Jennifer Aniston and Brad Pitt At A Sting Concert, 1999
Brad Pitt and Jennifer Aniston at a Sting concert in New York City? There’s nothing that can get more 90’s than that. The two even got up on stage with Gordon Matthew Thomas Sumner CBE during that live performance. Bran-Gelina got married in 2000, which was considered a success for a Hollywood couple. However, their marriage ended in 2005 when they filed for a divorce.
Eminem Kissing A Fan, 1999
Marshall Mathers, also known as Eminem, took the music world by storm in the late 90s. The Detroit native rapper became a success after releasing his hit song “My Name Is,” which premiered on Total Request Live. Eminem then became one of the most iconic rappers of all time.