The Saddest Moments in Angelina Jolie’s Life

Content warning: the following article mentions self-harm, suicidal ideation, addiction, and sexual assault.

Angelina Jolie has endless claims to fame. Throughout the years, she’s been known as an A-list actor, an international sex symbol, and an award-winning filmmaker. Jolie began her rise to fame in 1995 when she starred in “Hackers.” In 2000, the actor nabbed an Academy Award for her performance in “Girl, Interrupted.”

Jolie traveled to Cambodia in 2000 to film “Lara Croft: Tomb Raider.” After observing the country’s social and environmental issues, she took action by becoming a goodwill ambassador for the United Nations. The following year, she adopted her first child, Maddox Jolie-Pitt, from a Cambodian orphanage. Jolie’s family would eventually include six children. She has dedicated copious time and resources to philanthropy, founding several charitable organizations and tackling humanitarian issues such as public health, conservation, and education.

Aside from her acting career, Jolie has directed several films, including 2017’s award-winning “First They Killed My Father.” She claimed her place as a fashion maven in 2023 by opening her clothing store, Atelier Jolie, in New York City. Despite this illustrious resume, Jolie has endured significant heartbreak and trauma. From mental health struggles to a devastating loss, she has faced numerous challenges in her life.

Fans might know her as the star of blockbusters like “Changeling” and “Mr. and Mrs. Smith,” but Angelina Jolie was in the spotlight long before nabbing her first movie role. As the daughter of Oscar-winning actor Jon Voight, Jolie was born into Hollywood royalty. Throughout her childhood, she made several red carpet appearances alongside her dad. Jolie’s inaugural movie role came in 1982 when she made a cameo in Voight’s film, “Lookin’ To Get Out.”

Raised in Los Angeles, she attended acting school as a teen and seemed on track to become a young Hollywood success story. Despite her upbringing, she always felt like an outsider, even among her closest kin. As a child, Jolie struggled with depression and identity issues. “I didn’t know why I was so destructive and miserable,” she told Wall Street Journal Magazine in 2015. “I didn’t appreciate or understand my life.”

As she got older, Jolie felt increasingly empty and unfulfilled. “It took me a good while to feel I could be of use to anyone because I felt for a long time that I was a little crazy, that I was a little unhinged,” she told the Guardian in 2021. “If you would have asked me as a teenager if I could have been anybody’s mom, or of any use to the UN or write a book, I would have said absolutely not.”

During the late 90s, Jolie landed several movie roles that catapulted her into the big leagues. In 1997, she earned a Golden Globe for her role in “George Wallace.” Two years later, she delivered an Oscar-winning performance in “Girl, Interrupted.” Despite the fanfare, Jolie continued feeling depressed, lonely, and uninspired. At one point, she turned to self-harm. “It’s not a secret that I went through a self-destructive period, self-searching,” she told Parade in 2010. “I used to cut myself or jump out of airplanes, trying to find something new to push up against because sometimes everything else felt too easy.”

In 1996, Jolie married her first husband, actor Jonny Lee Miller. However, the romance did little to dull her pain. “I felt so off balance all the time,” she recalled in a 2003 episode of “20/20” (via ABC News). “I have everything that they say you should have to be happy and I’m not happy.” True fulfillment came in 2002 when she adopted her son Maddox Jolie-Pitt from Cambodia, feeling a deep sense of purpose.

Angelina Jolie was born in 1975 to actors Jon Voight and Marcheline Bertrand. When Jolie was about a year old, Voight had an extramarital affair and walked out on the family. Jolie had a strained relationship with her dad for the next few decades. Voight didn’t have much involvement in his children’s lives, and Bertrand struggled as the sole provider. “After her divorce, we had financial troubles,” Jolie revealed to Parade in 2010. “We never owned a home. We moved from small apartments to even smaller ones.”

