Jeopardy! celebrates the show’s 60th anniversary in 2024. It’s a show that many generations, including Baby Boomers, have grown up with. We’re celebrating 60 years of Jeopardy with the most difficult real Jeopardy! questions about Baby Boomers or that Baby Boomers are more likely to be able to answer due to the people or historical events.
When Jeopardy! started, it was hosted by Art Fleming, an actor known for “International Detective” and NBC’s “The Californians.” Merv Griffin spotted his work and invited him to audition for a daytime game show he was working on. Fleming did well and became the show’s weekly host from 1964 to 1975.
The show tried a nighttime syndicated version from 1974 to 1975 and then took a break until 1978 when it returned as a daily game show. It would go on one more hiatus until 1984. That’s when Fleming’s friend Alex Trebek took over the reins until he died in 2021.
Throughout the years, “Jeopardy” has been nominated or won several awards per IMBD and Jeopardy! Here’s a summary of wins during both Fleming’s years as host and Trebek’s.
- 1 Critics’ Choice Real TV Awards
- 1 Media Access Award
- 1 Peabody Award
- 1 Writer’s Guild of America Award
- 1 Young Artist Award
- 12 Online Film & Television Association Awards
- 44 Emmy Awards
See how many of the following difficult real Jeopardy! questions you can answer from the questions below. I’m Gen X and found some to be much easier than others. Question difficulty is based on the value of the question as shown on the board. If you’re like me and love trivia games, I have another. See how many of the questions you can correctly answer on “Test Your Knowledge with These 15 Harry Potter Trivia Questions.”
FAMOUS DOCTORS $400
Answer
Dr. Spock
BABY BOOMER SOONER $1200
Answer
Elizabeth Warren
BABY BOOMER MEMORIES $1200
Answer
A communist sympathizer
FAMOUS DOGS $500
Answer
“Here’s Boomer”
BABY BOOMER SOONER $1600
Answer
Tulsa
“E”-MALE $1200
Answer
Boomer Esiason
ABBREV. TV $2000
Answer
Captain Kangaroo
CONFERENCE CHAMPIONSHIP HEROES $1000
Answer
Johnny Unitas
BRIAN THE BABY BOOMER $500
Answer
Golf
BABY BOOMER MEMORIES $1600
Answer
Old Yeller
OK BOOMER $1200
Answer
WASHINGTON, DC - OCTOBER 07: United States Supreme Court Associate Justice Clarence Thomas poses for an official portrait at the East Conference Room of the Supreme Court building on October 7, 2022 in Washington, DC. The Supreme Court has begun a new term after Associate Justice Ketanji Brown Jackson was officially added to the bench in September. (Photo by Alex Wong/Getty Images)
Clarence Thomas
BABY BOOMER MEMORIES $2000
Answer
Jann Wenner
FUNNY TV SONGS $1200
Answer
Community
AMERICAN LITERATURE
Answer
Sperm Whale (Physeter macrocephalus), Caribbean Sea, Dominica
Moby Dick
OK BOOMER $2000
Answer
The Vietnam Veterans of America
BABY BOOMER SOONER $2000
Answer
The Seattle Seahawks