Sean Penn‘s directing career is not a happy one. Which is to say that the films he makes are not happy. At all.

Consider all four of em: The Indian Runner, The Crossing Guard, The Pledge and Into The Wild. The first about two brothers who cannot reconcile their differences, the second about a father out to kill the man who killed his young daughter, the third about a grizzled cop obsessed with catchting the killer of a child and the fourth about a young man – a child in many ways – dying alone in the wilderness.

Death and the difficulty of doing good are the central themes of Penn films, making his next film’s title – The Comedian – all the more intriguing. And then there’s the cast. Robert De Niro and uber-comedian Kristen Wiig have joined to the project, working from a script by accomplished producer Art Linson and Jeffrey Ross [Deadline]. De Niro and Penn both starred in Art Linson’s autobiographical What Just Happened, directed by barry Levinson.

De Niro will play Jackie Burke, a former star comedian attempting to capitalize on his past television fame and rejuvenate a non-existent career. After being sentenced to community service, he meets a woman named Harmony (presumably Wiig) who turns his life around. It sounds a bit hopeful for Penn, especially that “turning his life around” bit. But hey, the guy’s getting older and maybe a bit softer?

Wiig has proved herself in dramatic fare (see All Good Things) and De Niro needs to remind people he still cares about acting.

What do you think of Sean Penn as a director? Do you like his films?

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