Days before Christmas, the Material Girl spared no expense for her second wedding -- to British director Guy Ritchie -- on Dec. 22, 2000, in Scotland. At the 19th-century Skibo Castle, the couple booked all of the rooms on the 7,000-acre estate for their guests: Gwyneth Paltrow, Brad Pitt, George Clooney, Trudie Styler and Sting, to name a few. Madge wore a strapless cream Stella McCartney gown and a 1910 gold and diamond-encrusted tiara (that once graced the head of Monaco’sPrincess Grace); her 27-carat diamond cross necklace was a Harry Winston loner. Ritchie wore a kilt, as did the couple’s infant son, Rocco. (The couple divorced in 2009).