Most Memorable Celebrity Weddings of All Time

After meeting on the set of her “Material Girl” music video, rising Queen of Pop Madonna and breakout big-screen bad boy Sean Penn began dating in 1985. Six months later, on Aug. 16 (Madonna’s 27^th birthday), the two wed in a lavish Malibu ceremony. Two hundred and twenty guests (including Rosanna Arquette, Christopher Walken, Carrie Fisher, Andy Warhol, Diane Keaton, and Tom Cruise) stood poolside at real-estate developer Dan Unger’s $6.5 million home to watch the two exchange vows above the Pacific Ocean. Escorted by her father, the bride wore a custom strapless gown created by her Madonna Live: The Virgin Tour designer Marlene Stewart, while the groom donned an off-the-rack Versace tux. After a brief ceremony, Penn lifted his new wife’s veil, and the couple shared a kiss as the theme from “Chariots of Fire” played. Later, there was sushi, there was Cristal, there was catering by Spago. In other words, it was the most 1980s wedding of the 1980s. It was also one of the first to be besieged by helicopters hovering not-so-high above the event, carrying tabloid photographers hoping to get their money shot. The cutthroat battle set a dangerous precedent for celebrity wedding coverage that has some couples so concerned about privacy they go to extreme lengths to protect it. Like renting out Madison Square Garden and/or staging a fake event. Maybe.

On Sept. 21, 1996, America’s chosen royals were married in a secret ceremony on Cumberland Island, Georgia. Kennedy had fallen in love with the tiny coastal town years prior to meeting his bride, but she, too, became enamored of the remote locale. Most of the island has been deemed a national park, so the couple held the reception (and housed their 40 guests) at its sole commercial property, the Greyfield Inn. As for their vows, JFK Jr. insisted they take place at the island’s First African Baptist Church. The owner of the Greyfield later recounted that he had shared a story with Kennedy about how the deacon of the church held an island-wide ceremony in honor of Robert F. Kennedy when he was assassinated in 1968. The story touched the younger Kennedy, and he wanted to honor the church by marrying there. The wedding took six months to plan, including the creation of Bessette’s gown, a simple, bias-cut dress designed by friend and former Calvin Klein colleague Narciso Rodriguez. It’s hard to understand if you weren’t there (kids), but this was the ultimate Nineties wedding. From Bessette-Kennedy’s understated-yet-elegant look (the simple slip dress! The bare face with a bold lip! The loose bun!) to the bare-bones candlelit chapel, it was both a time capsule and a timeless affair.

In this grand marriage of pop music and athletics, Posh and Becks tied the knot at Ireland’s Luttrellstown Castle on July 4, 1999, with only 29 guests in attendance, because they’re low-key like that. Just kidding! After two became one, they partied down with nearly 300 of their closest friends, including the Spice Girls and Elton John. For the reception, Victoria changed out of her custom six-figure Vera Wang champagne strapless wedding gown (complete with a 20-foot train … and a tiara) and joined David in donning his and hers purple numbers by designer Antonio Berardi. It was in those memorable matching lewks that they would take their rightful place on, ahem, matching gold thrones. The duo would go on to celebrate their 25^th anniversary in 2024 by posting their present-day selves in the same outfits with Victoria captioning the shoot, “Yep, still got it!” And yes, the thrones did make the grid.

It was the turn of the century, and the world was breathing a sigh of relief that Y2K hadn’t knocked our global systems offline. We rejoiced with boy-band music, butterfly clips, and a parasocial relationship with two of Hollywood’s biggest stars: box-office golden boy Brad Pitt and Rachel Green herself, Jennifer Aniston. We waited with bated breath for a wedding. We prayed Aniston would get the baby we all so desperately wanted her to desperately want. And on July 29, 2000, we got half our wish. The California-cool couple said “I do” in front of 200 friends and family members on a cliff overlooking the Pacific Ocean (in the backyard of a Malibu estate belonging to TV producer Marcy Carsey). The guest list was star-studded, and the musical lineup included Melissa Etheridge, a Greek bouzouki band (to honor Aniston’s heritage), and a 40-person gospel choir. Somewhere between the 50,000 flowers, lobster-heavy catering spread, and, yes, countless helicopters overhead (tents were erected to shield the event from photogs), the duo made it official. Until ending their union in 2005 amid rumors, well founded, that Pitt and his Mr. and Mrs. Smith co-star Angelina Jolie had started a relationship on set. Pitt would go on to make it official with Jolie in 2014, and Aniston would marry actor Justin Theroux in 2018. When both of those unions subsequently dissolved, the memory of Brad and Jen’s idyllic Malibu wedding had fans hoping for a reunion. Alas, those hopes were dashed.

On March 16, 2002, pop culture was given one of its greatest moments when multihyphenate Liza Minnelli married producer Davd Gest at New York’s Marble Collegiate Church. The two tied the knot after only a few months of knowing one another, but their wedding was an all-star affair. Minnelli’s ivory and crystal dress was designed by Bob Mackie and beloved celebrity makeup artist, the late Kevyn Aucoin, was responsible for her bridal beat. The pair were registered at Bergdorf Goodman and Tiffany & Co. Their wedding party was 36 people deep. The reception included performances from 45 acts. In other words, this thing was real. But what played out felt like scene from a David Lynch film. Minnelli had two maids of honor, one of whom was Elizabeth Taylor. Her bridesmaids included Gina Lollobrigida, Petula Clark, and Mia Farrow. (Also, singer Mya, who was only 22 at the time.) Gest’s best men were Tito and Michael Jackson. And then there was the kiss. After saying their vows, Gest planted such an aggressive smacker on Minnelli’s lips that she would later write in her memoir, “Like a shark mangling a piece of meat. Ugh! I felt degraded.” It’s no wonder the two parted ways in 2003 (though their contentious divorce would go on four more years). Now, all that’s left are memories and that iconic photo of the happy couple flanked by Elizabeth Taylor and Michael Jackson.

