One-time defense contractor David Brooks dropped $10 million on his daughter's bar mitzvah in 2005. Brooks paid for a variety act that reportedly included Nelly, 50 Cent, Ciara, Tom Petty and Aerosmith. Party favors for the kids included iPods and digital cameras. Brooks would later be convicted on 17 criminal charges for tax and securities fraud, 14 of which he still contests.
NEXT: Roger McNamee, 2006