Larry and Jeff invest in a restaurant with actor Ted Danson. In lieu of attending his dentist's dinner party, Larry decides to shop for waiters' uniforms, and in the process buys matching shirts for Ted and himself. But after Danson realizes his shirt has a small rip in it, he demotes Larry in The Wizard of Oz scene they're re-enacting for his daughter's birthday party (Larry refuses to switch from the Lion to the Tin Man). At the party, little Jill Danson misses the piÃ±ata and hits Larry in the mouth with her bat. Following an emergency visit to his dentist (who learned why Larry had skipped the dinner party), Larry is left with two abnormally large front teeth and one clean shirt that both he and Ted covet.
Nearly five years after the rest of the world, Larry discovers cell phones. Using his new toy, he calls Cheryl and asks her to tell Randy, the chef at Larry's new restaurant, to omit peanuts from the dinner that night because Richard Lewis's girlfriend Deborah is allergic to them. But bad phone reception prevents Cheryl from hearing the message, and Deborah gets sick. A practicing Christian Scientist, Deborah refuses to take medicine to clear up the hives on her face. Richard will not be seen with her at the Emmy Awards that night, so he and Larry concoct a plan to bake a batch of Benadryl-laced brownies for Deborah to eat. The ruse fails, and that night on national TV, the Davids see Joan Rivers lambasting Richard and his none-too-attractive date on the red carpet.
Dismayed in part over the peanut incident, Randy quits his job at the restaurant, and Larry, Jeff and Ted must search for a new chef. Ted suggests they audition his personal chef, but at dinner Larry feels the food “”just wasn't that good“” and rejects the candidate. Meanwhile, Larry accuses his wife Cheryl of having a crush on a tennis-playing cast member of “”Tony & Tina's Wedding“”; a couple refuse Larry's wedding gift because it's more than a year late; and a saleswoman becomes convinced that Larry is stalking her as revenge for her being too aggressive.
Larry, Cheryl, Jeff and Susie encounter a “”nanny from hell“” whose reign of terror is thwarted by ten sponge cakes. Larry commits a “”penis faux pas“” after a pool party, and Richard Lewis seeks immortality from Bartlett's Quotations.
A rumored threat of a terrorist attack undermines a benefit performance by Alanis Morissette at the home of one of Larry's friends. Meanwhile, Larry can't help snubbing Mindy Reiser, wife of actor Paul Reiser, during a series of encounters at a restaurant and the perfume shop where she works.
Larry's mother dies while he's shooting a film in New York City, but he doesn't find out until he returns to Los Angeles two days after the funeral. Once he's past the initial shock, Larry uses his loss as an excuse to avoid a number of unsavory invitations. Meanwhile, Richard Lewis accuses Larry of taking back his meditation mantra, and Larry plots to relocate his mother's body at the cemetery.
Over a makeup dinner with the Braudys, Larry openly ponders the question, “”When a husband pays the check, do you have to also thank the wife?“” Meanwhile, Jeff's return home is ruined by his allergy to the family's corpse-sniffing German Shepherdâ€”but his daughter Sammy refuses to give away the dog. Concerned about his agent's welfare, Larry figures out an ingenious way to give the pooch to the Braudys, who are looking for just such a dog.
Larry is accused of betraying the confidences of Wanda's boyfriend, Crazy-Eyez Killa, a rapper he met at a party. Later, Larry alienates Jeff's wife Susie by declining her house-tour offer. He encounters further problems when he tries to replace a sports jacket Cheryl threw out.
Larry proves himself an unskilled Christmas tipper, while both Larry and Jeff prove incompetent at creating believable alibis for the messes they get in. After offending his housekeeper, Larry makes amends with her at the expense of his wife. Later, Larry attempts to reconcile with Cheryl's family after ruining their nativity scene.
Larry figures out a way to fire a chef, and alienate an important restaurant critic, in the days before his new restaurant is scheduled to open. As Susie stews over a misunderstanding with Larry and Cheryl, the Davids spend some quality time at the car wash. With its grand opening at hand, the restaurant owners hire a new chef with a penchant for speaking his mind.