6. Kiss Kiss Bang Bang: This 2005 action comedy had Downey playing a thief masquerading as an actor. Downey’s character, Harry Lockhart, gets entangled in a murder mystery that also involved Val Kilmer as a private investigator and Michelle Monaghan as Harry’s childhood crush, Harmony. She thinks Harry is really a PI and hires him to investigate her sister’s suicide, which she thinks she was a murder. Downey and Kilmer make a bang-up comedic duo as they flail about in an effort to learn the truth about Harmony’s sister’s death. Downey’s performance got rave reviews and though it was a limited release in the US, Downey fans (myself included) undoubtedly enjoyed his signature quirkiness in the film.
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