Jonathan Ames (Jason Schwartzman), a struggling Brooklyn writer with a drinking problem, tries to cope with his recent breakup with his girlfriend by reinventing his life.

On a whim, Ames decides to emulate his idol novelists Dashiell Hammett and Raymond Chandler by posing as a private detective and offering his services through an online ad.

Soon enough, he takes on various cases of unwitting clients, satisfying some while failing others.