Ms. Jackson

This 2000 song by alternative hip-hop duo OutKast begins playing in the background when we first see Tristan and Summer arguing; Summer identifies it as a “good song” before starting to dance to it.

Ms Jackson is a single from OutKast’s album Stankonia, which went to #1 in the charts and on the hip-hop charts. It won a 2002 Grammy Award for Best Rap Performance by a Duo or Group, and is regarded as one of the best songs of the 2000s.

The song is about the difficulties of breakups, and the animosity that a woman’s mother often has for her daughter’s ex-boyfriend. It’s a hint of the anger that Lorelai feels toward Dean, although she hasn’t expressed it for fear of upsetting Rory.

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