Anvil

LORELAI: Hey, four menus, a coffee and an anvil please.
LUKE: What’s the anvil for?
LORELAI: For Rune.

Lorelai is referring to a common trope in cartoons where an anvil is dropped on a character’s head with hilarious results. It seems to have first been used in Disney animated films, and was perfected by Warner Bros. in their Looney Toons cartoons. (Possibly not a coincidence that Lorelai sees Rune off with a “Bye, Loon”.

The comedy anvil drop may have its origins in real life. A traditional celebration on the Fourth of July in America was launching an anvil into the air with gunpowder from atop another anvil, then watching it fall onto the other anvil with a thud. Presumably everyone stood well back during this exciting spectacle and hopefully nobody got an anvil on the head.

“Hey sailor”

SOOKIE: Not too much [make up].
LORELAI: No – just enough to say, “Hey sailor”.

A joke flirtatious catchphrase, supposedly from a prostitute or promiscuous woman (or man) to a male sailor, as if he is sexually frustrated after months at sea.

Lorelai is saying Sookie just needs enough make up to attract the attention of a desperate and not very fussy man. Not all that flattering, but Lorelai’s jokes rarely are.

Charo

LORELAI: Rory, there are only two things that I totally trust in this entire world. The fact that I will never be able to understand what Charo is saying no matter how long she lives in this country – and you.

Charo (born Maria Martinez Molina Baeza in perhaps 1941) is a Spanish-American actress, comedian, and flamenco guitarist. In the late 1960s and 1970s Charo frequently appeared on American television as a guest star, and she has had a successful musical career in Latin America for five decades.

Her stage persona has an exuberant manner, wears flamboyant costumes, speaks broken English with a heavy Spanish accent, and uses the meaningless catchphrase “cuchi-cuchi” a lot – hence Lorelai’s difficulty in understanding her.

Oscar Levant

Lorelai jokingly tells Emily that if Rory grows up bitter and filled with regrets, she could become a crazy Oscar Levant type of celebrity.

Oscar Levant (1906-1972) was an American pianist, composer and comedian. A serious composer who wrote numerous film scores for Hollywood and appeared in several films as a pianist, he was famous for his eccentricity and acid wit. He was a panellist on radio and TV for many years, and was open about his many neuroses.

Mister Kelly’s

BABETTE (to Dean): There used be a great club there called – what was it called baby?
MOREY: Uh … Mr. Kelly’s.
BABETTE: Oh, yeah – Mr. Kelly’s. You ever go there?

Mister Kelly’s was a nightclub in Chicago, which began in 1953. From 1956 onward it became a place where many entertainers, especially jazz singers and comedians, began their careers, including Barbra Streisand, Lenny Bruce, Eartha Kitt, and George Carlin. The nightclub closed in 1975, so it isn’t possible for Dean to have ever gone there.

Lorelai’s Joke

LORELAI: All right, everybody, I need your attention, your attention please. This is a very serious moment. Two priests, a rabbi and a duck —
RORY: Mom.
LORELAI: All right, I’m kidding.

The old joke Lorelai pretends to start telling goes: Two priests, a rabbi, and a duck walk into a bar. The bartender says, “What is this, a joke?”. The punchline is because priests, rabbis, and/or ducks in bars are a common feature in jokes.

Henny Youngman

EMILY: Everything’s a joke. Everyone’s a punch line … My daughter – Henny Youngman.

Henry “Henny” Youngman (1906-1998) was a British-born American comedian and violinist famous for his one-liners – his most well known being the classic, “Take my wife … please”. He was known as The King of the One Liners. His routine consisted of simple one-liner jokes, broken up with interludes of violin playing. The hyper-successful Youngman performed on stage until the end of his life, and made many appearances on television.