Grab a glass of old-fashioned, kick off your wingtips, and settle into your mid-century modern chair, because we’ve got a quiz for you that’s straight out of the ‘Mad Men’ era. We promise it’s more fun than a three-martini lunch and safer than riding a lawnmower through the office. So light up a Lucky Strike (figuratively, of course), and prepare to step back into the world of Sterling Cooper & Partners. But remember, if Don Draper can keep all his secrets straight, you can certainly tackle these trivia questions. So, let’s get started, shall we?
1. What is the name of the advertising agency where Don Draper works at the beginning of the series?
2. In which city is Mad Men set?
3. Who was the first actor cast for the series?
4. Which character’s real name is Dick Whitman?
5. What is the most expensive outfit worn in the series?
6. What’s the name of Don’s first wife?
7. Who is the youngest character to become a copywriter at Sterling Cooper?
8. What is Don Draper’s favorite cocktail?
9. Who loses their foot to a lawnmower in the office?
10. Which character gets divorced the most times?
11. Who plays the character of Peggy Olson?
12. What is the name of the cigarette account that Sterling Cooper Draper Pryce loses in the beginning of season 4?
13. What’s the name of the second advertising agency formed by Don Draper and his colleagues?
14. What is the real name of Joan’s husband who goes by the nickname “Dr. Rape”?
15. How many times did Jon Hamm audition for the role of Don Draper?
16. What piece of pop culture does Don use in his famous Kodak pitch?
17. What is the name of Sally Draper’s teacher with whom Don has an affair?
18. Which is the first major account Peggy lands on her own?
19. What is the name of the law firm that represents Megan in her divorce from Don?
20. Who’s the biggest client Sterling Cooper has at the beginning of the series?
21. Who directed the Mad Men pilot?
22. Which Mad Men actor also made appearances on The Sopranos?
23. What’s the name of the man with whom Betty has an affair in season 2?
24. Which department store does Rachel Menken own?
25. What is the title of the first episode?
26. Who is the first person at Sterling Cooper Draper Pryce to learn about Don’s true identity?
27. How many times did Mad Men win the Emmy for Outstanding Drama Series?
28. In what year does the series start?
29. Who is the oldest major character in the series?
30. What is Joan’s maiden name?
31. Who did Peggy give birth to at the end of season 1?
32. Who designed the costumes for the series?
33. What is Roger Sterling’s middle name?
34. Who does Lane Pryce have a romantic relationship with in Season 5?
35. What’s the name of the bar that Don frequents throughout the series?
36. What is the real name of the actress who plays Sally Draper?
37. Who was the last main character to be cast?
38. Which character unexpectedly dies in the office?
39. How many children do Don and Betty have together?
40. Who did Don Draper impersonate to start a new life?
41. What object does Pete Campbell purchase that leads to an argument with his wife, Trudy?
42. What is the name of the French-Canadian nurse who briefly dates Don Draper?
43. Which actor portrays the character Salvatore Romano?
44. What notable change did Peggy Olson make to the traditional Popsicle advertising?
45. Who does Roger Sterling marry in the series?
46. What war did Don Draper serve in?
47. What song does Bert Cooper sing in Don’s hallucination?
48. What book does Don Draper read in the Season 6 premiere?
49. Who is the founder of Sterling Cooper?
50. What does Peggy Olson purchase to assert her independence?
51. Which character is discovered to be secretly writing a play?
52. What is the real name of the character Betty Francis?
53. What does Don Draper give Megan as a gift that significantly upsets her?
54. Which historical event is featured in the Season 3 finale?
55. Who becomes the new head of Accounts after Pete Campbell is promoted?
56. Which company does Peggy Olson leave Sterling Cooper Draper Pryce for?
57. Who played the role of Megan Draper?
58. How does Ida Blankenship, Sterling Cooper’s elderly secretary, die?
59. In which city does Don propose to Megan?
60. What causes Pete Campbell to challenge Bob Benson to a fight?
61. Who is Joan Holloway’s baby’s father?
62. What is the name of the character portrayed by Vincent Kartheiser?
63. Who is Peggy Olson’s first mentor at Sterling Cooper?
64. In season 4, which Beatles album does Megan introduce to Don?
65. Which character is an art director and is secretly gay?
66. What significant event in Sally’s life does Betty miss because she is on a vacation in Italy?
67. Which account does Peggy land that makes her the first female copywriter to bring in business?
68. What type of business does Trudy’s father own?
69. Who does Joan consider her best friend at the office?
70. What is the full name of the character known as Duck?
71. Who is the father of Peggy Olson’s baby?
72. What does Don Draper ask Peggy to do after he bails her out of jail?
73. Which character stows away on Pete Campbell’s train to Connecticut to avoid the Vietnam draft?
