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.

Michael Douglas

LORELAI: Okay, so now the fact that I suggested painting Luke’s diner also means that I wanted to get him in bed. All of a sudden I’m trying to get any poor, unsuspecting person in bed with me. I’m like – I’m Michael Douglas!

Michael Douglas (born 1944) is a multi award-winning American actor and producer, with a long career in theatre, film, and television. He is married to Catherine Zeta-Jones, earlier discussed as one of the “pretty women” that Lorelai wonders if Luke’s ex-girlfriend Rachel resembles.

In 1993 it was widely reported that Michael Douglas was a sex addict and had entered rehab to be treated for his addiction (leading to much mockery). He refuted these claims, saying that he had gone into rehab to be treated for alcohol addiction, but the rumours persist – they were even published again in his 2012 biography by Marc Eliot, Michael Douglas: A Biography.

Diagnosed with cancer in 2010, Douglas told the public he had throat cancer caused by giving cunnilingus to many women, which did nothing to calm down the sex addiction rumours. In 2013 Douglas revealed he had actually had tongue cancer, and denied that there was any link with performing oral sex.

In January 2018, journalist Susan Braudy went public with claims that she had been sexually harassed by Michael Douglas in 1989 while working for him, including that he used inappropriate sexual language, and masturbated to orgasm in front of her. Douglas denies the allegations, although Braudy has shared corroborating evidence with the press. This has reignited the “sex addiction” rumours all over again.

Lorelai seems to have the common belief that people with “sex addiction” must be constantly trying to get random people to have intercourse with them, although such behaviour is probably rarer in real life than people think.

(Note: “Sex addiction” has not been accepted as a diagnosis by any mainstream psychological or psychiatric body, but there are support groups and treatment programs for it).

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.

Nancy Kerrigan and Tonya Harding

As they prepare for their ice skating date, Rory identifies herself as Nancy Kerrigan [pictured on the right], while Lorelai says she is Tonya Harding [left].

Nancy Kerrigan (born 1969) is a former figure skater, who became the US Champion in 1993. In 1994 she was clubbed in the knee by an assailant hired by the ex-husband of her rival Tonya Harding (born 1970), in an attempt to break her leg so that she would be unable to compete at the Winter Olympics.

The attack took place at the US Figure Skating Championships, ruling her out of the competition, which was won by Harding. Kerrigan made a good recovery from her injury (her knee was only bruised, not broken), and won silver at the 1994 Winter Olympics, held seven weeks later.

In March 1994, Harding pleaded guilty to conspiring to hinder prosecution of the attackers. She was fined and sentenced to community service, and was also forced to withdraw from the 1994 World Figure Skating Championships and to resign from the US Figure Skating Association. She was later stripped of her 1994 US Championships title and banned for life from participating in professional ice skating events in any capacity.

The fevered publicity generated by the scandal created a boom in professional ice skating, and may have even contributed to Rory’s interest in the skating film Ice Castles; like Lexie in the film, both Kerrigan and Harding came from modest backgrounds.

It is entirely within character that Rory identifies with the pageant-pretty “ice princess” Kerrigan who learned to fit in with the social conventions of the skating world, while Lorelai identifies with Harding – generally seen as an overly-dramatic emotional mess from the wrong side of the tracks. Harding also had issues with her mother, just as Lorelai does with Emily.

Errol Flynn

RICHARD (to Emily): You also knew that you wanted to marry Errol Flynn.
RORY: Really? Grandma had a thing for the pirate guy?

Errol Flynn (1909-1959) was an Australian-born American actor. First appearing in the 1933 Australian film In The Wake of the Bounty as mutineer Fletcher Christian, he got his first leading role in Hollywood in the 1935 film Captain Blood, where he played the rebellious buccaneer Peter Blood. After this he tended to be cast in romantic swashbucklers, often opposite Olivia de Havilland.

Flynn had a reputation as a womaniser and a voyeur, and in 1942 he was accused of statutory rape. Even though he was acquitted, his reputation was damaged. (Flynn actually picked up a teenage girl at the trial, and ended by marrying her; later he had a serious relationship with a 15 year old girl, adding some weight to the statutory rape accusations).

Emily’s attraction to a star seen as a hell-raiser and a rogue, dangerous for girls to be around, hints at a rather steamy side to her own sexual nature.

Iran-Contra

LORELAI: I kept information from you … Information that would have come out eventually. Like the Iran-Contra scandal.
RORY: So you’re Oliver North.
LORELAI: No, I’m Fawn Hall.
RORY: Mom.
LORELAI: Well, she was much prettier.

The Iran-Contra affair was a political scandal in the United States which took place during the second term of the Reagan Administration. Senior administration officials secretly facilitated the sale of arms to Iran, which was the subject of an arms embargo. They planned to fund the Contras in Nicaragua  through the arms sale, while at the same time negotiating the release of several US hostages held in Lebanon.

Lieutenant Colonel Oliver North [pictured] devised the scheme to fund the Contras, and was convicted in the Iran-Contra scandal in the late 1980s; however all charges against him were dismissed in 1991. Fawn Hall was North’s secretary who testified against him in court and was given immunity from prosecution in exchange for her testimony.