There’s something leonine about Colin Cowie, party planner to the stars. He’s cool and calm, his vibrato grabs the attention of everyone within earshot, and when the sun sets, he roars. Zambia-born and South Africa-raised, he hit it big when Oprah anointed him her event planner of choice in the early 2000s. Now, Cowie counts Qatari princes, Nicole Kidman, and Ryan Seacrest as clients.
That was all before Covid-19 put an 18-month halt on large-scale events. Flash forward to today, and we’re in a destination-wedding frenzy so unparalleled, there are big-budget celebrations seven days a week. According to Wedding Report, an industry group whose survey predicts 2.5 million nuptials in 2022, this will be the busiest year for event planners since 1984. And 45 of these ceremonies will be designed by Colin Cowie Lifestyle, up 50% from his pre-pandemic norm.
Cowie relies on a coterie of talented freelance producers and designers—and hard work. According to a CareerCast study, party planners have the fifth-most stressful careers, after military members and firefighters.
I learned that myself when I signed on to work a week for Cowie to see how it all goes down (the aisle) from the inside. In just seven days, I followed him on a tour of several cities, starting with a five-hour tasting in Manhattan and ending with a multimillion-dollar wedding weekend in Mexico. Along the way, I smuggled Fritos across borders and helped apprehend thieving rabbis. Here’s everything I learned about what really happens behind the scenes of a seven-figure party.
1. How to Spend $25 Million in One Weekend
The Colin Cowie Lifestyle brand is divided into two tiers: For a project of $250,000 or more, you can get one of his minions for the junior stylist equivalent. But Cowie himself “won’t touch a wedding if it’s under $1 million,” his planners say. The most expensive in recent memory was a party at a Mexican resort that cost $191,000 per attendee, more than $25 million in total. (Sadly, that wasn’t my assignment.)
Ideally, Cowie wants nine months to execute a wedding, though he did once turn around a party in six days for a couple who came to him in hysterics after firing their previous producer. Cowie and his team have their hands in every aspect of the planning process: They’ll hook up brides with gown and invitation designers, secure Broadway-caliber lighting and Michelin-quality food, and arrange for special fire code permits and garbage removal at private properties. The job even includes setting out gift baskets for neighbors to make nice before a weekend of raucous partying.
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So how do you drop $25 million between Friday night and Sunday brunch? When Cowie’s team takes over a hotel, it cranks up the food and service so high that it would be unsustainable otherwise. World-famous chefs and maitre d’s are flown in; added staff promise ultra-attentive service. The dishware is replaced; at one Middle Eastern affair, 40 VIP guests dined on settings that cost $12,000 each. Elaborate structures can be custom-designed for one-time use, such as a wooden deck sprawling over the edge of the ocean and a tented pavilion dripping with chandeliers, both built for the celebration I worked in Mexico.
Take the $11 million wedding that Erin Halley Reddy, one of Cowie’s executive producers, recently helmed: Almost $3 million went toward florals and $1 million more on the tent. The cocktail-hour sushi bar was about $30,000, as were the paper invitations. The average wedding in the U.S. runs $29,000 in its entirety, but in Cowie’s world, that won’t even cover the “concept presentations,” where mood boards are brought to life with food tastings, florals, and fully realized options for place settings.
2. Planners Secretly Love It When Things Go Wrong
The mark of a good planner is having a bulletproof Plan B for everything—and we mean everything. Rain on your wedding day? Sorry, Alanis, that’s not difficult to work around. Cowie usually has a second venue prepped and budgeted, just in case. Once, Reddy spent $500,000 of an eight-figure wedding budget on a backup ballroom space that luckily (phew?) went unused.
There are worse things than a black fly in your chardonnay, too. At one wedding, the father of the bride insisted on serving vintages from his private stash of rare wines, only to find at the last minute that every bottle had turned. “The sommelier got extremely sick,” recalls Robin Selden, a caterer who’s worked with Cowie. “Meanwhile, staffers were frantically running around town to buy crates of anything they could find.”
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Sometimes wedding disasters are so extreme, you wish they were ironic. Early in his career, Cowie constructed a large beachside tent lined with sumptuous Moroccan textiles—then the high tide wrecked it all 30 minutes before the celebration began. At a prominent Malibu wedding, the violinist ghosted, leaving Cowie to point a microphone at his car speakers while the bride walked down the aisle. (Cue the music of Kenny G, whose nuptials Cowie also arranged.)
