Sean Connery — Said No to Gandalf ($450M)

Sean Connery's decision to pass on playing Gandalf in *The Lord of the Rings* trilogy is the single largest financial rejection in cinema history. Peter Jackson offered Connery 15% of the box office gross, which, with the trilogy earning $2.99 billion, means Connery left approximately $450 million on the table. Connery said he "didn't understand the material," a claim that seems almost unfathomable given Ian McKellen's definitive, generation-defining performance. This amount is $160 million more than the $290 million #3 Matt Damon rejected from *Avatar*, cementing it as the most expensive "no" ever. Connery retired in 2003, and one can't help but wonder if passing on half a billion dollars hastened that decision.