In the season 2 episode "Mr. Monk and the Very Very Old Man", Karen has to beg Leland to investigate the murder of Miles Holling, the world's oldest man (115 years of age). Leland promises to her that he will investigate if Monk believes that there has been foul play in Miles' death. Because Leland never watched her documentary "Miles Holling: The Human Time Machine", Karen kicks him out of the house and Leland is forced to temporarily room with Monk. He does eventually watch the film, which gives him a clue needed to solve both this case and a hit-and-run from several years earlier.