Inside Jennifer Aniston and Brad Pitt's $2.1 million fairytale wedding - Rokoto

Inside Jennifer Aniston and Brad Pitt’s $2.1 million fairytale wedding

This week marks 21 years since former Hollywood It couple Brad Pitt and Jennifer Aniston tied the knot. Though they didn’t have the happy ending the world hoped for, their short-lived relationship was so high-profile and enviable it remains tabloid fodder to this day.

The pair went on their first date in 1998 but kept their relationship quiet until making their red carpet debut at the Emmys in 1999, cementing themselves as Hollywood’s hottest couple. Then came the whirlwind engagement later that year.

They married on July 29, 2000, in a wedding that is reported to have cost US$1 million (approx. $2.1 million today), and which Jen would later call “fantastic” despite the absence of her estranged mother.

Brad Pitt and Jennifer Aniston cross paths on the SAG red carpet.
Brad Pitt and Jennifer Aniston, who remain friends despite their split, reunited on the red carpet in 2020 (Getty)

RELATED: Brad Pitt and Jennifer Aniston’s complete relationship timeline

The ring

Brad proposed to Jen with a US$500,000 (approx. $1 million today) diamond and platinum engagement ring by Italian jewellery designer Silvia Damiani, who Brad worked with for seven months.

The pair announced their engagement on stage at a Sting concert in November 1999.

Jennifer Aniston and Brad Pitt show off Jennifer's engagement ring onstage at the Beacon Theater during a Sting concert on November 21, 1999.
Jennifer Aniston and Brad Pitt show off Jennifer’s engagement ring onstage at the Beacon Theater during a Sting concert on November 21, 1999. (Getty)

The venue

Brad and Jen married on the top of a Malibu clifftop in California. The lavish ceremony took place on a five-acre property.

According to People, there were 50,000 flowers, four bands, a 40-member gospel choir and fireworks.

Tents were erected, lanterns were hung and the tables were adorned with roses, wisteria and tulips. The reception tent was illuminated by brown sugar candles imported from Thailand, as per Jen’s request. She apparently loves candles.

The bride and groom

Brad wore a four-button black tux designed Hedi Slimane while Jen was draped in a glass-beaded, silk and satin gown with a low back by designer Lawrence Steele.

She paired the dress with a pair of four-inch ivory suede Manolo Blahnik heels and a circular veil, which was draped from a pearl-and-Swarovski-crystal crown.

A source told People she wanted to look “sexy but pretty” and “to show off her toned arms.”

She carried a loose bouquet of Dutch Vendela roses and made her entrance after flower girls threw petals and blew bubblers.

Brad Pitt and Jennifer Aniston on their wedding day in 2000.
Brad Pitt and Jennifer Aniston on their wedding day in 2000. (People)

The bridal party

Jen had two bridesmaids. The first was Suddenly Susan actress Andréa Bendewald, who she has known since she 14. Jen would later serve as Andréa’s maid of honour at her 2001 wedding. Jen’s second bridesmaid was documentary filmmaker Kristin Hahn-Stringer, one of the first friends Jen made when she moved to LA and, later, her business partner.

The ladies wore pale green slip dresses while Jen’s flower girls wore cream silk frocks, also designed by Lawrence Steele.

Brad’s brother and best man Doug was dressed in a Prada suit. At one point he dropped the ring. Their dad Bill was the second groomsman, and their mother Jane and sister Julie watched from their seats.

Nancy, Jen’s estranged mother, did not attend the wedding. Jen and Nancy had a troubled relationship for years, but it was the publication of Nancy’s book From Mother and Daughter to Friends: A Memoir in 1999 that ended the relationship, hence Nancy’s absence from the wedding — Jen cut Nancy out of her life for 15 years and they reconciled just before Nancy’s death in 2016.

Meanwhile, Jen’s father, Days of Our Lives actor John Aniston, did attend. He had the special role of walking his daughter down the aisle.

“Jennifer looked beautiful,” John, who split from Nancy two decades earlier, told People at the time.

The vows

Brad and Jen wrote their own vows. Brad promised to “split the difference on the thermostat” while Aniston said she’d always make his “favourite banana milkshake.”

Later, they read more traditional vows in unison though Jen missed her cue.

“Oh, I’ve never done this before,” she joked. “With this ring, I thee wed, so that all the world may know my love for you,” Brad and Jen declared together.

The guest list

It was a star-studded event. Brad and Jen invited 200 guests including her Friends co-stars David Schwimmer, Lisa Kudrow, Matthew Perry, Matt Leblanc and Courtney Cox, the latter of whom arrived with her then-husband David Arquette.

Jen’s close friend Cameron Diaz was also in attendance, as was Brad’s Fight Club co-star Edward Norton and his date, actress Salma Hayek. David Spade, Jon Lovitz and Kathy Najimy also scored invites.

Brad Pitt and Jennifer Aniston at the 56th Annual Primetime Emmy Awards in 2004.
Brad Pitt and Jennifer Aniston, pictured here at the 56th Annual Primetime Emmy Awards in 2004, were together until January 2005 when they announced their intention to divorce. (Getty)

The reception

After the 15-minute ceremony, the newlyweds took their photos while guests ate shrimp, gourmet pizza and caviar, and drank Dom Pérignon champagne.

Dinner came at 8pm in the reception tent and guests dined on lobster, crab, peppercorn beef, risotto and pasta.

After the speeches, Brad and Jen hit the dance floor.

The cake

After the tossing of the bouquet and the garter throw, Brad and Jen cut their six-tier, white frosted wedding cake.

“They were looking into each other’s eyes when they fed it to each other,” singer Dakota Horvath, who performed at the wedding, told People. “And they were laughing with cake in their mouths.”

“It was a spectacular wedding,” said Jen’s father John.

Sadly, Jen and Brad split in January 2005. They issued a statement announcing the end of their marriage, and briefly touched on speculation about whether a third party, Brad’s Mr and Mrs Smith co-star Angelina Jolie, was involved. But that’s a whole other story.

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