Brad and jen

Jennifer Aniston and Brad Pitt

Brad Pitt and Angelina Jolie are engaged! Before he was one half of Hollywood's most glamorous power couple, Brad got his start acting more than 20 years ago.

Jen Brad

Jen Aniston&Brad Pitt.

15.8k Likes, 65 Comments - 𝕻𝖔𝖕 𝖈𝖚𝖑𝖙𝖚𝖗𝖊 (@90s.dios) on Instagram: “Jennifer Aniston & Brad Pitt in London, 1999. Who’s your favorite Hollywood couple?👇🏽”

The amicable exes were all smiles for the first image of the highly anticipated charity event. The 'Fast Times at Ridgemont High' virtual table read will tak...

Including some from before he made it big.

Browse The 54th Annual Primetime Emmy Awards - Backstage and Audience latest photos. View images and find out more about The 54th Annual Primetime Emmy Awards - Backstage and Audience at Getty Images.

2,075 Likes, 23 Comments - 💖Brad Pitt italian fanpage💖 (@bradpitt.italian.fanpage) on Instagram: “I really like and respect both Angelina and Jennifer, never on the Brennifer or Brangelina side…”

Fast-forward to a year later and baby rumors started to circulate. The couple was spotted enjoying some time together amidst their busy work schedules during Milan Men's Fashion Week on June 28, 2001. Around the same time, a German magazine garnered much attention after they claimed to have obtained a quote from Pitt saying that they were starting a family.