Music
History
Culture
Slang
Technology
100
1964: This band from Liverpool, England first came to the United States and performed on the Ed Sullivan Show to over 70 million viewers.
Who are the Beatles?
100
1963: He was the 35th president of the United States until his term was cut short.
Who is John F. Kennedy?
100
1960s: This group of people were part of the counterculture movement that started in the United States in the mid 1960s; they were most associated with Greenwich Village in New York City and Haight-Ashbury in San Francisco.
What are hippies?
100
Two syllables: If someone calls you this word, they must think you're pretty cool.
What is groovy?
100
1963: This piece of 60s décor has something in common with volcanos. 
What is a lava lamp?
200
1968: This singer shocked the world when she left The Supremes to pursue a solo career.
Who is Diana Ross?
200
1954-1968: This nonviolent social movement sought to end racial segregation, discrimination, and disenfranchisement throughout the United States.
What is the Civil Rights Movement?
200
1961: He is an artist known for his contributions to the "pop art" movement. His most famous piece is of a soup can.
Who is Andy Warhol?
200
Two syllables: You would call any disappointing situation--like the rain at Woodstock--this word.
What is a bummer?
200
1969: He was the first man to walk on the moon.
Who is Neil Armstrong?
300
1969: This music festival was held in upstate New York, and included acts such as Jimi Hendrix, Sly & The Family Stone, Grateful Dead, and The Who.
What is Woodstock?
300
1965: The United States officially became involved in this war, to many citizens' extreme disapproval.
What is the Vietnam War?
300
1964: This famous boxer changed his name from ____ to Muhammed Ali.
Who is Cassius Clay?
300
Two syllables: This word is used to describe people you find attractive, not the furry animal.
What is foxy?
300
1965: This popular board game makes a game out of avoiding medical malpractice.
What is Operation? 
400
1965: This singer-songwriter struck controversy and faced boos from the crowds when he "went electric" at the Newport Folk Festival.
Who is Bob Dylan?
400
1967: He was the first African-American Supreme Court Justice.
Who is Thurgood Marshall?
400
1960: Alfred Hitchcock directed and produced this film, famous for its terrifying shower scene.
What is Psycho?
400
One syllable: This word, possibly referring to their haircuts, is code for the police.
What is the fuzz?
400
1963: This invention from Philips helped the world listen to music on the go.
What is the cassette tape?
500
1968: This musical, featuring songs such as 'Aquarius' and 'Good Morning Starshine' opened on Broadway and ran for 1750 performances.
What is Hair?
500
1962: This event in Cuba involved a stand-off between the United States and the Soviet Union that nearly ended in nuclear war.
What is the Cuban Missile Crisis?
500
1962: This bombshell famously sang Happy Birthday to the president (not sure Jackie was too pleased about it, either).
Who is Marilyn Monroe?
500
Two words (and two syllables): This car:
What is a slug bug?
(or punch bug)
500
1964: This company invented the first VCR home video recorder.
What is Sony?