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.
While out for dinner and a movie, Jim loses a parking spot, and later loses Cheryl when he can't let go of it.
After Tim and Cindy Devlin's sudden divorce announcement, Andy starts spending time with Cindy, which turns into a relationship, and an urge for Cheryl and Jim to break them up.
Cheryl's 15 year-old cat Mr. Feeney dies and she wants Jim to bury it on the backyard, but Jim desperately wants to go to the Bears game. He sticks the cat in the garage freezer, planning on burying it after the game, but Cheryl finds out before he comes home. She is hurt that Jim doesn't listen to her nor care about a cat that has been longer with her than anything in her current life. Jim, feeling guilty, provides a proper funeral for Mr. Feeney and gets her a brand new dog, which she doesn't like very much at first, but starts to accept it later.
Jim and Cheryl find their romantic getaway to the Bahamas set to work out perfectly, with Dana babysitting the kids. However, at the last minute, Dana is not able to babysit. In the meantime, Andy becomes a little too obsessed with making the perfect treehouse for Grace and Ruby.
Andy is upset because no one approves or believes in his marriage to Roxanne. Jim goes to talk to her and walks in on her packing to run off with her ex boyfriend. He tries to stop her, unsuccessfully. Jim and Cheryl try to break the news to Andy before the business presentation, but he's so upset that he breaks down in tears on stage. While consoling Andy, Jim forgets about the foam hose and foam just floods the stage. Jim and Cheryl stroll in Las Vegas, glad that Andy is finally recovering from Roxanne and glad that their trip is over.
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.Watch Now:iTunes
Jim and Cheryl agree to let Ruby model for a print ad as a one-time thing, but when the photographer calls her a natural, Jim gets Ruby an agent.
Jim sets Dana up with a guy so perfect that even Cheryl falls for him.
On Jim and Cheryl's 10th Anniversary, Jim pays Dana to buy him an anniversary gift to give to Cheryl. However, Dana buys a beautiful and touching charm bracelet, going over the spending limit in the process, and Cheryl finds out that all her anniversary gifts over the past ten years were bought by Dana.
When Cheryl has a revealing photo of herself taken as a Valentine gift to Jim, he proudly shows it to all his friends.
Cheryl leaves Jim in charge of their kids and some other kids who were there to play with the girls during a Bears game. The next day, one of the kids mom calls Cheryl saying her daughter dame home repeating a swearing she heard from Jim. Cheryl apologizes for him and Jim is insulted that she always automatically takes the other person's side. Cheryl apologizes, and not too later Grace repeats the exact same word. Jim decides to teach her not to repeat it by making her say it non stop until she can't say it again. It works. 5 days later, at Ruby's ballet presentation, she slips, falls and says the word, unmasking Jim's guilt.
Andy has a new girlfriend, and Cheryl wants Jim to treat her nicely because not only is she Andy's first girlfriend sine Carrie, but also Ruby's piano teacher. During dinner, Alicia tells Jim she's a vegetarian, and not only that, but also a Peckers fan – a big insult to Jim. Alicia and Andy break up and get back together, but she keeps turning down invitations to have dinner at Jim and Cheryl's. The reason? She doesn't like being around Cheryl. Jim rubs it on her face until Cheryl confronts Alicia, who reveals it's only because she thinks Cheryl's too perfect.
Cheryl claims to like men who aren't afraid to cry, but when Jim bursts into tears after a movie, she is surprised to find herself turned off by his sensitivity.
Cheryl decides to go behind Jim's back and loan Andy $1,000 for a downpayment on a new condo.
When Cheryl reminds Jim that she beat him at racquetball years ago, he claims he was only letting her win to gain her affections, so Cheryl challenges him to a no-holds-barred re-match.
Jim and Cheryl are the perfect middle class American couple. Happily married, living in a suburban house with two adorable (but loud) little girls and a baby boy, they really can't complain much about life – except for those couple fights that neither one can ever let go, like the time Jim shut the car door on Cheryl. This time the problem is their daughter, whom Cheryl can't leave alone on her first week at kindergarten. Jim says it's because she's a woman and decides to take Ruby himself, but he also can't leave her behind. Things heat up when Cheryl discovers that not only has he been hiding it from her, but he also changed Ruby's school without talking to her. Meanwhile, Jim and Cheryl try to help Andy make up with his girlfriend.
Jim looks forward to a "guys only" weekend with Andy, but when Andy ends up dumped by Emily over a text message and when the guys stumble upon Emily's depressed ex husband, Jim decides to do his best to cheer up the guys and save what's left of their weekend.
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.Watch Now:iTunes
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."Watch Now:iTunes
Cheryl forces Jim to donate time to charity. His reluctance turns to elation when he's rewarded with a thousand-dollar check for his efforts. Cheryl insists he return the check, but Jim is itching to buy himself somthing frivolous with the money. And to really test Cheryl's integrity, he spends the money on a pricey designer handbag for her.
Jim takes advantage of a billing error on his credit card by using the windfall to treat Cheryl to an expensive romantic weekend.