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Glenne Headly makes her first appearance as Karen Stottlemeyer, the woman whom Captain Stottlemeyer (Ted Levine) disdainfully dismisses as "my hippie wife." While filming a documentary about Miles Holling (Patrick Cranshaw), the world's oldest man, Karen is thrown for a loss when Holling dies in bed. Though her husband is certain that Holling succumbed to natural causes (he was, after all, just one day shy of his 115th birthday!), Karen is convinced that the man was murdered--and she wants Monk (Tony Shalhoub) to prove it. In the course of his investigation, Monk uncovers a surprising link between Holling's death and a hit-and-run fatality that occurred five years earlier--the only unsolved case in Captain Stottlemeyer's career.