The Jamie Kennedy Experiment

As a flamboyant casting director, Jamie auditions an actor who's made an indecent proposal by the (considerably older) casting assistant; Jamie appears on a phony dating show (hosted by Whose Line's Jeff Davis) as a meek geek who still lives with his parents; at a funeral, Jamie tries to steal a valuable ring... from the guest of honor, who's wearing it, enlisting the aid of an innocent bystander.