George Clooney's squad is the stuff of legend – Brad Pitt, Matt Damon, Julia Roberts and of course, Rande Gerber and Cindy Crawford.
But Cindy and Rande's connection with George and wife Amal goes much deeper than just friendship, as their relationship has spanned four decades, a business deal, weddings and children.
Cindy, the OG supermodel, married Rande, 62, in 1998 but Rande's friendship goes back farther with George, with the pair meeting in the mid-1990s at Paramount Hotel hot spot, the Whiskey.
"George was shooting a movie there, and came into one of my places, and walked up to the bar. We both had a tequila together, and kind of became friends right there. Like many great stories, ours started over tequila! And the rest is history, as they say," Rande told Nobleman in 2016.
© Kevin MazurGeorge Clooney and Cindy Crawford shared a Mexican compound
Over their years of friendship they often vacationed together, with the group together in Italy in 2002 when George fell in love with Lake Como and decided to purchase his purchase his $100 million lakeside villa.
In 2009 George, 63, Rande and Cindy also purchased a compound in Mexico, which featured two houses – one for each family – and were designed by famed Mexican architect Ricardo Legorreta.
The original plan was for the group to share one home, but Cindy, 58, reportedly put her foot down, encouraging them to build on the same piece of land but smartly suggesting two homes may be better. "We have breakfast at my house, lunch at his, dinner at ours," Rande later joked, calling them "one big family".
© Kevin WinterGeorge falls in love
That family grew in 2013 when, as George and Rande began making plans to launch their tequila company Casamigos together, George was also falling in love with Amal Clooney, 46, a human rights lawyer whom he met at a dinner party.
Calling Amal a "great addition to the family," Rande once suggested that George's perpetual bachelorhood was never about timing but about waiting for the right person.
But as Amal and George grew closer, Rande and George began preparations to go into business together with Casamigos, a tequila brand which was originally a pet project for the pair and their friends, served exclusively at their parties.
© Denise TruscelloTequila business
"It was just for us," Rande told CNBC in 2017. "We didn’t really want to be in the business. We figured, George is an actor and a director. I own restaurants and bars and wasn’t looking to get into another business."
Together with their friend Michael Meldman, they worked with a distiller in Jalisco, Mexico, to find the perfect tequila: "It was important that it tasted great and didn’t burn going down. We wanted one that we could drink straight or on the rocks. One that we could drink all day and all night, and not be hungover in the morning."
They kept it private for two years until their distiller called them out on the number of unlicensed "samples" they were making.
"The distiller called and said, ‘Hey guys, we have a little problem: In the past two years, we’ve been sending you about a thousand bottles a year. Either you’re selling it or you’re drinking way too much — either way, we can’t keep calling it samples,'" Rande revealed, a conversation which saw the product go public and become one of the bestselling tequila products on the shelf today.
© David M. BenettTequila also helped the four bond, with Cindy and Amal becoming close friends over the years, often seen together at parties without their significant others.
Amal Clooney and Cindy Crawford = BFFs
“I think one of the things I love about Amal is that she’s not only interesting — she’s very interesting to talk to — but she’s also interested in your world as well,” Cindy once told People magazine, revealing that her then-teenage children, Presley and Kaia, also found it easy to talk to Amal about life and problems they may be facing.
With Cindy a supermodel and Amal a fashion icon, they don't offer each other advice, instead focusing on the intimate personal details of each other's mindset, with Rande praising their friendship, calling them "compatible: both strong, intelligent, committed women".
© Michael KovacGeorge and Amal's wild wedding
The alcohol was also, obviously, on hand for George's spectacular three-day wedding extravaganza to Amal in September 2014, which took place in Venice, Italy and for which Rande was George's best man. They flew out 100 cases of Casamigos into the city for the party, covered exclusively by HELLO!
"We met in Italy. We have a home there. We knew that was where we wanted to get married," George told HELLO!, adding: "My verdict on being Mr and Mrs Clooney? It feels pretty damn great."
Tequila has, however, also gotten the pair into trouble, with Cindy once accidentally crawling into bed with George when he crashed at their house after a night of drinking. Sharing the story in 2015, Rande revealed that Cindy once woke up at 3am to find her husband in a guest room, slipping into the bed and rubbing his back. Only it wasn't Rande but George, and the pair's shrieking left woke Rande, with the threesome ending up in the kitchen munching from the candy drawer and in hysterics.
They used the mishap for a series of commercials in 2013, which showed Rande discovering George and Cindy in bed together, and another where Cindy, and George's then-girlfriend Stacy Kiebler, discovered George and Rande in bed together.
Casamigos was sold to Diageo in 2017 for $1 billion but Rande and George still play an active role, and earlier in 2024 Cindy launched her own product, Casamigas Jalapeno, a spicy twist on the classic tequila.
The family grows
Casamigos also publicly congratulated George and Amal on the birth of their twins Ella and Alexander in 2017, with an Instagram video that showed Rande wheeling boxes of Pampers diapers next to cases of Casamigos.
"Special delivery," the caption quipped, while it was later revealed Cindy and Rande has visited the twins in London, with Rande calling them the "perfect mix of George and Amal".
© Steve.GranitzWith Cindy's children now grown, they have also solidified their bonds with George and Amal, with Kaia, and boyfriend Austin Butler, spotted with the pair in December 2023 at the Polo Bar in Midtown Manhattan for a post-screening party for George's directorial project The Boys in the Boat.
As for Rande and George's friendship, it continues to go from strength to strength; in 2013 Rande was one of 14 friends to whom George gifted $1 million as a token of appreciation for their support over the years, but in 2023 Rande revealed that George also paid all of their taxes for the year.
"It was an incredibly thoughtful gift," said Rande. "But that is truly the kind of friend George is."
