The Grand (Zak Penn, 2008) 
Penn's mockumentary of the world of high stakes poker suffers from a few problems. One, a cast full of funny people improving doesn't necessarily mean a funny movie. Two, the film suffers from having come two or three years too late to catch the poker boom. Third and perhaps most, the film suffers from the Christopher Guest effect; if every film of this type is going to be compared to Guest's films, it clearly pales in comparison. Fair or not, The Grand isn't consistent enough in its humor to really be considered much more than a Guest knockoff. The plot centers around Jack Faro (Woody Harrleson), just out of rehab, as he enters The Grand Championship of Poker in order to save his grandfather's casino to a egotistical developer (Michael McKean doing a crummy Trump variation). That serves as a springboard to be able to introduce a parade of characters, all interpretations of the various personalities televised poker has presented over the years. The problem here is that for those who have never watched poker, they'll wonder why some of these people act the way they do and those who know will find some of the characters to be weak imitations of real people who aren't that interesting to begin with. Faro is the only one who doesn't fall into a ready-made persona but he's the character who gets too few of the laughs. All the others have one or two funny moments but it's only Chris Parnell as a socially stunted math genius and Richard Kind playing the clueless amateur that bring any consistent laughs out of the film, mostly because they stretch the limits of their characters. David Cross and Cheryl Hines, on the other hand, fail a bit because they play characters like the real people at these events who are unlikable in the first place. And not that funny. The poker action is without much tension and too staged to advance the plot to really make it believable. If this film has just gone out there and become surreal and bizarre (as some brief instances of Werner Herzog's character bring out), it may have not turned into such a bore.