Pop star who bought the Best Picture Oscar for "Gone with the Wind" :

Michael Jackson
Jackson paid $1.54 million in 1999.
Source: Los Angeles Times, 3/3/2006

 
   
  Celebrity who purchased two of Bette Davis's Oscars:

Steven Spielberg
Spielberg bought Davis's Oscars, for "Jezebel" (1938) and "Dangerous" (1935), with the intention of returning them to the Academy. He also bought Clark Gable's Oscar for "It Happened One Night" for the same reason.
Source: Toronto Sun, 12/20/2002

 
   
  Website that is paying $30,000 a year to lease an Oscar:

Goldenpalace.com
The online casino is leasing the Oscar from the estate of Morris Stoloff, who won for Best Musical Score for 1960's "Song Without End." The lease agreement extends for the next 999 years.
Source: Los Angeles Times, 3/3/2006

 
   
  Celebrity who bought the Oscar awarded to the director of "Casablanca":

David Copperfield
Copperfield bought the Best Director statuette originally awarded to Michael Curtiz for $231,500 in 2003.
Source: Washington Post, 11/22/2003