Some five months after he got down on one knee, midway through a homemade pasta dinner—his Aunt Rosemary Clooney's track "Why Shouldn't I?" the signal it was time to pull out the 7-carat diamond he'd commissioned—the newly formed power couple rounded up 100 of their nearest and dearest for Venetian vows that would see them criss-crossing the city's famed maze of canals for four days.
"We didn't tell anybody else that we were going to do it," George later recalled to The Hollywood Reporter, "but eventually somebody figured it out."
And once people got wind of the plans, "it became an event," he continued. They bussed the four hours or so from his 18th century Lake Como villa to Venice "and once we got on the boat, there were so many paparazzi and so many people standing there waiting. We were sitting down in the boat, and I was like, 'You know what? Why are we hiding? Why are we ducking? We shouldn't be ashamed of this.' And we got up and waved."
Because their Sept. 27, 2014 traditional ceremony was every bit as spectacular as any red carpet event with everyone from Emily Blunt and John Krasinski to Matt Damon, Bono and Anna Wintour turning out to watch the long-professed bachelor, who'd insisted he'd sooner slip back into Batman's cowl than marry again, pledge forever to the woman he never saw coming. (Brad Pitt and then-wife Angelina Jolie were tied up with work commitments; Ben Affleck was attending the premiere of his film Gone Girl, joking to E! News, "You know, some of us have to work.")
"I dated a lot of really terrific women, but Amal showed up and suddenly it was like, 'Well, this is different on every level for me,'" the 62-year-old told The New York Times of the decorated Oxford grad, 45, who turned up to a dinner party at his Italian spread and reserved a spot in his heart.
Suddenly, spending his life with one person, the right person, was the most obvious choice. "There is no question that having Amal in my life changed everything for me. No question," he said. "It was the first time that everything that she did and everything about her was infinitely more important than anything about me."
So, no, their vows weren't going to be casual.
"George and I wanted a wedding that was romantic and elegant," Amal explained to Vogue that year. Which is why she found herself in designer Oscar de la Renta's New York City showroom some two months before the planned extravaganza.
She and the CFDA president had already "looked at a lot of evening dresses and wedding dresses together," de la Renta told the outlet, "and we discussed what she liked. That gave me the idea of what she wanted."
The end result was layers of ivory tulle appliquéd with fourteen yards of Chantilly lace, the bodice then hand embroidered with beading and crystals, and a coordinating cathedral-length veil, the perfect look for that long walk down the aisle in a place her future husband dubbed "the most romantic city in the world."
But first there was much celebrating to do in the coastal Italian city, starting with the couple's separate bachelor and bachelorette bashes on Friday, Sept. 26.
Hours after they made the trip east, Amal slipped into a cocktail dress by Sarah Burton for Alexander McQueen (as in the person tapped to create Kate Middleton's wedding gown) and joined designer sister Tala Alamuddin, editor mother Baria Alamuddin and a few friends at the Aman Canal Grande Venice where she and George would wed the following evening.
Her groom's party boat (containing his close pal and fellow Casamigos Tequila founder Rande Gerber), meanwhile, continued on to Tuscan spot Ristorante Da Ivo where George had phoned just moments earlier "and said, 'I want to come over,'" owner Giovanni Fracassi revealed to E! News. "It was a very intense night."
Leaping into action, Giovanni rearranged diners in the 37-seat canal-side venue and put screens over the window so George's group could enjoy their tortellini with black truffle and risotto with mushrooms (and the three bottles of Casamigos they toted along!) in peace.
"He clearly looked as if he had been celebrating all day but there was no sign of the usual madness associated with a bachelor party," a fellow diner shared with E! News at the time. "Just lots of happiness."
That, of course, remained the theme the following evening when everyone returned to the opulent Aman Venice for the main event.
The gilded halls of the seven-star resort, covered in white roses, hydrangeas and lilies, and a seemingly endless supply of candelabras, provided the backdrop for the 30-minute ceremony officiated by former Rome Mayor Walter Veltroni.
There was a rendition of Irving Berlin's "Always", the song George's parents danced to at their vows, and speeches from loved ones, including Baria, who gushed of her future son-in-law (in a Giorgio Armani tux), "'George, we love you truly, deeply and sincerely. We enjoy your charm, your wit, intelligent conversation and generosity. You are simply perfect.'" Finally, the pair sealed their forever with a lengthy kiss.
