u/TheLostPariah

$200 - John Dillinger left his fingerprints across the Midwest, and so did this 2009 biopic about him >!What is Public Enemies?!<

$400 - While primarily based in Chicago, this 1980 classic about a “mission from God” staged its ‘Nazi Jump’ scene on the then-unfinished Interstate 794 >!What is Blues Brothers!<

$600 - Flyovers of the Cream City set the scene for this pre-wedding Kristen Wiig comedy >!What is Bridesmaids?!<

$800 - The Milwaukee Brewers’ County Stadium was prominently featured in Major League, which fictionalizes this other Midwestern MLB team >!Who are the Cleveland Indians (Guardians)?!<

$1000 - The Milwaukee Art Museum’s 2001 addition, designed by this Spaniard, stood in for a villain’s lair in ‘Transformers: Dark of the Moon’ >!Who is Santiago Calatrava?!<

$200 - Rapper A$AP Rocky says his hip-hop collective’s name stands for “Always Strive and Prosper,” instead of this more common expedient request >!What is As Soon As Possible?!<

$400 - Perry the Platypus is a secret spy for OWCA, the Organization Without a Cool Acronym, in this Disney Channel cartoon >!What is Phineas & Ferb!<

$600 - POS often stands for “Piece of Some-fecal-matter” or this synonym for a checkout point >!What is Point Of Sale?!<

$800 - The successor to Greenwich Mean Time, Coordinated Universal Time is known by this out-of-order acronym >!What is UTC?!<

$1,000 - A 1917 letter to Winston Churchill includes the first known usage of this three-letter invocation of a higher power >!What is OMG?!<

Musicians’ claimed side gigs
$200 - John Denver, Pete Seeger and Johnny Cash sang of working on one of these means of transportation, all the live long day >!What is a railroad?!<
$400 - The Hollies were downtown working for this agency when they encountered a long cool woman in a black dress >!What is the FBI?!<
$600 - Dolly Parton says she worked one of these shifts in her 1981 Grammy winner >!What is a 9 to 5?!<
$800 - Rose Royce never actually operated one of these hygienic businesses, despite the implication of their most iconic funk hit, yeah >!What is a Car Wash?!<
$1000 - Tommy Shaw of Styx dreams of becoming one of these while waiting in a welfare line >!What is a Blue Collar Man?!<

Musicians’ actual side gigs
$400 - His students in Northumberland probably knew him as Mr. Sumner >!Who is Sting?!<
$800 - You could’ve ordered a coffee Hot To Go from this barista-turned-pop sensation >!Who is Chappell Roan?!<
$1200 - Producer Suge Knight appeared in two NFL games for this team during the 1987 players’ strike >!Who are the Philadelphia Eagles?!<
$1600 - Before becoming one of the biggest rap stars of his day, this Brooklynite was a counselor at Jewish summer camp as a teen >!Who is Notorious B.I.G. (Also accepted, Biggie Smalls and Christopher George Latore Wallace)!<
$2000 - This British physicist and science educator previously was the keyboardist for the rock group Dare >!Who is Brian Cox?!<

$200 - This 76er never went to medical school >!Who is Dr. J (also accepted Julius Erving)!<
$400 - He was Elvis Presley’s longtime manager, and he actually did serve in the U.S. military for a time >!Who is Col. Tom Parker?!<
$600 - Stevie Wonder gave this Jazz great the title of “Sir” in a 1977 hit >!Who is Duke Ellington?!<
$800 - This 18th century sailor who landed in Australia and died in Hawaii never actually held the rank he is most remembered by >!Who is Captain James Cook?!<
$1000 - Joshua Michael Tillman ain’t no priest, but as an indie rocker he is better known by this stagename >!Who is Father John Misty?!<

$200 - Peter Falk won four Emmys for his portrayal of the title detective in this NBC procedural, or one of Sri Lanka’s two capitals >!What is Columbo | Colombo?!<

$400 - Pick up a pastrami sandwich and some coleslaw here, or India’s most populous megacity >!What is deli | Delhi?!<

$600 - Slang for very good-looking, or a Montana city-county >!What is beaut, Butte?!<

$800 - Your mother’s daughter’s son’s sister, or a coastal French city >!What is niece | Nice!<

$1000 - Very bloody, or the Georgian village where Josef Stalin was born >!What is gory | Gori?!<

$200 - Prior to the advent of videoconferencing, being served this type of summons legally obligated you to appear in court in person >!What is a subpoena?!<

$400 - During one of these mid-inning baseball gatherings, you’ll find coaches and catchers strategizing with a pitcher >!What is a mound visit?!<

$600 - Wits like Harpo Marx and Alexander Woollcott exchanged ideas at a “round table” in New York City hotel, named for a First Nations people >!What is the Algonquin Hotel!<

$800 - Catholic historian John W. O’Malley argued this 1155-day 20th century gathering involving 2,625 people was the largest meeting of all time >!What is Vatican II (also accepted, the Second Vatican Council)!<

$1000 - Stalin, FDR and Churchill met face-to-face only twice during the Second World War, once in Tehran, and again in this Soviet resort town >!What is Yalta?!<

$400 - Nora Ephron wrote the screenplay for this biopic featuring two chefs whose given names are one vowel apart >!What is Julie & Julia!<

$800 - These Greater and Lesser Biblical apostles may have been brothers >!Who are James the Greater and James the Lesser?!<

$1200 - John Flansburgh and John Linnell are the founding members of this alt-rock group known for its cover of “Istanbul (Not Constantinople)” >!Who are They Might Be Giants?!<

$1600 - Two English queens regent were named Elizabeth, and two others share this name >!What is Mary?!<

$2000 - Drag queen podcasters Trixie & Katya share this birth name >!Who are Brian and Brian?!<

$200 - Señor Aflame >!Who is Mr. Burns!<
$400 - Belgium’s Dutch-speaking northern region >!What is Flanders?!<
$600 - Shortform graphic novel fella >!Who is Comic Book Guy!<
$800 - Legless lizard guy who is arrested a lot >!Who is Snake Jailbird?!<
$1000 - Secondary attraction Short women’s haircut popularized in the early 1900s by flappers >!Who is Sideshow Bob?!<

$200 This is the only of the 13 Colonies that is not a birthplace of any U.S. presidents or vice presidents >!What is Rhode Island?!<

$400 Peregrine falcons can be found on all continents, except this one >!What is Antarctica?!<

$600 This nation is the only one in Asia to share its country name with its capital city >!What is Singapore?!<

$800 No Major League Baseball teams have ever called this New York City borough home >!What is Staten Island?!<

$1000 He was the only Gibb brother not in the Bee Gees >!Who is Andy Gibb?!<

Don’t say this word. It is forbidden, prohibited, filthy and uncouth >!What is taboo?!<

Many call it The Big Island, so as to not confuse it with the name of a state >!What is Hawai’i?!<

An Australian toy was the inspiration for this 1950s plastic fad, not a Hawaiian dance >!What is a Hula hoop?!<

This is the thing to say on a bright Hawaiian Christmas Day >!What is Mele Kalikimaka?!<

The world’s largest collaborative -pedia gets its name from this Hawaiian word meaning “quick” >!What is wiki!<

From my layman's knowledge, I've heard that couples therapy especially is focused around "I" statements and never "You." But, how do you figure it when it truly is a "You" problem.