In 2001, the father-daughter-duo briefly settled their differences when they appeared together in “Lara Croft: Tomb Raider.” However, Voight slammed Jolie in an interview, claiming she had “mental problems.” Jolie responded, “After all these years, I have determined that it is not healthy for me to be around my father, especially now that I am responsible for my own child” (via Entertainment Weekly).

In the following years, Jolie maintained a tumultuous relationship with her dad. Then, in 2017, they reunited once more. Speaking with the Hollywood Reporter, Jolie declared that this time their reconciliation was for good. “Jon and I have gotten to know each other — through grandchildren now — [and] we’re finding a new relationship,” she stated.

When Jolie burst onto the scene in the late 90s, fans were captivated by her beauty and smoldering stare. Despite being an It-girl, the actor had a tendency to flub her public image. During her early years, she gave several salacious interviews and was known for oversharing. Fans couldn’t stop gawking in 2000 when she shared an affectionate kiss with her brother, James Haven. Jolie’s antics garnered bad press, and she felt deeply hurt by some published stories about her. Looking back, she told Elle that she felt “misrepresented” by the media.

After Jolie adopted her son, Maddox, she was devastated when tabloids questioned her parenting skills. “People wonder aloud about whether I am an okay mother. That is obviously painful because it’s so important to me,” she told Cosmopolitan in 2003. “It’s hard to hear that people think I’m not a capable mother and a good person, that they just think I’m nuts.”

During her early career, Jolie also contended with rumors about her alleged substance misuse. In 2010, Life & Style (via Huffpost) published an interview with a man claiming to have sold drugs to Jolie in the 90s. He alleged that Jolie had been addicted to cocaine and heroin. For her part, Jolie chose not to comment publicly about the allegations but hinted at her past drug use in a 2015 interview with Vanity Fair, saying she was “fascinated” by heroin.

In 1998, Jolie starred in the biopic “Gia,” earning a Golden Globe Award. The role left her feeling depressed. Shortly after, she decided to end her life, hiring a hitman to kill her. Jolie felt that her family would have an easier time accepting her death if they believed it was caused by murder rather than suicide. However, the hitman convinced her not to go through with the plan. Jolie credits her children for giving her the strength to keep going. “Having children saved me — and taught me to be in this world differently,” she told Vogue.

Despite grappling with numerous tragedies, Jolie remains grateful for her life. Speaking with The Times in 2021, Jolie admitted she still struggles with mental health issues. “I’ve had a very blessed life but I’ve had my own challenges,” she confessed. Sadly, Jolie’s mental health took another hit after her separation from Brad Pitt. Amid the messy divorce proceedings, custody battles, and legal disputes over shared properties, life has been a roller coaster for the superstar. Speaking with Vogue in 2024, Jolie admitted she’d been pushed to her breaking point. “I feel a bit down these days,” she confessed.

In 2017, Jolie was stricken with Bell’s Palsy, a neurological condition causing temporary facial paralysis. Eventually, she made a full recovery but acknowledged that her condition was likely caused by the stress of rebuilding her life after the breakup. “Sometimes women in families put themselves last until it manifests itself in their own health,” she told Vanity Fair.

Following her breakup with Brad Pitt, Jolie put on a brave face for her kids. “I do not want my children to be worried about me,” she emphasized to Vanity Fair in 2017. “I think it’s very important to cry in the shower and not in front of them. They need to know that everything’s going to be all right even when you’re not sure it is.”

After their separation, Jolie and Pitt entered a bitter custody battle that lasted several years. In 2021, Pitt sued Jolie for selling her share of Château Miraval, a French vineyard that she had previously co-owned with him. Pitt claimed that Jolie violated a verbal agreement when she made the business deal. Jolie responded by filing a counter suit, claiming that Pitt refused to sell his share to her unless she agreed to sign an NDA.

In 2024, Jolie filed new court papers stating that Pitt’s legal actions were malicious. Her lawyers wrote, “It is extremely painful for Jolie to have to defend herself from Pitt’s lawsuit — itself another example of Pitt’s unrelenting efforts to control and financially drain her.”

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