.
Q: What terrible deal helps win Jaguar?
A: Joan is pressured to sleep with a client executive in exchange for partnership equity.
Q: Does Don approve of the arrangement?
A: No, though he fails to stop it in time.
Q: What car company becomes the huge target late in the series?
A: Chevrolet.
Q: What rival agency merges with SCDP to pursue Chevrolet?
A: Cutler, Gleason and Chaough.
Q: Who is Ted Chaough?
A: Rival creative director who becomes Peggy's boss, romantic interest, and later colleague.
Q: What major advertising giant ultimately absorbs the agency?
A: McCann Erickson.
Q: What real historical assassination is depicted in Season 3?
A: John F. Kennedy's assassination.
Q: What moon event occurs in the 1969-set final season?
A: Apollo 11 Moon landing.
Q: What civil-rights assassination affects the office in Season 6?
A: Martin Luther King Jr.'s assassination.
Q: What cultural change does the series track?
A: The shift from early-1960s conformity through late-1960s political, sexual, racial, and generational upheaval.
Q: Does Mad Men treat advertising campaigns as isolated from history?
A: No. The business constantly reacts to social change and consumer anxiety.
Q: What makes the period setting more than decoration?
A: Changing norms expose how characters adapt, resist, or exploit cultural transformation.
Carousel, Finale & Hard Mad Men Trivia
Q: What Kodak product does Don famously pitch?
A: A slide projector.
Q: What name does he give it?
A: The Carousel.
Q: What emotional theme drives the pitch?
A: Nostalgia.
Q: What family images does Don use?
A: Photographs of his own marriage and children.
Q: Why is the pitch painful?
A: The happy images contrast with Don's damaged real family life.
Q: What does Don say nostalgia means?
A: A pain from an old wound, presented as a powerful emotional connection.
Q: What happens to Don professionally before the final season?
A: He is placed on leave after increasingly erratic personal revelations and behavior.
Q: What humiliating pitch contributes to that?
A: He reveals his childhood in a brothel during the Hershey presentation.
Q: What does Don eventually do after returning?
A: Works under reduced authority before regaining influence.
Q: What happens when McCann absorbs the agency?
A: The characters lose much of their boutique independence.
Q: Who adapts relatively comfortably to McCann?
A: Roger and eventually others find roles, while Joan encounters severe sexism and leaves.
Q: Why does Joan leave?
A: She is denied equal treatment and pushed out of her account authority.
Q: What does Joan do instead?
A: Builds Holloway Harris.
Q: What relationship finally becomes explicit for Peggy?
A: She and Stan Rizzo admit they love each other.
Q: Where does Pete move for a new job?
A: Wichita, Kansas.
Q: What company hires Pete?
A: Learjet.
Q: What happens to Pete and Trudy?
A: They reconcile and leave New York together.
Q: Where does Roger's romantic story end?
A: He marries Marie Calvet, Megan's mother.
Q: What does Sally do after learning Betty is dying?
A: Steps into a more adult caregiving role for her family.
Q: Where does Don go in the finale?
A: A California coastal retreat.
Q: What does he do in the final scene?
A: Meditates and smiles.
Q: What famous real commercial immediately follows?
A: Coca-Cola's “I'd Like to Buy the World a Coke” Hilltop ad.
Q: What does the edit imply?
A: Don may have transformed his spiritual experience into the iconic Coke campaign.
Q: Is it stated directly that Don created the real ad?
A: No, it is an artistic implication.
Q: What network aired Mad Men?
A: AMC.
Q: Who created it?
A: Matthew Weiner.
Q: How many seasons does it have?
A: Seven.
Q: What profession gives the series its title?
A: “Mad men” was used in the show as a nickname for Madison Avenue advertising men.
Q: What does Madison Avenue symbolize?
A: New York advertising industry.
Q: Why is Mad Men especially deep trivia material?
A: Ad pitches, office hierarchies, affairs, secret identities, fashion, historical events, products, and subtle character changes all matter.
How Did You Score?
If Dick Whitman, Belle Jolie, the Carousel, SCDP, Jaguar, Lane's forgery, Learjet, and the Coke implication all came easily, your Mad Men trivia knows how to sell the feeling.
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