There was little doubt Prince Harry would be the best man at his brother's wedding to Kate Middleton, but the House of Windsor did have concerns about the bachelor party he might throw. Though early reports about this weekend's stag events appear to be relatively tame, in 2008 the princes hosted a rowdy, two-day bachelor weekend for their cousin Peter Phillips that included drinking games, a pub crawl, and matching black rugby shirts for the entire wedding posse. "They also had this beer funnel that they kept passing around," one bar manager recalled. "It makes you drink a pint of beer in about two seconds and pretty much everyone in the pub had a go on it by the end of the night." In other words, everyone was royally smashed.
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Actor Richard Kind has been one of George Clooney's best friends since they played siblings on The Bennett Brothers, a little-seen TV pilot in the late '80s. He's also been a favorite target of Clooney's legendary pranks—the Oscar-winning actor once found a painting in the trash, signed it, convinced Kind he was taking art classes, and got his pal to hang it in his home. In 1999, the former Spin City star tapped his old roommate (Clooney also once left a special present in Kind's cat litter box) to be best man at his wedding to Dana Stanley—although Philadelphia magazine later questioned the "wisdom of having the Sexiest Man Alive stand next to you at the altar."
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When music producer David Gest married Liza Minnelli in 2002, he asked Michael Jackson to be his best man. It made perfect sense: The two had known one another since they were teenagers, and Jackson was also close friends with Minnelli's maid of honor, Elizabeth Taylor. Considered one of the most expensive weddings of all time—the affair cost an estimated $3.5 million, featured a 60-piece orchestra with Tony Bennett performing, and each of the 1,500 guests received a satin candy box embroidered with the words "Liza and David 4 Ever." The couple divorced the next year, and Minnelli later blamed Jackson for letting her marry an "idiot."
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Steve Martin has guest hosted Saturday Night Live more than anyone else, and when he wed former New Yorker staffer Anne Stringfield in July 2007, it was SNL creator Lorne Michaels who stood by his side. The ceremony, which took place at Martin's Los Angeles home, was presided over by former Nebraska Senator Bob Kerrey and the guests included Tom Hanks, Michael Douglas, Diane Keaton, and Carl Reiner. Recently, Michaels also played a crucial role in getting famous musicians to play on Martin's latest CD, Rare Bird Alert. As the comedian told David Letterman: "He said to me one day, 'You don't use your friends enough.' I then began a most convoluted search for a contact number for Sir Paul [McCartney], whom I had met briefly only twice, but then conveniently counted among my closest friends."
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The men in pinstripes have been best friends since 1995, when they entered the big leagues together. In late 1999 and early 2000, the Yankee shortstop also served as best man at Posada's wedding double-header. The first ceremony was a four-person affair at home—the couple shared pizza but didn't have rings. A few months later, the Posadas had a proper celebration in Puerto Rico, and Jeter stood by his catcher once again. Perhaps Posada can return the favor if Jeter ever proposes to Minka Kelly, his girlfriend of three years.
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Shortly after Ronald Reagan proposed to actress Nancy Davis at Los Angeles' legendary Chasen's restaurant in 1952, the couple exchanged vows at the Little Brown Church in Studio City. The private ceremony was attended by only two guests: actor William Holden and his wife, Ardis, who served as best man and the matron of honor. Afterward, the Reagans went back to the Holdens' home to cut their cake, before spending their wedding night at the historic Mission Inn in Riverside, California. The hotel still features "The Great American Package" in honor of the late president.
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When you ask Elton John to be the best man at your wedding, it comes with the built-in possibility of having him sing at your reception. And that's exactly what happened in 2007, when actress Elizabeth Hurley wed Indian millionaire Arun Nayar. The elaborate, weeklong affair began with an Anglican ceremony at a 15th-century castle in Gloucestershire (where John walked Hurley down the aisle and Patsy Kensit gave a Bible reading) and continued at Umaid Bhawan Palace in Jodhpur, India, for a full Bollywood blowout that lasted three days. The marriage, however, only lasted three years—Hurley announced she was getting a divorce in December 2010.
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Actor and author Stephen Fry is apparently such a good friend that both Hugh Laurie and Rowan Atkinson requested him as the best man at their weddings. In his toast for Atkinson, Fry described his Blackadder co-star, saying: "It is as if God had an extra jar of comic talent and, for a joke, gave it to a nerdy, anoraked northern chemist." But apparently Fry performed his best-man duties well—each man is still married after more than 20 years.
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NASCAR driver Kyle Busch certainly went the extra mile for a fan in 2009. Damon Landry had planned to marry Heather Wilson in Victory Lane at the Las Vegas Motor Speedway, but he didn't have a best man and there was a press conference scheduled to take place during his ceremony. Enter Busch, who had just won the pole at the Shelby 427 and solved both problems at once. Still in his fire suit, Busch took off his baseball cap, handed Landry the ring, and posed for photographers as the couple exchanged vows. After the ceremony, Busch gave the Landrys a gift from one of his sponsors—several bags of M&Ms.
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The interracial marriage of Sammy Davis Jr. and Swedish actress May Britt was so controversial that he received death threats. It even affected the 1960 presidential election. Davis' longtime friend Frank Sinatra was set to be the best man at the October 1960 wedding, but the Kennedy campaign was concerned that his role would hurt JFK at the polls due to his friendship with the singer. In the end, the ceremony was postponed until after Election Day and Sinatra remained best man. But the bride almost didn't make it down the aisle—she got an intestinal virus shortly before the service. "I was a little woozy," Britt later admitted to Life magazine, "but I was able to get through with it because of the excitement of marrying the man I love." And JFK's sister, who was in attendance, asked the groom, "How do you feel, Chicky Baby?" Davis replied, "Man, I'm electric!"
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"I think Howard Hughes and I were friends because he didn't want anything from me and I didn't want anything from him," Cary Grant said of his close relationship with the enigmatic billionaire. But that wasn't quite sincere. Grant liked keeping company with Hughes' wealthy friends and Hughes enjoyed meeting actresses that Grant knew. (It was Grant who introduced Hughes to one of the loves of his life, Katharine Hepburn.) In 1948, Grant, then 44, fell for 25-year-old Betsy Drake, with whom he would later co-star in Every Girl Should Be Married. On Christmas Day the next year, Grant backed that up by marrying Drake at his best man Howard Hughes' ranch in Arizona. When the ceremony was finished, Hughes personally flew the newlyweds back to Los Angeles and drove them home, where his wedding present was waiting—a white poodle that Drake named Suzie.
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When 43-year-old Idi Amin married his fifth wife, an 18-year-old former go-go dancer, in a private ceremony in July 1975, the Ugandan dictator was concerned that he had prevented his people from sharing in his blessed day. So he held a lavish second ceremony—reported to have cost £2 million ($3.2 million)—that was televised. PLO leader Yasir Arafat served as Amin's best man and the groom cut the cake with a sword. Though Amin fled his country in 1979, Uganda's connection to Arafat remained strong. When the Palestinian president was near death in 2004, Uganda's deputy prime minister called on the nation to pray for the former best man's health.
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