Cindy Crawford’s 30-Year Family Bond with George and Amal Clooney

George Clooney’s entourage is nothing short of iconic, featuring heavy hitters like Brad Pitt, Matt Damon, and Julia Roberts, along with close friends Rande Gerber and Cindy Crawford.

Cindy and Rande’s bond with George and his wife Amal Clooney extends beyond mere friendship, developing over four decades and encompassing business ventures, weddings, and children.

Cindy, a legendary supermodel, married Rande in 1998, but Rande’s connection with George dates further back to the mid-1990s. They first crossed paths at a bar within New York’s Paramount Hotel.

“George was filming a movie and stopped by one of my places. We had some tequila at the bar, and instantly hit it off. Many great stories start over tequila, and ours did too,” Rande reminisced in a 2016 interview.

Throughout their friendship, the group frequently vacationed together. During an Italy trip in 2002, George fell in love with Lake Como and ended up purchasing a $100 million lakeside villa.

In 2009, George, Rande, and Cindy jointly invested in a Mexican compound with two houses, designed by renowned architect Ricardo Legorreta.

Although initially planning to share one house, Cindy thought two houses would be more practical. “We have breakfast at my house, lunch at his, and dinner at ours,” Rande humorously described their arrangement.

Their “family” expanded in 2013 when George not only co-founded Casamigos Tequila with Rande, but also began dating Amal, a renowned human rights lawyer.

Rande praised Amal as an “amazing addition to the family,” humorously noting that George’s bachelor days ended not due to timing but because he found the right person.

As George and Amal’s relationship blossomed, George and Rande’s tequila venture also took off, originally intended solely for friends at private gatherings.

“It began as a private thing,” Rande told CNBC in 2017. “We didn’t aim to turn it into a business. George was focused on acting and directing, and I was content running bars and restaurants.”

With their friend Michael Meldman, they collaborated with a distiller in Jalisco, Mexico. “We wanted it to taste great and go down smoothly. It had to be a drink we could enjoy all day without getting hung over,” Rande explained.

The tequila remained private until their distiller notified them about unlicensed “samples” they were consuming excessively.

“The distiller called and said we had sent you roughly a thousand bottles each year—either you’re selling it or drinking way too much. This pushed us to go public, making it a bestselling brand today,” Rande shared.

Their tequila venture also strengthened the bond between Cindy and Amal. The two women became close friends, often spotted at events without their significant others.

“What I adore about Amal is she’s not just interesting but also interested in what you have to say,” Cindy once explained to People magazine. Cindy’s teenage children, Presley and Kaia, found it easy to discuss life and its challenges with Amal.

Rather than offering fashion advice to each other, Cindy and Amal prefer discussing intimate personal details, with Rande calling their friendship “perfect: both strong, intelligent, committed women.”

Casamigos played a role at George’s lavish three-day wedding to Amal in Venice in September 2014, for which Rande served as the best man. They flew in 100 cases of Casamigos for the celebration, covered exclusively by HELLO!

“We met in Italy, and we have a home there. We always knew it was where we wanted to get married,” George told HELLO!, adding, “Being Mr. and Mrs. Clooney feels pretty darn great.”

Tequila led to some funny moments too, like the time Cindy accidentally got into bed with George after a night of drinking. She mistook him for Rande in the dark, leading to shouts and laughter once they realized the mix-up. They even made commercials about it in 2013, showing them hilariously caught in bed together.

Casamigos was sold to Diageo in 2017 for $1 billion, but George and Rande remain actively involved. In early 2024, Cindy released Casamigos Jalapeno, a spicy variant on the classic tequila.

Casamigos also celebrated the birth of George and Amal’s twins, Ella and Alexander, with a funny Instagram video showing Rande delivering diapers alongside tequila cases.

“Special delivery,” the caption read. Rande and Cindy visited the twins in London soon after, calling them the “perfect blend of George and Amal.”

With Cindy’s children now adults, their bond with George and Amal has deepened. Kaia and her boyfriend Austin Butler were seen with the Clooneys in December 2023 at a New York event for George’s film, The Boys in the Boat.

Rande and George’s friendship remains solid. In 2013, George gifted $1 million to 14 friends, including Rande, to thank them for their support. In 2023, Rande revealed George also paid their taxes that year.

“It was an incredibly thoughtful gift,” Rande said. “But that’s just the kind of friend George is.”