Brad Pitt’s Ex-Girlfriends (Celebrity Dating Timeline)

From the beginning of his career in Hollywood, Brad Pitt has been linked up in the news with some of the most talented, interesting, and beautiful women in the industry. Though his relationships haven't always lasted past the first high profile red carpet picture opportunity, they've stayed in the consciousness of his fan base and the media, who love to bring up his entire dating history every time he is seen with a new woman on his arm.

Brad Pitt & Sinitta Malone, 1984 – 1988

Sinitta Malone is a British singer who became famous in the mid'80s for her hit song "So Macho". She had a busy career during the decade, singing and dancing and touring with her mother.

Sinitta Malone

She also acted in movies like Shock Treatment and West End productions including Cats. She and Pitt had an on-again off-again relationship for several years.

Brad Pitt & Robin Givens, 1986 – 1987

Model and stage/television/film actress Robin Givens met Pitt on the set of her popular 80's series Head of the Class.

Robin Givens

Her relationship with him was much less tumultuous than that with her ex-husband Mike Tyson. During her divorce with Tyson she was labeled "The Most Hated Woman in America" at one point.

Brad Pitt & Christina Applegate, 1989

Pitt attended the 1989 MTV Video Music Awards with Married...With Children star Christina Applegate.

Christina Applegate

They didn't seem particularly serious about each other at the time, and both went on to date other people and have lucrative television and film careers.