While getting Oscar ready for school, Porter is blindsided by the unexpected arrival of his football player brother and certainly unprepared to tackle the concept that Bobby's new million-dollar contract requires him to move into Porter' responsible household. An immediate clash of lifestyles and philosophies winds Porter up in hospital getting a marble removed from his nose (by a pretty nurse whom Bobby encourages him to ask out), then back in hospital after an inadvertent barroom brawl (while a reluctant Dena babysits Oscar). But it all loosens Porter up to the point where he can tell Oscar next morning that they are playing hookey and going to the zoo together, and that he has a date with the nurse.
After taking Uncle Bobby's advice to make his fellow student's laugh in order to be more accepted among them, Oscar ends up in the vice-principal's office. But it's Porter and Bobby who are punished when the vice principal sees that Oscar is being brought up by two very different personalities, and sends them to a parenting class prompting Porter to teach Bobby a lesson by letting him take the responsibility of being ""Oscar's dad"" for a few days.
Porter's worried about Bobby's influence when Oscar decides he wants to be a bus driver instead of going to college. Since Oscar's been spending so much time with Bobby, Porter's has been left with gaps in his day. So Bobby suggests he get a hobby and he tries his hand at falconry. This episode introduces the recurring characters of Rose, Oscar's classmate, and her carpool driving single mom Marilyn.
When Oscar and Rose are allowed to go to the movies by themselves, Rose persuades Oscar to sneak into an extra film without paying; and when Oscar inadvertently confesses, Porter decides to teach his son a lesson and returns him to the scene of the crime where the manager has the boy arrested and charged. Following Dena's advice, Porter visits the district attorney to plea bargain, but is appalled when Bobby tries to bribe the official, who ultimately agrees to drop charges only because he is a fan of Bobby's. Porter is left fulminating about the importance of honesty to an empty room when the others all go off to sneak into the movies, but his tirade gets recycled by Bobby at a dinner speaking engagement he has refused to prepare for.
When Porter berates Bobby for not cleaning up after himself, Bobby reacts in a typical fashion: he hires a maid. This is not the lesson Porter had in mind, so he winds up doing all the work while the maid watches soap operas; but this is not the lesson he intended either.
An unusually clever Halloween episode that actually makes a point about the impact of Halloween scares on very young children while cleverly poking fun at the structural games of recent horror films. Bobby's gross costume frightens Oscar more than he wants to let on, ruining his favorite holiday of the year, and Porter's anger is partly directed at the sadistic pranks Bobby used to play on him as a child. But when Bobby tries to comfort Oscar after a particularly bad nightmare, everyone finds themselves trapped in a series of Chinese box nightmares as each character in turn wakes out of the previous character's dream. Ultimately Porter takes Oscar to see a psychologist friend, who just happens to be costumed as Death, and who explains that we sometimes deal with our real fears in life by dressing up as fears that we can handle.
Bobby finds himself in a football-kicking slump after he promises to make a field goal for Oscar during a Monday Night Football game. When a pep talk from Porter isn't enough to get Bobby out of his losing streak, he must discover a way to get his focus back on the game before he is cut from the team. It's Nina to the rescue with a little prompting from Porter behind the scenes. ABC's NFL Monday Night Football commentators Al Michaels, Dan Dierdorf and Boomer Esiason guest star as themselves.
Bobby is shocked when he fails his mandatory drug test, which leaves Oscar doubting the integrity of his football-playing uncle. The strictly drug-free Bobby is determined to clear his good name with the help of Porter and Dena, but their solution only leads Oscar to further question Bobby's morals especially when lawyer Dena gives Bobby the means to cheat on his second and final drug test. Ultimately it turns out that Bobby had been eating Rose's pet bird's bird seed, which contains poppy seeds and therefore led to a false positive result for Bobby. A difficult moral dilemma is it right to cheat in the name of what you know to be true is treated seriously and without condescension in an exceptionally well-written episode.
Frustrated when Porter rejects Bobby's addition of a sexy poster to the kitchen decor, refuses to allow him to throw a birthday party for Oscar, and rejects the outsized gifts Bobby brings home for his nephew (a huge dog, a monster television system), Bobby demands a larger share in making decisions and begins by deciding to buy a new, much bigger house. Challenged by Bobby's assertion that he has always been afraid of change, a stunned Porter agrees to the move, then has second thoughts when he realizes how much of his life is tied up in the house he and his late wife made together. Compromise finds Oscar enjoying a lavish party, complete with pony, while Bobby brings home a huge boat he has purchased and Porter finally keeps his promise to phone the attractive nurse he met in episode 1.
When Bobby mocks Porter for putting encouraging notes in Oscar's school lunches just as their mother did to him, Porter realizes that his parents treated their sons very differently and had very different expectations of them. Meanwhile, pushed beyond the limit by Bobby's childish teasing, Dena quits and is replaced by a driver whose total absence of humor makes Bobby realize just what he's done.
Porter becomes depressed after he gives a talk on Abraham Lincoln to Oscar's class and literally bores the students to sleep: teaching is his only skill, but perhaps he's not as good at it as he has always assumed. When Bobby discovers that Porter has the same effect on his college students, he tries to convince his brother to liven up his act by convincing him that ""smart and interesting are two different things."" Meanwhile, Dena is outraged when Porter's new teaching assistant just happens to be a gorgeous blonde and accuses him on carrying on a tradition of academic sexism -- then turns up as a blonde herself. Bobby concludes that she is secretly sweet on Porter. Will time prove him right?
