Made with five Wilson family members, the rambling story follows fictional good-hearted Texas criminal Wendell Baker (Luke Wilson), whose extended prison sentence for selling counterfeit driver's licenses to Mexican immigrants motivates him to pursue hotel management. Still heartbroken at the loss of his true love Doreen (Eva Mendes), Wendell takes an administrative post at Shady Grove, a shabby retirement hotel overseen by a couple of con men nurses running a perplexing Medicare scam. Wendell's fast friendship with a crew of quirky residents, played by Harry Dean Stanton, Seymour Cassel and Kris Kristofferson, results in a last-ditch attempt to steal Doreen away from the grubby hands of her grocery store manager husband Dave Bix (Will Ferrell).
It's evident by the incremental narrative skids that come with the passing of each of its three acts that Luke Wilson started out with an energized idea that he simply couldn't sustain. In spite of Eva Mendes' absent romantic chemistry, we get swept up in Wilson's easygoing charisma as a con-man social activist.
Wendell compares the Rio Grande to the Tigris River as he and his partner-in-crime Reyes (Jacob Vargas) set up their mobile shop to sell phony IDs to illegal migrant workers. Wendell is a yammer, and he takes pride in spinning a yarn about all of the famous Latinos he has supposedly made friends with over the course of his long career in forgery.
After being arrested and sent to the big house, Wendell brokers an off-screen truce between penitentiary gangs of Crips and Skinheads that's funny for its droll implications, but the humor evaporates too soon because we don't get to watch him do it. Luke Wilson takes an anti-Woody Allen approach to writing and connecting scenes. He's not confident enough as a screenwriter or as a comedian to put his neck on the line for a laugh.
Wilson co-directed the movie with his older brother Andrew -- both are making their directorial debut here -- and the diluted effort shows strain just when the movie should hit its stride. After getting a somewhat belated discharge because of his cheesy demeanor toward the parole board, Wendell takes to his new job at Shady Grove like a fish to water. Standing in the way of his envisioned glory is head nurse Neil King (Owen Wilson) and his lackey sidekick McTeague (Eddie Griffin in a futile role). Neil revels in being snarky to Wendell and to the hotel's vulnerable tenants. He's set up to be a proper antagonist but the character all but falls off the radar after making a few derogatory comments and hinting at his corrupt plans.
The humor spikes briefly during fiery altercations between Wendell and Will Ferrell's Dave Bix. Ferrell reaffirms his exemplary supporting-role skills during episodes of physical comedy where Wendell and Bix fight and threaten one another in full-on junior high school fashion. Still, you can recognize Wilson's shyness about pushing the parody too far. In a '70s-era Allen movie (think Play It Again Sam), Dave would have been named "Dick" Bix and the subplot would have played into the ending of the story.
The Wendell Baker Story comes to gravitate around aging rest-home inhabitants Skip (Dean Stanton), Boyd (Cassel) and Nasher (Kristofferson), all of whom dream of one last sensual encounter with the fairer sex. But that possibility appears less probable for the reclusive Nasher who looks barely alive above the neck. Nurse Neil plans on shipping the three old codgers away so he can collect their medical stipends, and it's here that Wendell comes to the rescue by association since Skip and Boyd take an active interest in reuniting him with Doreen.
The money scene of the movie comes when Skip and Boyd try to pick up a couple of young women working at a convenience store. Stanton and Cassel pour on the charm and the actors' real-life friendship of 40 years spices the episode with a texture of lively improvisation. These two highly accomplished actors could command their own movie alone -- The Ballad of Skip and Boyd. Now there's a sustainable idea for a movie. Grade: C-