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.