While many remember Pamela Anderson’s iconic bikini-clad wedding to Tommy Lee (held on a beach in Mexico just 96 hours after meeting), her marriage to Kid Rock was equally unhinged (and underdressed). First linked to one another in 2001, the pair were engaged in 2002, only to call things off in 2003. But they fell back into each other’s arms in July of 2006. Later that month (yes, we said month) the couple were married on a yacht in St. Tropez. The groom wore a fedora (not a shirt) and the bride wore … another bikini. On Aug. 2, the pair had a legally binding (and clothed — we hope?) ceremony at the Beverly Hills Courthouse. Shortly thereafter, on Aug. 17, the pair took the stage at Nashville’s Tootsie’s Orchid Lounge honky tonk (she in a white Juicy Couture tracksuit, he in his signature white tank) to say “I do” yet again, before Kid Rock serenaded his bride with “Some Kind of Wonderful.” Unfortunately, the third time was not the charm. Anderson filed for divorce on Nov. 27 of that year, with her rep noting, “It was not a happy Thanksgiving.”

Little did we all know that on April 4, 2008, music’s royal couple said “I do” in New York City. The music moguls are famously private about their private life, and their wedding was no exception. In fact, they held the intimate gathering at home, a.k.a. Jay-Z’s 13,500-square-foot penthouse in TriBeCa. Intimate doesn’t always mean small, though. The 3,000-square-foot living room (where the ceremony took place) was covered in a tent filled with flowers, candles, branches, and crystal icicles to create a winter wonderland theme. The couple also had 70,000 white dendrobium orchids flown in from Thailand. Beyoncé wore a gown designed by her mom, Tina Knowles, and the 40 guests included her Destiny’s Child bandmates, as well as Gwenyth Paltrow and Chris Martin. Phones were collected as attendees arrived, so that no pictures could be leaked. And it worked! None of us knew the two were hitched until 2011, when Bey revealed her wedding dress in a video for Live at Roseland. Three years later, Jay-Z included clips of their ceremony during the pair’s joint On the Run tour.

After a whirlwind six-week romance, the singer and the comedian made their are-they-or-aren’t-they relationship official with a surprise wedding on April 30, 2008. Held at Carey’s private Bahamian estate, the nuptials were a complete shock to the dozen guests who had been flown in for what they thought was a music video shoot. The two wed at sunset on the beach, with Carey donning a simple white Nile Cmylo slip dress and Cannon in a Balenciaga tuxedo. Later, they joined their guests for a lobster feast which they washed down with bottles of Dom Pérignon. Carey, who famously loves an anniversary, found a soulmate in Cannon: The two renewed their vows every year after (until their 2016 divorce), including in a ceremony officiated by Rev. Al Sharpton, at the Eiffel Tower in Paris, and at Disneyland (they had the park closed for the occasion), where they dressed as a prince and princess.

Custom designer gowns! Historically significant venues! An E! camera crew! Kim and Kanye’s wedding had all the makings of a modern-day fairy tale. Planned almost entirely by West, the multiday event spanned two countries and two chartered planes. Two hundred guests were invited to the rehearsal dinner, for which West rented out all of the Palace of Versailles. Like, the whole thing. Dinner was served in the palace’s Hall of Mirrors, where everyone enjoyed a surprise performance from Lana del Rey. The next day, the whole gang was flown to Florence to watch Kim and Kanye exchange vows at Forte di Belvedere. Kim walked down the aisle in a custom lace Givenchy gown designed by Riccardo Tisci, estimated to have cost about $500,000. (The couple’s 11-month-old daughter North also wore Givenchy.) She was escorted by Caitlin Jenner, while being serenaded by Andrea Bocelli, which would later give us the iconic scene from The Kardashians in which Kim and Kourtney are feuding about the latter’s choice to marry Blink-182 drummer Travis Barker in Italy with a performance by the same Italian tenor in 2022, in which Kim declared: “Who performed at my wedding? Andrea Bocelli. Who performed at Kourtney’s wedding? Andrea Bocelli. You stole my fucking wedding country and my wedding performer.”

America’s sweethearts wed in Venice, Italy, on June 27, 2025, after a lavish three-day celebration fit for George and Amal Clooney. (No, seriously, it was basically an Amazon dupe of the A-listers’ own three-day Venetian nuptials.) On the big day, the bride wore a corseted, mermaid-style wedding dress custom-designed by Dolce & Gabbana, featuring hand-appliquéd Italian lace and 180 silk chiffon-covered buttons. The gown was inspired by one worn by Sophia Loren in the 1958 film Houseboat. (Sanchez told Vogue ahead of her wedding that the look was more modest than her usual style, saying, “It is a departure from what people expect.”) The wedding, which was rumored to have cost around $55 million, saw its share of celeb guests, including Oprah, most of the Kar-Jenners (suddenly Kim was cool with someone stealing her wedding country), and climate-change activist and actor Leonardo DiCaprio. We continue to wish the couple our best and many happy (free) returns.