Jim is an abrasive but lovable suburban father. Much like his real life counterpart, Jim's character is noted as a fan of Blues music, as well as the Chicago Blackhawks, Chicago Bulls, Chicago Bears, and the Chicago Cubs. He's married to a gorgeous woman, Cheryl, and raises his five children – Ruby, Gracie, Kyle, and twins, Gordan and Jonathan – in a big house. Everything is perfect for Jim, if it wasn't for the messy situations he gets himself into and his laziness, which often makes him search for alternative ways of doing things with less effort. Of course, having his wife's siblings hanging out at his house all the time is no help. While Andy might be one of his best friends, Dana often teams up with Cheryl against Jim.
When Jim finds out that Cheryl has been paying 7 dollars to have the groceries delivered to their house, he insists that he does the shopping himself in order to save that incredible amount of money. Once at the supermarket, he sees how married men are "domesticated" by their wives and decides to rebel against Cheryl by shopping everything but the items on the list. Cheryl decides to turn the table on Jim and he does the same, until they end up going to a formal party on robes and underwear with their bodies all painted with lipstick. Cheryl finally gives in and they settle on paying the delivery boy the seven dollars in order to spare the Spice Channel subscription.
Jim is horrified when he sees his son Kyle with a green Packers ball. He tries by all means to change it for a Bears one, but the kid just can't let go of the green ball. Jim has nightmares about it and takes Kyle to his work in another attempt to get rid of the Packers ball. When he realizes there's nothing he can do about it, he does a little alteration on the ball so they can go to the Bears game peacefully.
Jim wrestles with his conscience after he cheats at a church fundraiser bingo game.
Cheryl says a friend of hers got jewelry for his wife for no reason and Jim says he's probably cheating on her. After Cheryl takes it offensively that Jim won't buy her jewelry because he doesn't think he has to – after all, they are married and he isn't cheating – he goes out to shop for earrings, only to find out he knows nothing about Cheryl. After spending three days dedicating himself entirely to paying attention to Cheryl – with a bit of Andy's help – Jim finds out that Cheryl's friend was indeed cheating and they finally make up.
Jim and Cheryl encourage the girls to make a lemonade stand and raise money for their scooters. What was supposed to be a lesson about the value of the dollar turns into a racy competition among neighbors when Bill and his next door neighbor Driscoll set up little amusement parks in their years. Dana and Andy pitch in, while Cheryl tries to stay out of it – until she gets into a catfight with the neighbor's wife. Once the police is called in, Jim realizes he's lost the purpose of the lemonade stand and decides to give the girls the rest of the money for the scooters.
Trying to lighten Ruby's homework load – and therefore look like he's helping her – Jim tells Ruby's teacher that Cheryl can't read.
It's Halloween and Cheryl is trying to host "the" party so she can own Halloween in the neighborhood. Dana brings in her newest date, Hank, who carries an awful lot of similarities to Jim. While refusing to admit she's dating Jim, Dana realizes the truth when she accidentally pinches Jim's butt thinking it was Hank. The next day she and Cheryl have a fight over the whole situation, which leaves it up to Jim and Andy to fix the friendship between the two sisters.
Gracie and Ruby have nightmares after Jim secretly takes them to see a scary movie. (ABC)
Jim creates an imaginary friend to avoid going to a couple's baby shower with Cheryl.
Cheryl cajoles Jim into attending a couples cooking class, which turns into a disaster, so she lets Jim pick out the next couples activity – paintball.
Cheryl starts to feel taken for granted as she prepares Thanksgiving dinner. She suffers the ultimate insult when she gets stuck on the roof after retrieving her tablecloth that Jim had fashioned into a ghost for Halloween, and no one notices her absence until she unhooks the satellite. To apologize, Jim tells her that he, Dana and Andy will prepare the dinner. Jim never thinks that Cheryl, being the control freak that she is, would allow that to happen, so he doesn't make dinner. Unfortunately, neither does Cheryl.
Cheryl caters to Jim's every whim to make amends for a big fight they had the night before-except Jim doesn't remember the fight at all.
Dana admits to Cheryl that she can't afford to buy Jim a Christmas present, so Cheryl lets Dana put her name on one of the presents she bought for him. Dana innocently picks out Cheryl's big present to Jim, but when Jim is thrilled with the gift, Dana is ready to take all the credit for it.
The Devlins place a bid on the house across the street from Jim and Cheryl, to their dismay.
Dana and Jim both covet their reverend - she for romance, he for the pastor's prowess at bowling.
Cheryl forbids Jim from throwing his cop friend Danny a bachelor party with beer and strippers. She fears that Danny will show up at his own wedding with a hangover – as Jim did at their wedding. Jim and his buddies decide to take Danny for a swim in bitter-cold Lake Michigan – forcing a hospital visit for Danny. The wedding morning, Danny stays in bed, moaning and groaning, and Cheryl frets, but the doctor assures everyone there's nothing wrong with him. Jim realizes Danny just has cold feet, so he tries to convince him to go through with his wedding to Laraine, a fellow cop.
Cheryl tries to impress her boastful cousin Mindy by posing as the lead singer of Jim's band – even though she has a terrible voice. Jim agrees to perform at Mindy's engagement party with Cheryl playing the part in order to teach his wife a lesson about embellishment by making a fool of herself. However, when Mindy tells Jim that her fiancé, Eric, is a record producer, he must decide between telling Cheryl the truth and making a bad impression on Eric.
Dana's first task at the ad agency is to cast the perfect TV family for a Disney cruise commercial. Cheryl and the kids get the job, but Dana's boss replaces Jim with a handsome actor in the role of "dad."
Jim takes umbrage at being replaced as the father in a promotional shoot for a cruise line.
Gracie's recent misbehavior makes Jim think she is lying about a friend giving her a new video game.
Jim's sister, Roxanne, shows up on his doorstep, pregnant, and lets Andy believe he's the father.
Andy resents a wealthy client, but then decides to date her.
Cheryl ask Jim to use his truck to transport a giant paper-mâché grizzly bear the girls made for "spirit week" to their school – except Jim just lost his truck in an arm wrestling match and, in a gesture of macho pride, refuses to ask for it back.
Cheryl promises to take Jim's opinions seriously when she decides to remodel the bathroom, until Jim insists it include a hideous high-tech stainless steel toilet – that talks.
Pack rat Cheryl asks Jim to rent a storage unit to house seven years' worth of the kids' art projects, but Jim refuses to pay the fee, so he tosses everything out, thinking Cheryl won't notice – until she needs some of the projects for a special retirement party for Ruby's art teacher.
Thinking it might get Cheryl to let him go on a fishing trip with Andy, Jim makes a "deposit" in the "marriage bank" by agreeing to go to a couples seminar with her. Jim's plans are foiled, however, when Dr. Ted, the marriage guru, declares the whole marriage bank mentality unhealthy and Cheryl learns Jim's real motives – so that Dr. Ted must intervene.
Jim develops a friendship with Dana's new boyfriend, despite the fact that the guy dumped Cheryl years ago.
Cheryl protests when a heat wave sends the family sneaking into a vacationing neighbor's pool -- until she starts sneaking over on her own.