After he scares off his blind date Gretchen with neurotic pre-date jitters, Porter despairs of ever going out again -- until Bobby, Oscar and Rose try to convince him to ask Rose's mother Marilyn out. At first incredulous, the pair decide to give it a try, but Porter offends Marilyn by coming on like ""a pompous jerk"" about the difference in their backgrounds. A second attempt goes better until Rose warns Porter that he had better not disappear like all the other men in Marilyn's life have, and Porter becomes obsessed with the idea that he will destroy his friendship with Marilyn and Rose's with Oscar. Meanwhile, Dena misinterprets Porter's remarks about falling for someone ""who comes to my house every day.""
Porter is very proud of his trophy date, gorgeous model Amy, who has a thing for sensitive intellectuals. Trouble is, she fancies herself a brain herself, even though her head is obviously mostly air; and Porter has a tough time convincing himself that he interest in her is based on shared ideas rather than physical interests. Then Amy flabbergasts him by enrolling in one of his classes, making it impossible for ethical Porter to date her, and torture for him when she drops in for extra tuition she badly needs. Meanwhile, jealous Bobby bets Porter he can make any woman fall for him -- even Dena.
The brothers' mother sends them a box of stuff from their childhood, reviving ancient rivalries over their collection of miniature sports cars (which a trip to a collectors' store reveals to be quite valuable). The box also contains a sweater which belonged to Laura, Porter's first girlfriend, and he decides to contact her to return it -- leaving Bobby to agonize over the fact that Porter never knew Bobby slept with Laura, and his fear that discovering the truth with devastate Porter.
Attempting to play ball with an appalled Oscar and Rose, Porter accidentally throws Bobby's football under a garbage truck, fails to understand Bobby's rage at the destruction of his ""lucky"" football, and throws his brother out of the house. When Bobby simply moves in unilaterally with Dena, she must scheme to reconcile the warring brothers by convincing each of them that the other secretly hero-worships him. Meanwhile, Dena takes refuge from the unbearable Bobby on Porter's couch, then persuades Oscar to sleep downstairs in Bobby's room while she takes over Oscar's bed -- and Porter, thinking she is Oscar in the dark, gives her an affectionate kiss.
When Porter discovers that Bobby is dating Oscar's teacher Ginny, he orders him to put a stop to the relationship after a humiliated Oscar uncovers the fact that she has spent the night at the house. But when Porter inadvertently asks Ginny out on a date, the siblings begin to childishly fight over her, so they leave it up to Ginny to choose which brother she would most like to go out with.
After impulsively setting out on the road in an RV with Deena as passenger, Porter and Bobby find themselves broken down at a garage owned by a strangely familiar odd couple of feuding brothers-in-law whose relationship strangely reflects on their own.
Porter and Bobby find themselves in an emotional predicament when Bobby is unable to say ""I love you"" to Oscar, and Porter finds it difficult to utter the same words to Bobby. In an attempt to discover the root of their problem, Porter calls upon their free-spirited mother for some family advice -- but her off-the-wall revelations only make matters more complicated.
When Bobby tries his hand at being a shock jock while hosting a sports radio talk show, he ends up insulting his listeners and prodding an irate caller to meet him at home to settle a score -- inadvertently giving out Porter's address over the air. But it's a terrified Porter and Oscar who need protection when Bobby hires a burly bodyguard who takes his job of guarding the loose-lipped football star a little too seriously.
After realizing that he has no friends, Porter tries unsuccessfully to become pals with a group of construction workers who are fixing his home. When Bobby teaches his clueless brother how to be less of a snob and more of a man's man, Porter befriends one of the macho workers and takes him to a basketball game -- with disastrous results.
When Porter and Bobby are both scheduled to appear on ""Politically Incorrect With Bill Maher"" on the same show, Bobby humiliates Porter by stealing his notes in order to make himself look smart. But Bobby finds himself in a desperate search for intelligence when he's invited back to the show, which includes political legend Dr. Henry Kissinger on the panel, and will do anything it takes to not make himself look like a fool.
While a jealous Bobby pouts over the attention Dena is giving to her new client, Gino, a race car driver, Porter humors Oscar by letting him punish his father for a high school prank that happened years ago. Meanwhile, when Porter passes on an invitation from Dena to attend a benefit with her because he's been ""grounded"" by Oscar, the scorned sports agent storms out of the house. But when Porter changes his mind and decides to go after Dena, he crashes the party and is heartbroken when he finds her in the arms of another man.
Porter's scheme to win Dena's heart by trying to outwit Gino, her race car-driving boyfriend, in a battle of intellectual conversation begins to backfire on the lovesick professor. Meanwhile, when a small earthquake shakes up the usually unflappable Bobby, he demands to be traded to another football team in order to get away from the San Francisco tremors. But when the team owner and fans think that Bobby is just making a play for more money, public sentiment begins to turn against him. Just as Deena admits to reciprocating Porter's feelings, Bobby learns he has been cut from the team.