Michael is a host of The Daily Show and author of “Lucky Loser.” Wendi is the star of St. Denis Medical. Wendi’s charity is WriteGirl. Michael’s charity is ALS San Diego.
$100
In which classic game do you win by bankrupting all of the other players?
A: Clue B: Monopoly
C: Battleship D: Candy Landlords
Answer
B: Monopoly
Kids commonly use toilet paper, and lots of it, when dressing as what character for Halloween?
A: Vampire B: Werewolf
C: Mummy D: Ogre
Answer
C: Mummy
Which variety of soup typically contains noodles in 26 different shapes?
A: Clam chowder B: Split pea
C: Alphabet soup D: Cream of mushroom
Answer
C: Alphabet soup
“Your eyes can get sunburned” is a fact mentioned in a 2026 health article titled “4 Things” what doctors “Wish You Knew About Your Eyes”?
A: Dermatologists B: Cardiologists
C: Podiatrists D: Ophthalmologists
Answer
D: Ophthalmologists
Alaska is the only U.S. state where you can see which of these animals in the wild?
A: Grizzly bears B: Pandas
C: Polar bears D: Koalas
Answer
C: Polar bears
As you might guess from its name, what English soccer club has the legendary Robin Hood as its mascot?
A: Manchester United B: Nottingham Forest
C: Liverpool D: Crystal Palace
Answer
B: Nottingham Forest
Before gaining fame as the drummer for the Roots, Ahmir Thompson adopted a stage name inspired, in part, by what hip-hop group?
A: A Tribe Called Quest B: Public Enemy
C: Wu-Tang Clan D: De La Soul
ATH
Jimmy says Ahmir is known as ?uestlove, based on A Tribe Called Quest.
Answer
A: A Tribe Called Quest
$8,000
How many pennies would you need to total exactly $1,000,000?
A: Ten million B: One hundred million
C: One billion D: Ten billion
Answer
B: One hundred million
Commemorating an important 1965 event in the Civil Rights movement, which of these cities hosts an annual Bridge Crossing Jubilee?
A: Little Rock, Arkansas B: Jackson, Mississippi
C: Selma, Alabama D: Greensboro, North Carolina
Answer
C: Selma, Alabama
$32,000
Let’s make fetch happen: start a film title with “Fe” and end it with “tch” and you have a 2005 romcom starring Drew Barrymore and what costar?
A: Adam Sandler B: Jimmy Fallon
C: Hugh Grant D: Justin Long
ATA
Michael remembers Adam was in Fifty First Dates, so he’s not it. Jimmy was in a movie about baseball, but they don’t know the name.
A: 14% B: 47% C: 21% D: 18%.
A: 14% B: 47% C: 21% D: 18%.
Answer
B: Jimmy Fallon (Fever Pitch)
$64,000
In 2014, chess master Garry Kasparov became a citizen of what country whose flag, coincidentally, features a checkerboard pattern?
A: Albania B: Greece
C: Croatia D: Serbia
50:50
When Michael watches tennis on TV, they show the players’ countries’ flags, and he thinks Croatia’s is a checkerboard.
50:50 leaves C & D.
50:50 leaves C & D.
Answer
C: Croatia
In the midst of a 12-week chart-topping run on the Billboard Hot 100, which song was both the last #1 of the 1900s and the first #1 of the 2000s?
A: Lose Yourself B: MMMBop
C: Bootylicious D: Smooth
Michael says Lose Yourself was around 2004. Wendi believes it’s Smooth (though neither of them thinks that song deserves to have been #1 for so long).
Answer
D: Smooth
$250,000
According to his authorized biography, Steve Jobs would sometimes do what with toilet bowl water at Apple’s offices?
A: Soak his feet B: Ferment kombucha
C: Wash his armpits D: Fill water pistols to spray at employees
PAF
Michael’s friend is Aaron Stark, a lawyer and Marine. Aaron thanks Jimmy for defending the First Amendment. Time runs out without Aaron answering. They consider walking away, then go with D.
Answer
A: Soak his feet
Michael and Wendi win $32,000 for their charities.
Michael and Wendi win $32,000 for their charities.