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Mariah Carey and Tommy Mottola
Estimated Cost: $500,000
The Wedding: The songstress wed her mentor in 1993 at New York's St. Thomas Episcopal Church before 300 guests, including Bruce Springsteen, Barbra Streisand and Billy Joel. The couple split in 1996 and divorced two years later.
Most Outlandish Detail: Carey's Vera Wang gown — complete with a 27-foot-long train — cost $25,000.