Doug van Gundy was one of the three most famous contestants during the August primetime series, winning $250,000. Also, on his $100 question, he asked the audience and got it right despite the question being ambiguous. When the first appearance of Doug ended, the Ask the Audience was reinstated for Doug and he continued on to win $250,000 in the end.

Fastest Finger First Question Edit

Fastest Finger First
Put the following Winter Olympic host cities in order from most recent to earliest.
• A: Innsbruck • B: Liliehammer
• C: Nagano • D: Albertville

Out of the remaining 9 contestants, Doug got it right in the fastest time, who answered C-B-D-A (in a time of 4.33 seconds), making it into the Hot Seat.

Doug's Run to the Million Edit

$100 (1 of 15) - Not Timed
What mode of transportation was once nicknamed the "Iron Horse"?
'Ask the Audience' lifeline used
• A: Motorcycle - 8% • B: Locomotive - 77%
• C: Mechanized Plow - 8% • D: Automobile - 7%
After Part 1 of Doug van Gundy's runthrough ended, it turned out that when Doug referred to a magazine called, "Iron Horse", one of the answers, A: Motorcycle, was correct, too. So, the Ask the Audience lifeline was reinstated the next show.

$200 (2 of 15) - Not Timed
Which of the following is not a comic book hero?
• A: The Human Torch • B: Green Lantern
• C: Spider-Man • D: Underpants Man

$300 (3 of 15) - Not Timed
Tony the Tiger is the trademarked character for what brand of breakfast cereal?
• A: Apple Jacks • B: Frosted Flakes
• C: Frosted Mini-Wheats • D: Corn Flakes

$500 (4 of 15) - Not Timed
Who founded Playboy magazine?
• A: Hugh Hefner • B: Bob Guccione
• C: Larry Flynt • D: Hugh Grant

$1,000 (5 of 15) - Not Timed
In what state was former president Jimmy Carter born and raised?
• A: Georgia • B: Alabama
• C: South Carolina • D: Tennessee

$2,000 (6 of 15) - Not Timed
What is another name for a human being's lower jawbone?
• A: Cranium • B: Ulna
• C: Macsilla • D: Mandible

$4,000 (7 of 15) - Not Timed
What rock star was born Gordon Sumner?
• A: Sting • B: Flea
• C: Donovan • D: Marky Mark

$8,000 (8 of 15) - Not Timed
Which of the following is the nearest translation to the French fashion term "pret-a-porter"?
• A: Height of Fashion • B: Out of Fashion
• C: Ready to Wear • D: Easy to Wash

$16,000 (9 of 15) - Not Timed
What object is the man holding in the famous painting "American Gothic"?
• A: Axe • B: Pitchfork
• C: Saddle • D: Scythe

$32,000 (10 of 15) - Not Timed
What is the name of the coffee shop in the television series "Friends"?
• A: Christine's Latte • B: Java Man
• C: Perk Square • D: Central Perk

$64,000 (11 of 15) - Not Timed
Which American poet wrote "The Road Not Taken"?
• A: Robert Frost • B: Ezra Pound
• C: T.S. Eliot • D: Carl Sandburg

$125,000 (12 of 15) - Not Timed
On November 22, 1963, where was Lee Harvey Oswald arrested?
'Ask the Audience' lifeline used
• A: Department Store - 2% • B: Movie Theater - 85%
• C: Book Depository - 8% • D: Drugstore - 5%

$250,000 (13 of 15) - Not Timed
Since 1973, the annual Iditarod dogsled race has started in Anchorage and ended where?
'50:50' and 'Phone a Friend' lifelines used
• A: Juneau • B: Nome
• C: Barrow • D: Fairbanks
Doug used his Phone a Friend, after 50:50, to call Russ, a dog owner. He said the answer was B: Nome and he was absolutely positive. Doug went with B: Nome and won the most memorable $250,000 ever.

$500,000 (14 of 15) - Not Timed
Which English king does William Shakespeare refer to as "Bolingbroke"?
• A: Richard III • B: Henry IV
• C: Henry V • D: Henry VIII
After reading the question and four answers, Doug exclaimed that he wants to give someone else a chance to play, so he took the quarter-million dollars and went. The answer was B: Henry IV.