Jon Jack and his brother Jay weren't the only ones perplexed by the cryptic and in some cases, comical questions.
Several of the 22 teams knew Winston Churchill coined the phrase, "Iron Curtain." Few knew Charlie Brown acquired Snoopy from the Daisy Hill Puppy Farm. No one realized Kellogg's Frosted Flakes is America's best-selling cereal.
"These questions are a little bit upscale. Either that or we're really stupid," said Diana McKinley of Falling Waters, an education specialist with Project Head Start and one of a six-member team of trivia whiz wannabes.
But all came in the spirit of friendly competition: Jay Jack's 4-year-old daughter, Jassmine, promised her father and uncle would be grounded until September if they didn't win her a trophy.
McKinley's team wore goofy hats and brought good luck charms.
"The only thing it may get us is a prize for the most vivid outfits, but we have more fun than anybody," McKinley said.
The game was the brainchild of Therese Hess, Literacy Volunteers board member, who was trying to come up with a fund-raiser and heard about the trivia game through a friend in Wisconsin.
Other board members pored over magazines, encyclopedias, newspapers, the Bible and trivia books to formulate the 25 questions for each of four rounds.
About 130 people participated, divided into 22 teams.
Hess admitted the questions were probably too tough. This year's winners, employees of The Journal, won with only 60 correct questions out of 100.
Next year Hess hopes to create three different playing levels so beginners and experts can compete against others in their class.
Prizes were donated by local businesses, including the grand prize of six tickets to any show at the Old Opera House in Charles Town, W.Va.
The grand prize winners also received a trophy. They must play again next year and win if they want to keep it. If not, next year's champions will take it home.
Second-place winners received tickets to a play at the Apollo Civic Theatre in Martinsburg. Members of the third-place team won lunches at the Boomtown Inn.
Joe McCabe, captain of the second-place winners, said next year he plans to win.
"We had a good time and we got better and better as the rounds went on," McCabe said. "A lot gets stuck in these old brains over the years."