Then there was the time almost all the guests were no-shows: The couple had insisted on using a rare gold-foil ink on the invitations, only to have it rub off in transit. “We basically mailed blank cards to 150 people,” Cowie says. Now he does a test mailing first.
3. Open Bars Are the Devil
“We once had a guest so drunk she fell over onto her wine glass and popped her silicone breast,” says Sophie Landry, one of Cowie’s designers, laughing. Cowie’s team always has an ambulance ready for worst-case scenarios, especially because curbing alcohol consumption at a private event is tricky. It proved difficult in Mexico, where the bridal party took nonstop tequila shots. Working that day as an assistant producer, I had the resort staff constantly circulating with extra glasses of ice water.
4. Smuggling And Cash “Gifts” Are Built Into The Contracts
It’s not an over-the-top destination wedding if there’s no private plane involved. Not for the guests: for Fritos and cake.
Cowie has shipped as many as 18 cargo containers and commercial planes (think 747s) full of furniture, decorations, and food items for single weddings in far-flung locales from the Middle East to the Midwest. Inside are briefcases full of steaks, crates of liquor—he famously taught Oprah how to shoot tequila (Don Julio 1942, natch)—thousands of AA batteries, and state-of-the-art lighting equipment. Once he brought an entire display of fireworks along on a chartered flight. “That time it felt like we were carrying a bomb through the sky,” he says with a chuckle.
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Cowie has legally cleared imports of 1 million (yes, million) plants from the Netherlands and Ecuador at a time. But delivering simple hangover remedies into hundreds of welcome bags always requires some smuggling—having one person carry thousands of Advil tablets makes them look like a drug mule. “The day before I leave for a destination wedding, I have my kids count out a ton of pills and divide them into little baggies,” Reddy says. Spread among a few dozen staffers, she explains, it’s easy to feign personal use.
Junk food and customized swag also get sneaked in: On our trip to Mexico, I was responsible for lugging two giant rolling duffels filled only with snack-size Fritos Honey BBQ Flavor Twists.
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And don’t forget money for unexpected “tips”! Cash running into five figures is spread across the team on every trip “to make problems go away,” as Cowie says. He’s used it to help 5,000 orchids miraculously rematerialize in Anguilla after they went missing upon landing. “The head of customs’ sister just happened to have 5,000 of the same flower at her ‘shop’ in town,” Cowie smirks.
Laine Sutten, one of Cowie’s longest-serving producers, “was essentially kidnapped” by her boat captain in the South Pacific when he jacked his fee to $20,000 for a ride back to her hotel from the deserted island where she was preparing a celebrity wedding. And it was all for naught: The event was eventually called off.
5. The Big Idea Comes First
“Our clients don’t come to us with the big requests—they come to Colin so he can give them the big suggestions,” says Alia Wilcox, Cowie’s lead designer. He’s synchronized a fleet of tall ships to shoot cannons for a rehearsal-dinner clambake in New England; he’s had Grace Jones “zoom in” on a zip line for a live performance (it was a stuntwoman, but it worked); he even coaxed the bride of a music executive to walk down the aisle in black lace Givenchy while Mary J. Blige belted When a Man Loves a Woman.
Selden once catered a Game of Thrones-themed wedding at a private estate where naked wenches covered in body paint served as human food trays by the pool. A body-painting station encouraged keen invitees to strip down, and everyone ended up in the home’s BDSM dungeon for the after-party.
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Bridal processionals rarely stray from the norm—but one of Cowie’s partners still talks about the bride who had six sheep accompany her down the aisle. “She was like a slutty Little Bo Peep,” he says. “She had the full bonnet, but her gown left nothing to the imagination.”
Elephants are more common than sheep. “There are three or four reputable vendors in the U.S. that specialize in elephant deliveries for Indian weddings,” says Hannah Cregg, an expert in securing permits to shut down streets for stampedes and setting up tricked-out trailers for the posh pachyderms. Such a production will set you back $10,000 to $15,000—pricier than riding on a Percheron horse but cheaper than arriving by helicopter.
6. The Villain Is Rarely the Bride
“The whole bridezilla thing just doesn’t exist at this level, where you’re getting everything you want,” Reddy says. One exception: “A bride once locked me in a closet and demanded, yelling, that I write her vows,” recalls Krista Cremidan, a Cowie executive producer. “I don’t think that marriage lasted very long.”
New-money moms are the worst, says Landry: “They can finally have the wedding they didn’t get when they were younger.” Adds Reddy: “Last year a bride’s mother made our videographer re-edit an entire wedding video because she wasn’t ‘starring’ in it enough.”
