Meeting for the first time in 1994 as their managers were friends, Jennifer Aniston and Brad Pitt went on their first date in 1998. One year later, they officially appeared as a couple at the Emmy Awards in 1999.
Jennifer Aniston and her boyfriend Brad Pitt attend the “Erin Brockovich” premiere at Mann Village Theatre in Westwood, California, on March 14, 2000 (Credit: Apega / WENN / Brian To / FayesVision / Vince Maher / Nikki Nelson)
A Wedding to Remember: Malibu Glamour at Its Peak
After two years of dating, they tied the knot in a lavish Malibu wedding on July 29, 2000. The star-studded ceremony featured around 200 guests, an astonishing 50,000 flowers, four live bands, a gospel choir, and a dazzling fireworks display.
Aniston told Rolling Stone in September 2001, “I had those typical jitters the day before my wedding, but the day of, I was just excited in a good way.”
Almost five years later, on January 7, 2005, they announced their separation and finalized their divorce on October 2. One year before their divorce, Brad Pitt fell in love with Angelina Jolie on the set of Mr. and Mrs. Smith.
A Painful Introduction: Jennifer Meets Angelina
Jennifer Aniston and Angelina Jolie met on the Friends set while Aniston was still married to Pitt. In an interview with Vanity Fair in 2006, she had only positive things to say about her husband’s future wife.
“It was on the lot of Friends—I pulled over and introduced myself,” Aniston recalled about her only meeting with Angelina Jolie.
“I said, ‘Brad is so excited about working with you. I hope you guys have a really good time.’”
Popular tourist attraction Madame Tussauds unveils its seasonal waxwork scene, featuring models of (L-R) Angelina Jolie as the Wicked Stepmother, Brad Pit as Prince Charming from Snow White, and Jennifer Aniston as Snow White at the Marylebone Road tourist attraction on December 15, 2005, in London, England
“That was really painful. It was a family, and I don’t do great with families splitting up,” Aniston added about Pitt’s withdrawal from their relationship. Jennifer’s own parents, Greek-born actor John Aniston and actress Nancy Dow, divorced when she was 9.
“It was hard to have such a wonderful constant in your life, a place to go every day, and then all of a sudden it’s not there.”
Just days after Jennifer Aniston appeared on the cover of Elle magazine wearing a slinky black leather dress, Angelina dons a near-identical frock to accompany Brad to a premiere in Los Angeles
“Because of the film, we ended up being brought together to do all these crazy things, and I think we found this strange friendship and partnership that kind of just suddenly happened. I think a few months in I realized, ‘God, I can’t wait to get to work.’ … Anything we had to do with each other, we just found a lot of joy in it together and a lot of real teamwork. We just became kind of a pair,” Jolie said about meeting Pitt on the set of Mr. and Mrs. Smith in the January 2017 issue of Vogue.
Promoting their new film “Mr. and Mrs. Smith” at ShoWest in Las Vegas in March 2005, Jolie and Pitt refused to get close to each other for photos outside the 20th Century Fox theatre.
The couple, who play married assassins in the new film, looked very uncomfortable. One ShoWest guest commented, “They looked like they really didn’t want to be there – and definitely not together.”
Pictured during ShoWest 2005, Jolie was named as the reason for Pitt’s split from his wife, Jennifer Aniston
Reacting to Aniston’s interview, Aniston admitted that she did not like how Angelina “homewrecker” Jolie stole her husband.
“There was stuff printed there that was definitely from a time when I was unaware that it was happening. I felt those details were a little inappropriate to discuss.” Aniston confessed to Vogue in a December 2008 interview.
“That stuff about how she couldn’t wait to get to work every day? That was really uncool,” she added.
Jennifer Aniston and Angelina Jolie rarely step on the same red carpet, but both attended the 2015 Critics’ Choice Awards, so we couldn’t help but do a fashion face-off! Who do you think looked best?
Jennifer’s Signature Style: Gucci Glam and Christian Louboutins
Opting for a sleek and sexy pantsuit, Best Actress nominee Jennifer Aniston showed off some cleavage in a burnt sienna Gucci Spring 2015 tuxedo, which she wore without any inner top (hence, the cleavage display).
Jennifer Aniston made a bold statement in a burnt sienna Gucci pantsuit, paired with layered gold necklaces and a daring plunging neckline
The abortion supporter decorated the sizzling look with layers of thin gold necklaces, highlighting the plunging neckline.
Jennifer Aniston styled her signature blonde locks in soft, natural waves and complemented her look with a glowing, minimal makeup palette that highlighted her radiant complexion and subtly lined eyes
She finished the ensemble with Christian Louboutin’s “Iriza” satin pumps and her signature perfectly layered blond locks. Her best accessory for the night was her fiancé, Justin Theroux, who looked dapper in his black suit.
Jennifer Aniston and Justin Theroux exuded style and elegance at the 20th Annual Critics’ Choice Awards, held at the Hollywood Palladium in Los Angeles on January 15, 2015
Angelina’s Versace Masterpiece: A Risk That Paid Off
While Jennifer was accompanied by her beau, Angelina went solo to the event.
Angelina Jolie complemented her radiant metallic silk Versace gown with soft, voluminous curls and subtle makeup, emphasizing her flawless complexion and signature smoky eyes at the 20th Annual Critics’ Choice Awards held at Hollywood Palladium in Los Angeles on January 15, 2015
The A-list actress, nominated as Best Director for her work in Unbroken, went for high glamour in a floor-length Atelier Versace gown that draped perfectly on her lean figure.
Angelina Jolie stunned in a flowing metallic silk Versace gown featuring elegant draping and a cape-like silhouette
She veered off from her typical black dresses, and we think the risk paid off as Angie looked magnificent in the metallic silk gown. Her makeup and hair were also flawless!
Angelina Jolie’s flawless makeup and soft, cascading waves perfectly complemented her shimmering silver gown, exuding old Hollywood glamour
Who do you think looked best? Angelina Jolie and Jennifer Aniston have both made unforgettable fashion statements over the years. Angelina’s timeless black gowns, such as the one she wore at the 2018 BAFTAs, have consistently exuded elegance and sophistication.
Meanwhile, Jennifer Aniston’s iconic looks, like her chic ensembles on Friends, have cemented her status as a style icon. For instance, she looked stunning at the 2024 Critics Choice Awards in a feather-accented, strapless Dolce & Gabbana jumpsuit. Their enduring influence continues to shape red-carpet fashion.