“Key his car”

LORELAI: I warned him. I warned him when I first met him, if he hurt her … Ah. Maybe I could key his car.
LUKE: Or better yet, you can key Taylor’s car, and tell him Dean did it.

To key a car means to use the sharp point of a key to scrap across someone’s car windshield or paintwork in order to damage it; often done out of spite as an act of petty vandalism.

Anna Nicole Smith and Mary Kay Letourneau

(Older man walks by.)
LORELAI: Pass.
RORY: Why?
LORELAI: Because I’m not Anna Nicole Smith. Next.
RORY: Two.
(Teenage boy on a skateboard goes by.)
LORELAI: Hmm, pass.
RORY: Why?
LORELAI: Because I’m not Mary Kay Letourneau.

Anna Nicole Smith, born Vickie Lynne Hogan (1967-2007) [pictured] was an American model and actress who first gained fame as a Playboy model, winning Playmate of the Year in 1992. She was perhaps best known for her 1994 marriage to J. Howard Marshall, an 89-year-old petroleum tycoon she had met while working at a strip club. It was speculated that she had married him for his money because of the age difference. Marshall died the following year, and there was a protracted legal case over his will; during it, Smith herself died, gaining no money from his estate.

Mary Kay Letourneau (born Mary Katherine Schmitz in 1962) is an American former schoolteacher who in 1997 pleaded guilty to raping a child, her twelve-year-old student Vili Fualaau, to whose baby she gave birth while awaiting sentencing. Due to a plea agreement, she was sentenced to three months in prison, and was not allowed contact with Fualaau for life. She broke the no-contact order soon after being released from prison, and was imprisoned again, this time for seven years, giving birth to another child in prison. After Letourneau was released in 2004, Vili Fualaau, now an adult, asked that the no-contact order be revoked, and they married in 2005. They legally separated in 2017, although they apparently still live together and are still in a relationship.

“Too cabin-in-the-woods?”

PARIS: Read my manifesto, I want your thoughts.
RORY: First thought – lose the word “manifesto”.
PARIS: Too cabin-in-the-woods?
RORY: Don’t open your mail.

A reference to domestic terrorist Theodore “Ted” Kaczynski (born 1942), also known as the Unabomber. In 1971 he moved to a remote cabin in the woods in Montana, where he lived as a recluse.

He first began his bombing campaign after witnessing the destruction of the wilderness around him, and between 1978 and 1995 mailed or hand-delivered a series of increasingly-sophisticated bombs that killed three people and injured twenty-three.

In 1995, Ted Kaczynski’s lengthy essay, Industrial Society and Its Future, (known to the police as the Unabomber Manifesto) was published in The New York Times and The Washington Post. He promised that if it was published he would desist from further terrorism, and police hoped that its publication would help lead to his identification.

That proved to be the case: Ted’s estranged brother, David Kaczynski, recognised his brother’s writing style from family records of letters that Ted had written to newspapers in the 1970s, and an earlier essay by Ted.

Ted Kaczynski was arrested in 1996; he pleaded guilty to all charges in 1998 and was sentenced to life imprisonment without parole. He is currently serving his sentence in a Supermax prison in Colorado.

Leopold and Loeb

EMILY: He [Chase] was just telling me that he actually grew up right around the corner from here.
CHASE: … Stone house on the corner.
LORELAI: Oh, the one with the Dobermans.
CHASE: That’s right. Leopold and Loeb.

This refers to Nathan Leopold Jr. (1904-1971) and Richard Loeb (1905-1936), collectively known as Leopold and Loeb. They were two wealthy students at the University of Chicago in 1924, when they kidnapped and murdered a 14-year-old boy named Robert “Bobby” Franks, who was a second-cousin of Loeb, and well-known to both the murderers.

Leopold and Loeb were of high intelligence, and committed the murder to demonstrate their intellectual superiority. They thought they would be able to commit the “perfect crime”, and that their intelligence meant that they could do as they like, even a thrill kill, and claim it as an experiment.

Arrested about a week later, they both confessed to the crime and were represented by the famous defence lawyer Clarence Darrow. The case became a media spectacle, and was billed as “the trial of the century”. Thanks to Darrow’s impassioned pleas, Leopold and Loeb escaped the death penalty and were given a sentence of life imprisonment instead.