Fathers can be problematic, too. In Mexico the bride-to-be tipped me off with an email preapologizing for her dad’s inevitable bad behavior, and he sprung into action immediately on arrival, demanding we replace the rabbis who’d been flown in to bless the food with a new contingent of holy men from Miami. (One of these “good rabbis” shuttled in last-minute was caught stealing $5,000 worth of kosher steaks and six cases of wine.)
At a beach wedding, no one could find the father of the groom, who was in the ocean canoodling with his mistress. A staffer had to swim out to remind them not to miss the ceremony. The next task: finding him a dry tux, then plying his wife with Champagne.
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A-list entertainers often include a week’s worth of food in their riders, meant to provision their band and entourage. But some take it further: Several members of Cowie’s team watched, stunned, as Bruno Mars devoured 25 hamburgers in his greenroom all on his own. One pop diva left thickly applied spray tan all over a hotel’s walls and furniture, requiring eye-watering sums in reupholstery.
7. Prenups Can Pave the Way
On the odd occasion that a bride or groom gets cold feet, it’s usually because someone’s trying to stuff more cash into the prenup—using an embarrassing cancellation as a final negotiating chip.
Exhibit A: After an initial bout of prewedding jitters, one millionaire fiancé offered an extravagant ceremony as a mea culpa—“the cake was in the oven, the foie gras was on the private jet, and the groom had sent me to pick out a million-dollar necklace as a gift for his bride,” Cowie recalls. “Suddenly, I get a call: The fiancée wants a last-minute $10 million signing bonus for the prenup. I put the necklace back in its casing, and down came the tent!” Steven Mindel, the premier prenup lawyer of Los Angeles, whose client set overlaps with Cowie’s, says, “People think buying a house is the most expensive transaction of their life, but it’s actually their marriage partner.” He completes 40 to 60 such agreements a year.
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8. Wedding Desserts Are No Piece of Cake
It takes a year’s notice to hire Cowie’s preferred baker, New York-based Ron Ben-Israel, who makes 400 pieces of “cake couture” annually, costing from $4,000 to $100,000. (Peanuts when your menu costs $4 million.) For one pair of Middle Eastern royals, Cowie commissioned 2,500 hand-painted cakelets, each hermetically sealed to survive a transcontinental private jet trip. The total: $500,000, not including labor or transit.
Not all wealthy patrons can have elaborate 10-tier confections. “If the couple is short, I don’t do a high cake because they’ll look miniaturized next to it,” Ben-Israel explains. Animal motifs are also off-limits. “I find it repulsive to cut into a dog,” he says. Instead he’ll make furry critters from spun sugar as cake toppers.
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There are Great British Bake Off-style disasters, too—often related to melting buttercream and sagging layers in hot climes. For a wedding in Sri Lanka, baking the soft tiers amid crippling humidity and monsoon rains meant Ben-Israel had to “recruit 10 local children to continuously fan the cake and shoo away thousands of giant ants.” As for Ben-Israel’s signature topsy-turvy designs with tenuously balanced tiers on the diagonal? Those are intentional. They’re a “metaphor for marriage,” he says.
9. If You Don’t Have Millions?
The secret to good vibes, Cowie confesses, is simple: Set tables close together so the energy from one spills over to the next, “and put 10 people at a table that at other weddings have eight.”
Buffets are a no-no: They inspire the tacky behavior Cowie calls “vulture syndrome,” where guests pile plates high with incongruous items. Three courses presented in 90 minutes is ideal. “Four courses may sound chic, but it’s too much time sitting down.” In Mexico, I called out timing cues that corresponded with a 70-page event timeline; courses got turned over in exactly 13 minutes.
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Ceremonial essentials like the father-daughter dance should be no more than 45 seconds before onlookers can join in, and cake cutting occurs at the very end of the night—it’s bad manners to leave a wedding before it’s sliced.
A note on speeches: Limit them to two or three, and don’t let anyone exceed three minutes. “Make ’em laugh, make ’em cry, and you’re done,” Cowie says. My own tip? Don’t make the speech all about yourself, like the maid of honor in Mexico who shared tales of vomiting on herself, getting kicked off an airplane, and failing a college final.
Then again, the pros may just sidestep the hassle altogether. Says Landry, who’s in her early 30s and single: “When I get married, I swear, it’s gonna be a courthouse wedding.”
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