Answers revealed in the comments.
GAME 1
Since 2000, there are four MLB managers who have lost the World Series at least twice. Name two of those four managers.
GAME 2
In his four highest-grossing films at the U.S. box office, what actor has played or voiced characters named King Louie, William Cleary, Frank Abagnale Sr., and Max Shreck?
hebspeaks 
Game one answers:
Dave Roberts
Jim Leyland
Ron Washington
Joe Torre
Game two answer: Christopher Walken