Loeb was killed by a fellow prisoner in 1936, while Leopold became a model prisoner who made significant contributions to improving the conditions at Stateville Penitentiary in Illinois. He was released on parole in 1958, married, and moved to Puerto Rico, where he led a blameless life giving an enormous amount to the community in numerous ways – thus justifying Darrow’s defense that the death penalty would give them no chance to rehabilitate.

Chase’s parents obviously had a dark sense of humour when they named their pet Dobermans after two child killers.

Charlie Manson

CHRISTOPHER: I want to marry you …
LORELAI: You are out of your mind. You are completely insane. You have flipped your lid. Charlie Manson is freaked out by you right now!

Charles Manson (1934-2017) was an American criminal and cult leader, earlier alluded to as the head of the notorious Manson Family. His followers committed a series of murders in 1969 under his instructions.

Obsessed with The Beatles, Manson believed their song Helter Skelter was a warning of an apocalyptic war between whites and blacks, and that the Manson Family were being instructed to preserve the worthy from the impending disaster. By committing the murders, his followers would help precipitate the race war, and also control it, allowing them to escape from harm.

In 1971 he was convicted of murder and conspiracy to commit murder. Originally sentenced to death, his sentence was commuted to life imprisonment, which he served in California State Prison.

Lorelai believes Manson was mentally ill, and the prison system agreed. He was diagnosed with schizophrenia and paranoid delusions, had no remorse for any of his crimes, or apparent understanding of their magnitude, with highly controlling behaviour, and an exceptionally callous disregard for human suffering.

Claudine Longet

LORELAI: Who the hell is that anyways?
RORY: Claudine Longet.
LORELAI: The chick who shot the skier?
RORY: Uh, sure, why not.
LORELAI: Wow – Renaissance woman.

Claudine Longet (born 1942) is a French singer, dancer, and actress who was popular during the 1960s and ’70s. In 1976 she was arrested and charged with fatally shooting her boyfriend, the American Olympic skier Vladimir “Spider” Sabich in Aspen, Colorado. She claimed that the gun had discharged accidentally while Sabich was showing her how it worked.

Although the Aspen police gained evidence that Longet had cocaine in her system, and that her relationship with Sabich had become unhappy, they made procedural errors which meant that their evidence could not be used in court. Prosecutors noted that the autopsy report showed that Sabich had been bent over, facing away, and at least six feet (1.8 m) from Longet, which isn’t the usual position you take when showing someone how to handle a gun.

The jury convicted her of negligent homicide, and she was sentenced to pay a small fine and to spend thirty days in gaol in the manner of her own choosing. She chose to serve her sentence as weekend detention, and attracted public censure for going on holiday with her married defense attorney; they eventually married and still live in Aspen.

Longet was sued by the Sabich family, and the case was settled out of court. The conviction essentially ended Longet’s career, and she has lived out of the public eye ever since.

Rick James and Hugh Grant

RORY: Her [Paris’] dad’s like this big wig at a huge pharmaceutical company and they’re printing all the sordid details about it [his divorce] in the paper.
LORELAI: Ooh how sordid?
RORY: Well, it’s not the Rick James incident, but Hugh Grant should be feeling pretty good about himself.

American R&B singer Rick James (1948-2004) had several public scandals. In 1991, he and his wife were accused of holding a woman hostage for several days during a cocaine binge, tying her up, and forcing her to perform sexual acts. In 1993, while out on bail, he and his wife were accused of kidnapping and assaulting a female business associate for several hours. He was found guilty in both cases, sentenced to two years prison, and ordered to pay his second victim $2 million in damages in a civil suit. Released from prison in 1996, he was accused of sexually assaulting a woman in 1998, but charges were later dropped. It may be this final “incident” that Rory is alluding to.

British actor Hugh Grant (born 1960) [pictured] was arrested in Los Angeles in 1995 for receiving oral sex in a car from a Hollywood prostitute named Divine Brown. He was fined, placed on two years probation, and ordered to complete an AIDS education program. The incident occurred just before his film Nine Months was released, but he was able to gain public appreciation by speaking honestly about what he’d done and not making any excuses for his behaviour. As a result, no major damage was done to his career or reputation.

Mr. Geller’s scandalous exploits are apparently significantly worse than an encounter with a prostitute, but not as bad as the sexual assault allegations levelled at Rick James. We know that they must be sexual in nature, and of enough public interest to be reported in the newspaper. Other than that, they must be left to our imaginations.