74. Which song does Megan sing to Don at his surprise birthday party?
75. Which historical event occurs during Sally’s school trip to the planetarium?
76. Which brand does Don pitch a commercial to featuring children playing in the snow?
77. Who accidentally shoots Ken Cosgrove during a hunting trip?
78. What does Bert Cooper remove when he enters his office?
79. Who was the actor who played Lane Pryce?
80. In the series finale, where does Don Draper end up?
81. Who punches Pete in the face in the office?
82. What is the name of the brothel where Don Draper grew up?
83. What alias does Don Draper use when he’s trying to be incognito?
84. Who does Peggy Olson live with when she first moves to Manhattan?
85. Which Sterling Cooper employee joins the Hare Krishnas?
86. Who does Betty Draper marry after divorcing Don?
87. What was the name of Joan’s husband?
88. Who does Roger Sterling take LSD with?
89. What is the name of Don’s brother who takes his own life?
90. Which character comes out as gay to his wife after a failed attempt to seduce a male colleague?
91. Who is Sally Draper’s therapist?
92. In the pilot, what major client does Don have to prepare a new advertising campaign for?
93. Which major character does not make it to the end of the series, passing away in season 7?
94. What sport does Don Draper take up in season 2 to combat his increasing alcoholism?
95. What book does Don read that leads him to propose to Megan?
96. What job does Joan take on after she leaves Sterling Cooper Draper Pryce?
97. Who says the final line of dialogue in the series?
98. What type of cancer is Betty diagnosed with in the final season?
99. What song does Don Draper listen to in the final scene of the series?
100. Who does Peggy end up with in the series finale?
101. What was the name of the fictional soap opera that Megan Draper was a star of?
102. What is the name of the rival advertising agency led by Duck Phillips?
103. Who replaces Don Draper as Creative Director while he is on leave?
104. Who becomes the head of the television department at Sterling Cooper Draper Pryce?
105. Who does Roger Sterling write a memoir for in season 4?
106. What is the name of the first African American secretary at Sterling Cooper Draper Pryce?
107. What name does Peggy consider using for her new agency with Joan?
108. What is the name of the department store heiress who has a brief affair with Don Draper?
109. Who was the client that ends up firing Sterling Cooper Draper Pryce in season 4?
110. What name does Peggy use when she checks into a hotel with Duck Phillips?
111. What is the name of the daughter of Roger Sterling and Joan Harris?
112. Who is the first person at Sterling Cooper Draper Pryce to learn about Don’s secret past?
113. What animal does Roger compare Bert Cooper’s Japanese clients to?
114. What major event does Sterling Cooper Draper Pryce throw a party for in season 5?
115. Who does Don visit in California that causes him to reconsider his life in advertising?
116. Who does Pete Campbell have an affair with in the suburbs?
117. What was Peggy’s final position at Sterling Cooper Draper Pryce?
118. Who does Roger Sterling marry in the first season?
119. Who convinces Don to sign a no-compete clause with Sterling Cooper Draper Pryce?
120. What does Sally Draper catch Don doing with Sylvia Rosen in season 6?
121. What’s the name of the waitress Don becomes obsessed with in season 7?
122. Which character’s actor also directed five episodes of the show?
123. Which iconic artist’s work is featured prominently in Bert Cooper’s office?
124. Who buys Sterling Cooper & Partners, making millionaires of the partners?
125. What Broadway musical’s cast album does Don give to Sally and Bobby?
126. Who writes a controversial article about the cigarette industry in The New York Times?
127. What does Roger Sterling wear to the office after taking LSD?
128. What is the name of the computer system installed at Sterling Cooper & Partners?
129. What gift does Peggy give to Don when she leaves Sterling Cooper Draper Pryce?
130. Who does Joan have a baby with?
131. Who did Peggy Olson replace as Don Draper’s secretary?
132. What is the name of Don’s wife in the final season?
133. Who fires Jaguar to make way for a potentially bigger account?
134. Who does Peggy Olsen date in season 5?
135. What major historical event does the show end with?
136. What is the name of the French Canadian secretary that Roger Sterling marries?
137. Who is the real-life daughter of Roger Sterling’s actor, John Slattery?
Well, wasn’t that a trip down Madison Avenue? Whether you were the top dog like Don Draper or feeling a bit more like a Peggy on her first day, we hope you enjoyed this journey back to the 1960s. Thanks for joining us for this blast from the past, and don’t forget to check out the other quizzes on Trivia Bliss, including one all about The Sopranos. We have a wide variety of topics to test your knowledge on. Until next time, stay curious and keep quizzing!
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