Phil (Greg Kinnear), a depressed dentist, hates his life and wants to commit suicide. While stalking one of his seemingly happy patients, Michael (Bradley Whitford), he sees him committing suicide. He then convinces his widow, Alicia (Emily Mortimer), that he's Michael's old Greek friend, Spiros, to try find out what made Michael so unexpectedly unhappy. Even Michael's father (Robert Forster) falls for his scheme.

      Phil has a concept that could have worked as a screwball comedy, but it takes itself too seriously to be funny and the vast majority of the attempts at humor fall flat. Comedy, after all, is almost always grounded in tragedy. If the plot were more plausible and less contrived, it could've worked as an interesting psychological thriller or as a character study or both. The screenplay by Stephen Mazur is clunky, uneven in tone and requires too much suspension of disbelief as soon as Phil begins his con. There are so many plot holes, especially during the third act that feels rushed and leaves too many plot holes behind, i.e. why wasn't Phil charged with fraud? He's a criminal albeit a very emotionally unstable one that needs therapy. What was Phil's childhood like? What was the relationship like with him and his parents? There's very little about Phil or any of the other characters that rings true. It's ok that he's unlikable and flawed because all human beings have flaws and some of the most interesting characters in cinema are unlikable, but Phil never really comes to life.

      Greg Kinnear played a depressed man before in As Good as It Gets, and that character, Simon, is much more true-to-life and well-written character than Phil. Mazur co-wrote a far superior movie about con artists called Heartbreakers which also was far from realistic, but at least its screenplay is witty and often hilarious. Liar Liar is very funny and witty as well. Both of those films are still entertaining and funny no matter how many times you watch them, so Phil is an anomaly for the talented Mazur. Hopefully Greg Kinnear, who's a first-time director, will work with a better screenplay next time around. To be fair, no director could've improved the film without completely re-writing the screenplay because its issues are systemic, not systematic. Phil is a misfire that overstays its welcome at 1 hour and 46 minutes. Even the charismatic Kinnear, who also directs the film, can't rise above its inane screenplay. It's just as disappointing as the unfunny 80's comedy, The Lonely Guy, starring Steve Martin.