Context:

Reflecting on pop culture from 20 years ago, certain moments have not aged well, such as 'fat Monica' from Friends and Aaliyah's song written by R. Kelly. Diddy's controversial hosting of the MTV Video Music Awards, Tom Cruise's erratic behavior on Oprah's show, and the problematic 'Diversity Day' episode of The Office are highlighted as cringeworthy events. The portrayal of female characters, as seen in Jessica Alba's role in Fantastic Four and the Manic Pixie Dream Girl trope in Elizabethtown, demonstrates outdated gender norms. Additionally, the depiction of race in films like King Kong and Crash, as well as the inappropriate humor in Waiting..., reveal cultural insensitivities of the time.

Dive Deeper:

• Pop culture moments that haven't aged well include Friends' 'fat Monica' portrayal and Aaliyah's song produced by R. Kelly, which are now seen as insensitive and problematic.

• Diddy hosting the 2005 MTV Video Music Awards, with promotional jokes about his infamous parties, is now considered in poor taste due to recent allegations against him.

• Tom Cruise's chaotic appearance on Oprah, where his excessive display of affection for Katie Holmes became iconic for its awkwardness and remains cringeworthy today.

• The 'Diversity Day' episode of The Office is criticized for its racially insensitive portrayal of diversity training, highlighting issues with using slurs even in a comedic context.

• Jessica Alba's character in Fantastic Four was over-sexualized, using her superpower as an excuse for her to appear in underwear, reflecting outdated gender roles in superhero films.

• The depiction of race in Peter Jackson's King Kong, particularly the portrayal of Skull Island's native people, is criticized for perpetuating racial stereotypes in a horror context.

• The film Crash, awarded Best Picture over Brokeback Mountain, is now viewed as having a narrow and absurd perspective on race, contrasting with the latter's cultural significance.