This is Chris Rock's version of Woody Allen's "Stardust Memories". He asks the same question. "What happens when a comedian wants to be taken seriously?" Unfortunately this film comes off smug and self indulgent. You never get the sense there is any acting going on.
Mr. Rock makes great use of New York City as a backdrop and has a fine time casting his famous friends in cameos but it all seems worthless. Just watching him go about his daily business, complaining to a NY Times reporter, "played" by Rosario Dawson isn't enough to be satisfying to the viewer. I enjoy Mr. Rock as a stand-up comedian but as a filmmaker, he has yet to really make an impact. I'm sure his real legion of fans will consider this film his "Citizen Kane", a great leap forward in his career but they will be blinded by their loyalty.
All the good jokes are in the trailer and fall flat if you already know them. The film is far from "hilarious" and only at times mildly amusing. Mr. Rock's outcome with Ms. Dawson is inevitable and even the twist is pretty obvious. I will admit his satirical portrait of reality stars does hit the mark and is the smartest thing about the film. Gabrielle Union is actually very good as the reality star fiancee to Mr. Rock's character and she nails her one scene of honest emotion.
I give Mr. Rock credit for examining his life at this apparent crossroad of his career but I don't need to pay to watch him work out his therapy on screen. And what Top Five rap list is complete without KRS-One?