Season 6, Episode 2 "Mr. Monk and the Rapper": Monk, in a nervous stupor, agrees to help a rapper accused of murdering a rival. The problem is, Monk thinks he might have done it.
Monk (Tony Shalhoub) unknowingly spends his final moments with his loving wife, Trudy (Melora Hardin), before her tragic and mysterious death. (Season 8, Episode 15)