Connect the celebrity
The way to play this game is in the fashion of 7 degrees of Kevin bacon. The way we do it is, each person names one celebrity that connects us to the final celebrity.
So if I say, we are going to connect Sandra Bullock and Drew Barrymore, one person would say:
Sandra Bullock played with Aiden Quinn in Practical Magic.
Then the next poster would say: Aiden Quinn played with Brad Pitt in Legends of the Fall
Next poster: Brad Pitt played with Tom Cruise in Interview with a Vampire...
And so on until we get to the final celebrity, then the next person gets to name the next two celebrities to connect.
Here is the first connection: Sean Connery to Robert De Niro
Sean Connery played with Nicholas Cage in 'The Rock'