Britney Spears

RORY (upon first seeing her new school uniform): I’m gonna be in a Britney Spears video?

Britney Spears (born 1981) is an American pop singer. Her debut album was … Baby One More Time, released in 1999. In the music video for the title track, Britney Spears is dressed as a Catholic schoolgirl in a uniform. The single … One More Time went to #1 worldwide.

Eminem

LANE: Rory, if my parents still get upset over the obscene portion size of American food, I seriously doubt I’m gonna make any inroads with Eminem.

Eminem (born Marshal Mathers III in 1972) is an American rapper who was the best-selling musical artist of the 2000s. His first album was released in 1996, and he gained mainstream success with The Slim Shady LP in May 2000.

Woodstock ’99

When Lane changes clothing on her way to school, she wears a tee shirt which reads WOODSTOCK ’99. In 1999 a large-scale musical festival was held in upstate New York to commemorate the thirtieth anniversary of the 1969 Woodstock Festival. Unlike the peaceful event of the 1960s, the 1990s festival was marred by incidents of  violence, fire, and rape. A CD was released in 1999, and a DVD in March 2000. It seems very unlikely that Lane attended the festival, but she may have got the tee-shirt included when buying either the CD or DVD.

Macy Gray

LORELAI: Wow, you’re crabby.
RORY: I’m sorry. I lost my Macy Gray CD and I need caffeine.

Macy Gray (born Natalie McIntyre in 1967) is an American R&B singer known for her distinctive raspy voice. The CD which Rory has lost is Gray’s debut album On How Life Is, released in 1999. Her best-selling album to date, it was widely praised by critics.

RuPaul

RORY (responding to Lorelai’s offer of cosmetics): God, RuPaul doesn’t need this much makeup.

RuPaul (born RuPaul Charles in 1960) is an American drag queen. In 1993 he found mainstream success with his dance album Supermodel of the World; several of its singles became hits, and two more albums followed in the 1990s. RuPaul was signed as a model with cosmetics company MAC, released his autobiography in 1995, and got his own talk show in 1996.

There She Goes

This song by English indie rock band The La’s is the first track to play during the pilot, and accompanies Lorelai on her walk through the town to the diner. First released in 1988, There She Goes initially failed to chart in the US, but after being remixed for their 1990 self-titled debut album went to #13 in the UK and #49 in the US.

Where You Lead

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The theme song for Gilmore Girls was originally written in 1970 by Carole King and Toni Stern, and released on King’s 1971 album Tapestry – one of the best selling albums of all time. Uncomfortable with the song’s theme of a woman happily and blindly following a man she loves, Carole King stopped performing it in concert.

When Amy Sherman-Palladino asked King’s permission to use the song for Gilmore Girls, Carole suggested she  re-record the song, changing the lyrics slightly to make it suitable for a mother-daughter relationship, and performing it as a duet with her own daughter, Louise Goffin. Since then, Carole King and Louise Goffin have performed the new version of the song in concert together.