Sir Philip Green
50th birthday, 2002; 55th birthday, 2007: To mark turning 50, the British retailing billionaire flew 200 guests to Cyprus for a three-day, $7.1 million toga party featuring a massive Buddha sculpture and the song stylings of Jennifer Lopez. Five years later, he spent $10 million on a five-day extravaganza in the Maldives.
50th birthday, 2004: The five-day, $4 million celebration began with a 70-person dinner atop Chicago's then-named Sears Tower before moving west for a luncheon at L.A.'s Hotel Bel-Air. (Maya Angelou wrote a poem for the occasion.) Dinner featured a 23-karat-gold gilded cake.
50th birthday, 2009: The American Idol judge hired a fleet of limos to drive 400 guests to Wrotham Park, a 250-year-old estate outside London. The $1.5 million party, organized by friend and fellow birthday enthusiast Sir Philip Green, featured pictures of Cowell in the toilet stalls.
60th birthday, 2002: The TPG Capital co-founder whisked 500 guests to the Hard Rock Hotel and Casino in Las Vegas for private concerts by John Mellencamp and the Rolling Stones. Robin Williams entertained during dinner. The bill: $7 million.
70th birthday, 1989: The late publishing and real estate magnate spent $2 million to fly nearly 800 guests—Barbara Walters and Henry Kissinger, included—to Tangiers for a three-day blowout hosted by Cleopatra herself, Elizabeth Taylor.