Riddles With Answers

What fashion designer directed an Oscar-nominated feature film?

Ralph Lauren
Tom Ford
Donna Karan
Vera Wang

Fact: Tom Ford is a fashion designer and filmmaker. He launched his luxury brand in 2006, having previously served as the creative director at Gucci and Yves Saint Laurent. In March 2005, Ford announced the launch of his film production company, Fade to Black. Ford directed the films A Single Man (2009) and Nocturnal Animals (2016), both films were Oscar-nominated. His directorial debut A Single Man is based on the novel of the same name by Christopher Isherwood. The film starred Colin Firth who was nominated for an Academy Award.

Correct Answer: Tom Ford

Which U.S. river is widely known for flowing backward?

Chicago River
Hudson River
Colorado River
Mississippi River

Fact: The Chicago River is renowned for flowing “backwards” after a landmark engineering project completed in 1900 reversed its natural direction. Originally draining into Lake Michigan, the river was redirected away from the lake through the Chicago Sanitary and Ship Canal to protect the city’s drinking water from sewage contamination. The reversed flow now carries water toward the Des Plaines River and ultimately into the Mississippi River system, making the Chicago River the most famous example of an intentionally reversed river in U.S. history.

Correct Answer: Chicago River

What is the highest military rank in U.S. history that has been held by only three individuals?

General of the Army
Five-Star General
General of the Armies
Supreme Allied Commander

Fact: The rank of General of the Armies is the highest possible military rank and has been conferred only three times in U.S. history. John J. Pershing first received the title in 1919 for his leadership during World War I. George Washington was posthumously promoted to the rank in 1976 to ensure he would forever remain the nation’s most senior military officer. Ulysses S. Grant was posthumously granted the rank in 2022, recognizing his role as the Union’s top commander during the Civil War. Unlike the five-star rank of “General of the Army,” the designation “General of the Armies” stands above all others.

Correct Answer: General of the Armies

Which of these animals has a tail?

Aardvark
Capybara
Guinea pig
Manx cat

Fact: An aardvark does have a tail, and it is a thick, muscular, and clearly visible extension of the body that helps with balance and stability while the aardvark is digging and moving through burrows. The tail often drags behind the aardvark as it walks and can help brace the body when backing into or turning within tunnels. In contrast, the capybara and the guinea pig are commonly classified as tailless mammals. The Manx cat is also tailless, the result of a naturally occurring genetic mutation which has become a defining characteristic of the breed.

Correct Answer: Aardvark

What specific time is displayed on device screens in Apple advertisements?

8:46
9:41
3:21
11:17

Fact: The time 9:41 appears on the screens of devices in nearly every advertisement for Apple products. The detail dates back to the original iPhone unveiling in 2007, when Steve Jobs introduced the device roughly 41 minutes into the keynote presentation. Apple intentionally matched the on-screen clock to the real-time moment of the reveal, turning a precise logistical choice into a subtle yet recognizable branding signature. Although some early marketing materials briefly displayed 9:42, Apple ultimately standardized on 9:41 across its product marketing imagery.

Correct Answer: 9:41

Which writer famously wrote the line, “All that glisters is not gold”?

Mark Twain
Geoffrey Chaucer
Charles Dickens
William Shakespeare

Fact: The phrase “All that glisters is not gold” appears in The Merchant of Venice, written by William Shakespeare. In the play, the line is used to caution characters against being misled by appearances, emphasizing that something attractive or impressive on the surface may lack true value beneath. Over time, the wording evolved into the more familiar modern version, “All that glitters is not gold.” The expression has endured for centuries, becoming a widely used proverb in literature, politics, and everyday speech as a reminder to look beyond surface impressions when judging people, ideas, or situations.

Correct Answer: William Shakespeare

Which song made history as the very first No. 1 on the Billboard Hot 100?

“Peggy Sue” by Buddy Holly
“Jailhouse Rock” by Elvis Presley
“Bird Dog” by The Everly Brothers
“Poor Little Fool” by Ricky Nelson

Fact: When the Billboard Hot 100 debuted on August 4, 1958, it marked a major turning point in how popular music success was measured in the United States. Prior to its creation, Billboard maintained several separate charts that tracked sales, radio airplay, and jukebox popularity independently. The Hot 100 unified these metrics into a single, comprehensive ranking designed to reflect a song’s overall commercial and cultural impact. The very first song to top this new chart was “Poor Little Fool” by Ricky Nelson, making it the inaugural No. 1 hit in Hot 100 history.

Correct Answer: “Poor Little Fool” by Ricky Nelson

Which NFL player is the namesake of the league’s annual humanitarian award?

Frank Gifford
Walter Payton
Johnny Unitas
Roger Staubach

Fact: The NFL’s most prestigious humanitarian honor is officially known as the Walter Payton NFL Man of the Year Award. Renamed in Payton’s honor in 1999, the award recognizes players who demonstrate outstanding community service, philanthropy, and leadership off the field, in addition to excellence in football. Nicknamed “Sweetness,” Payton was revered not only as one of the greatest running backs in NFL history, but also for his lifelong commitment to charitable causes, making him a fitting symbol of the league’s highest off-field distinction.

Correct Answer: Walter Payton

What cartoon was the inspiration for the 1981 arcade hit Donkey Kong?

Popeye
Yogi Bear
Mighty Mouse
Scooby-Doo

Fact: Before becoming one of the most popular video games of all time, Donkey Kong began as a very different project. Nintendo originally sought to create an arcade game based on the popular cartoon sailor Popeye, with Popeye rescuing Olive Oyl from Bluto. When the licensing deal fell through, designer Shigeru Miyamoto reworked the concept and replaced Popeye with Jumpman (later known as Mario), Bluto with a giant ape, and Olive Oyl with Pauline. The gameplay mechanics remained, but the characters changed, giving rise to Donkey Kong, launching both Mario and Nintendo into video game history.

Correct Answer: Popeye

The Supreme Court case Bush v. Gore centered on an electoral recount in which state?

Ohio
Wisconsin
Florida
Pennsylvania

Fact: The landmark 2000 Supreme Court decision Bush v. Gore arose from an close presidential election between George W. Bush and Al Gore, with the outcome hinging on contested vote counts in Florida. Confusion over ballot designs, inconsistent recount standards, and razor-thin margins led to multiple recounts and legal challenges. The Supreme Court ultimately halted the statewide recount, awarding Florida’s decisive electoral votes and the presidency to George Bush. The case remains one of the most controversial rulings in American political history.

Correct Answer: Florida