Then it was off to the five-course meal of polenta with wild mushrooms and lobster risotto, the cutting of a towering, four-tier art deco cake and a first dance that saw the couple sway to "Why Shouldn't I?", the song that started it all.
Some 250 bottles of champagne and a reported 100 cases of Casamigos kept the party going until 5 a.m., the bride having changed into her second Oscar de la Renta look of the night—a tiered, Gatsby-inspired beaded number made for partying.
"George and Amal radiated love all night," Baria told People. "The wedding was so unbelievably special, it was legendary."
And it kept going, the newlyweds toasting their friends and family once again on Sunday afternoon with a poolside bash at the Cipriani Hotel. When George and Amal (in a lace Giambattista Valli Couture frock with floral embellishment) arrived, a source told E! News at the time, "everyone cheered so loudly you could hear it down the canal."
A picnic-style buffet of what the source dubbed "hangover food" (think: bacon and egg club sandwiches, fries, burgers, cheesecake) was laid out to fuel another round of drinks and dancing. "The champagne corks started popping and they cranked the music up really loud," noted the source. "It was a variety of songs, but funk style mostly—things like James Brown and really cool fun party music. There was a DJ there playing and it was a lovely, sunny and warm afternoon. Some people were jumping in and out of the pool and swimming...it was a really fun afternoon."
Following a pause for wardrobe changes, guests reconvened in the luxury hotel's eatery for another out 'til dawn evening. "It was a party to end the weekend festivities before people fly home Monday," explained a source. "It was just such a cool and classy way to round off a really incredible weekend."
Of course, Mr. and Mrs. Clooney had one last detail to attend to, turning up at the municipal building the following afternoon (Amal chose a cream Stella McCartney suit for the event) to legally cement their marriage in a five-minute civil ceremony.
A nonstop weekend of celebrating and champagne toasts that absolutely lived up to the hype (estimated price tag: $4.6 million), "the friends, the families, the atmosphere, everything," said Baria, "will stay with me all the rest of my life."
And, yet, the best part, guest Bill Murray insisted to E! News at his St. Vincent premiere days later, was simply "those two people finding each other. It's just amazing that those two people—the way they are—found the other person. It's almost surreal. I am so happy for them!"
Almost as thrilled as the Clooneys were for themselves.
Because it was not long after their dream vows, that the newlyweds got around to the idea of potentially having children. "After the wedding, Amal and I were talking and we just felt like we'd gotten very lucky, both of us, and we should share whatever good luck we've got," George explained to The Hollywood Reporter. "It would seem self-centered to just have that belong to us."
Having seen George flip his stance on marriage, friends had expected babies might be next.
"It wasn't a question for many years—it was a total nonstarter," pal Matt Damon told E! News in 2017, while promoting his action film The Great Wall. "But once he met [Amal], everything changed." So when George confessed they'd be welcoming twins ahead of their third anniversary, "I wasn't surprised," said Matt. "I'm extremely happy for them but once he met her, I had a feeling that was in the cards."
It was a perception shared by much of his inner circle. Cindy Crawford, wed to George's Casamigos Tequila cofounder Rande, told E! News, "It really took Amal, I think. She's just so amazing and they're just so happy. It just seemed like a natural next step."
Years later they remain in lock-step, the pair spending the pandemic lockdown penning each other love notes.
"I'll write a letter and slip it on her desk, or she'll write a letter and leave it under the pillow," George told AARP The Magazine in 2021, "I'm a big believer in letters."
And simply embracing where his story might lead next, even if it's an ending he didn't anticipate. "There are some people, their goal was, 'I have to have children.' Mine wasn't. I wasn't looking at life, going, 'My life will be unfulfilled without children.' I felt like I had a pretty full life," the Tomorrowland star explained to Today host Hoda Kotb in March 2021. "Then I met Amal and realized that my life had been pretty empty. And then when you throw these two kids in there, then suddenly you realize how incredibly empty it was."
Welcoming now 6-year-old twins Alexander and Ella gave him, "a sense of belonging and a sense of home and unconditional love," he continued. "All the things that you were hoping you could get from a really good career and a dog. You realize that this is a lot more than that."
This story was originally published on Monday, Sept. 27, 2021 at 3 a.m. PT.