(2003) Already divorced and in analysis at 21, Jerry Falk (Jason Biggs), an up-and-coming comedy writer - who also serves as narrator - gets advice from a 60-year-old public-school teacher, David Dobel (Woody Allen, who wrote and directed this romcom), who's "too frightened to give up his job and try comedy full-time." David tells the younger man jokes to sum up "the great whatever."
When Jerry reveals his larger ambition - "I want to write a novel. A novel about man's fate in the empty universe. No God, no hope, just human suffering and loneliness" - Dobel recommends: "I would stick to the jokes - that's where the money is." Dobel then relates an experience of once pouring his heart out to a cab driver "about all the stuff you were prattling on about - life, death, the empty universe, the meaning of existence, human suffering - and the cab driver said to me: 'You know, it's like anything else.' Think about that."
But Jerry has his thoughts all tangled up in his girlfriend Amanda Chase (Christina Ricci, with big eyes and round face like Peter Lorre but sexy), an aspiring actress and singer who's often late and disorganized and difficult. In addition to her smoking cigarettes and taking sleeping and diet pills (saying she's fat, though she's not at all) and not feeling like having sex for the past six months (though she assures him it's okay for him to have sex with other women), her mother Paula (Stockard Channing) has come to live with them in their Manhattan apartment.
She assures Jerry that both her mother's staying (Paula, wanting to relive her youth by developing a cabaret act, requests help from Jerry for humorous dialogue while snapping at him when he calls her "Mrs Chase") and her lack of lovemaking will be temporary.
Flashing back to first meeting Amanda, when Jerry was with Brooke (KaDee Strickland) and she was with Bob (Jimmy Fallon), he recalls how they both admitted to experiencing an immediate, fatal crush on each other. "Don't give me that!" screamed Brooke in their breakup: "I don't believe you! Those marks on your back are bite marks! You think I believe you fell on your comb?!"
Along with informing Jerry that his "loving-disabled sex kitten" is cheating on him and urging Jerry to team up with him as comedy writers for a TV show in LA, Dobel ("a deeply deranged human being" paranoid of anti-Semites with a gun in every room of his residence) insists on buying a Russian rifle for his protégé for self-defense and assembling a survival kit - "There were actually groups in Germany called 'Jews for Hitler.' They were deluded.… They trusted a naked bus driver. Never trust a naked bus driver" - which incites domestic strife when Amanda and Paula return to the apartment.
Danny DeVito plays Jerry's loser talent agent Harvey Wexler with only one client; jazz singer Diana Krall performs; Erica Leerhsen appears as Connie, a friend Amanda introduces to Jerry.
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