Boffo, US slang meaning “very good”. It originated from the film trade magazine, Variety.
Note that Paris is wearing one of the 400 campaign buttons that Lorelai made for them, showing Rory’s and Paris’ faces, against what looks like the US flag (as if it’s a real presidential election, not just one for school).
Bush League is American slang for something which is of an inferior standard; unsophisticated, unprofessional, mediocre.
The slang comes from baseball, where the small-town teams below the minor league became informally known as the “bush league”, because of their rural origins, and because they often played on rough fields bordered by bushes. The slang dates to the very early twentieth century.
Note that the role of the repellent Zach is portrayed by Seth MacFarlane, who Daniel Palladino (the writer of this episode) worked with on his animated television sitcom, Family Guy.
The “boondocks” or the “boonies” is American slang for a distant or remote rural location, especially one with few amenities. “Boonesville” is obviously a town in the boondocks.
The word boondocks comes from the Tagalog word bundok, meaning “mountain”. It was coined by U.S. Marines fighting against Filipino guerrillas after the Spanish-American War (1899–1902), for the rough hill country there. Later, American troops in the Philippines during World War II shortened it, and after the war it began to be used more widely.
Although we can’t be certain what time it is when Rory goes to the bus terminal with Jess, the express bus she took in the morning takes two and a half hours to get to New York, so to arrive in Hartford by 5.30 pm in order to be at the graduation ceremony by 6 pm, she cannot plan to leave any later than 3 pm.
Assuming Rory met Jess in Washington Square Park some time after midday, they have had time to eat lunch and catch the subway to a record store before coming to the bus terminal (which should have only taken 15 minutes to Times Square on the subway). They could have easily spent two, or two and a half hours together in New York.
Rory probably thinks she has timed everything perfectly – oh, how wrong she is!
Crank is a term to refer to someone with an unshakeable belief in something that most of their contemporaries believe to be false. The term was popularised in 1872, being applied to Horace Greeley in his campaign for the US presidency. He believed in the settlement of the Old West and a magnanimous Reconstruction of the American South, and was a proponent of socialism, vegetarianism, agrarianism, feminism, and temperance. Cranks today can take comfort in the fact that all Greeley’s cranky ideas were proven very sensible, and are mainstream today.
In North American, a crank can also be slang for a bad-tempered person. I’m not sure which one Luke was applying to Cy, the “crank in a hat”, but Cy seems to believe it’s the second one, because he makes a spirited defence by saying that Luke is the crank – he’s well known around town for being grumpy.
RORY: That is the closest to a farm that I ever wanna get. LORELAI: Amen, sister friend.
As far as I’m aware, “Amen, sister friend” is 1990s American slang to give encouragement or validation to a female friend, with “sister friend” implying a bond as close as sisters. Please correct me if I’m wrong!
LORELAI: [The Volvo’s] also excellent for cranking Metallica.
RICHARD: Cranking Metallica? … If that’s some sort of drug reference, it isn’t funny.
Lorelai says that Christopher’s Volvo is excellent for “cranking” Metallica, meaning “listening to Metallica loudly on the stereo”. The car really does have a great stereo system, but Lorelai is teasing Christopher, because Metallica is her favourite band, not Christopher’s.
RICHARD: Uh, you wanna narrow that [drink order] down for me? LORELAI: Hooch is hooch, Dad.
Hooch is old-fashioned American slang for hard liquor, which became common during the 1920s and the Prohibition era. It originated in the 19th century, and comes from the Hoochino Indians of Alaska. One small tribe, who called themselves the Hutsnuwu, had a reputation of brewing their own illicit alcohol which was extremely potent (presumably the information on making spirits was taught to them by Europeans, but nobody knows for sure).
EMILY: [sees Lorelai taking a pill] What are you taking? LORELAI: Roofies.
“Roofies” is slang for Rohypnol, a drug used to treat severe insomnia and assist with anaesthesia. It is widely known for its use as a date rape drug. It is an illegal drug in the US, banned from medical use and not allowed for import.