As one of the most sought-after actors in Hollywood, Brad Pitt is no stranger to us. From The Curious Case of Benjamin Button to Fight Club, the charming American actor has proved why he held the title of People's Sexiest Man Alive twice. And, given such charisma Brad Pitt exudes, it comes as no surprise that he has been involved with a number of fellow A-listers throughout the years such as Jennifer Aniston and Angelina Jolie. Without further ado, let's take a look at the star's relationship history over the course of his career so far.

Born on March 21, 1963, Jill Schoelen rose to fame as a scream queen with notable roles in Chiller, Cutting Class, Popcorn, Rich Girl, and The Phantom of the Opera. Jill tied the knot with Anthony Marinelli in 1993 and split one year before their 10th wedding anniversary. At age 59, the American star has stepped back from acting and is leading a low-profile life.

Brad Pitt's first A-list romance was with Jill Schoelen after the two met on the film set of 1989's Cutting Class. Their relationship got so serious that she was even proposed to by Brad Pitt in 1989. Sadly, their romance ended just three months after the engagement.

Born on September 11, 1961, E.G Daily rose to fame as an actress and singer. Aside from many live-action movies such as Valley Girl, Dogfight, and The Rugrats Movie, the 61-year-old entertainer is also the owner of three popular albums including Wild Child, Tearing Down the Walls, and Lace Around the Wound.

Following Pitt's split from Schoelen in 1989, he went on to have a short-lived romance with E.G Daily. The couple was extremely private, however, and many sources claimed that Pitt was only looking for someone to console his wounded soul. Their love came to an end after a few months, but they have since remained good friends.

Born on October 19, 1963, Sinitta Malone did not only rise to stardom with unforgettable hits such as So Macho, Feels Like the First Time, etc but she also participated in several television shows including Loose Women, This Morning, and more. She got married to Andy Willner in 2002, sharing two children before divorcing in 2010.

One of her most well-known ex-boyfriends is Brad Pitt, who dated her on and off for two years between 1986 and 1988. The couple sadly broke up in 1988 due to a lack of affection as they were in long-distance love for too long. Not much is known about their romance as the Internet wasn't so popular at the time.

The ‘IT girl’ of Hollywood in the 90s, Juliette Lewis, was born on June 21, 1973. The Pasinetti Award winner appeared in several independent and arthouse movies such as Hysterical Blindness, Natural Born Killers, and Yellowjackets. She had 4 years of marriage with Steve Berra from 1999 to 2003.

Brad Pitt and Lewis, who is almost 10 years his junior, became one of the hottest young couples in Hollywood after they met while filming the television movie Too Young to Die? in 1989. The couple then shockingly broke up in 1993 after co-starring in Kalifornia without revealing any further reason.

The talented entertainer, Geena Davis, was born on January 21, 1956. She rose to fame as a soap opera actress and won an Academy Award and a Golden Globe Award in recognition of her roles in Beetlejuice and The Accidental Tourist. Other prominent films and TV shows with Davis' appearance include Exorcist, Grey's Anatomy, and Command in Chief.

After co-starring in 1991's crime and comedy-drama Thelma & Louise (which includes many hot scenes between them), Geena Davis and Brad Pitt were rumored to turn their on-screen chemistry into a real-life off-screen romance in 1992. However, the couple only stayed together for 1 year and ended their relationship in private.

American actress and businesswoman, Gwyneth Paltrow, was born on September 27, 1972. Many of her best films are Emma, Seven, and Proof, which brought her a Golden Globe nomination for Best Actress in a Motion Picture-Drama. She has been married to Brad Falchuk since 2018.

After meeting on the film set of Se7en, Brad Pitt and Gwyneth, who is 9 years his junior, fell in love and quickly became an iconic power couple of the 90s. While the Iron Man star almost tied the knot with Brad Pitt in 1997, the couple called it quits as Gwyneth admitted that she was not ready to marry at such a young age.

Born on February 11, 1969, Jennifer Aniston is one of the highest-paid and most sough-after actors in Hollywood. Apart from Leprechaun, The Good Girl, etc, she has become a household name with the hit sitcom FRIENDS, which brought her a Primetime Emmy, Golden Globe, and more. After two marriages, Jennifer is enjoying her single life at the moment.

One year after his failed marriage to Gwyneth Paltrow, Brad Pitt went on to date another fellow A-lister - Jennifer Aniston. The couple first met each other after being set up on a blind date by their agents in 1998 and quickly became a high-profile couple in Hollywood. In July 2000, the two tied the knot in Malibu, California. However, the couple announced their split in early 2005 after rumors about Brad Pitt's infidelity surfaced.

The highest-paid Hollywood actress, Angelina Jolie, was born on June 4, 1975. She has left her marks in acting, filmmaking, and fighting for human rights. Throughout the years, the audience has grown so familiar with Jolie through Maleficient, Wanted, Mr. and Mrs. Smith, and Eternals. Thanks to her immense service to the entertainment industry, she has received several awards, including an Academy Award and three Golden Globe Awards.

Jolie's high profile with Brad Pitt needs no introduction as it is considered one of the most admirable, but also controversial Hollywood marriages of all time. They started dating in 2004 after working in Mr. and Mrs. Smith (which gave Pitt his cheating allegations) and got married 10 years later, sharing six children. Unfortunately, the lovebirds separated in 2016 with Angelina accusing Pitt of being abusive and violent.

Born on November 6, 1972, Thandie Newton is one of the most sought-after actresses in Hollywood. She has gained popularity after starring in Mission: Impossible 2, Crash, Norbit, All the Old Knives, The Pursuit of Happyness, etc. In recognition of her service to the film industry, Newton has won several awards, including a Primetime Emmy Award and a British Academy Film Award, in addition to nominations for two Golden Globe Awards.

Their paths were connected when the duo got cast in the American gothic horror film Interview with the Vampire in 1994. Not much is known about this low-key romance, but they were rumored to have dated for roughly a year before parting ways in 1995.

Another Hollywood ex-girlfriend of Brad Pitt is Robin Givens, who was born on November 27, 1964. She was a famous actress, model, and director in the late 1980s with critically acclaimed roles in Boomerang, Head of the Class, Tyson, etc. Robin went through 2 marriages, and both of them lasted only 1 year.

The Sparks star was seen dating Pitt in 1986, at the same time that the actor was struggling with Sinitta. Loving a married woman, Brad Pitt could not maintain their relationship for more than a year as Mike Tyson - Davis' then-husband found out about this.