Malcolm inadvertently places a large bet on Eddie when he competes in a NASCAR race. Nicollette fears a dream she had about Eddie might come true.

Malcolm uses tough love on his sister who gets fired and dumped in the same week.

It comes as a shock to Malcolm and Eddie when they learn that their old pal, Nelson Carter, is getting married. After all, there was a better chance for the Pope to get married before Nelson ever decided to settle down. But on the day of Nelson's wedding—and after a wild night at his bachelor party—the two begin considering settling down themselves.

Malcolm suggests Eddie settle his differences with an ex-con in the boxing ring.

Malcolm's estranged brother comes to town, igniting old tensions, but reviving old family ties. Meanwhile, Nicolette takes a job in a bowling alley, and tries to get along with unruly customers.

Nicolette stays with Malcolm & Eddie while her place is being painted and her quirks & habits drive the guys crazy.

Malcolm and Eddie receive tickets and all expense paid trip to New York to appear on a panel for a sports fanatic show, on the Jerry Stein show. So the guys show up for the taping dressed in weird sports-fan attire, but are unaware that they are actually on a talk show about devil worshipers. They can't understand why the audience is jeering and booing them, until the rest of the panelists come out on the stage.

A contractor (Coolio) consults Malcolm and Eddie about building a club in Chicago.

As the profits from the 50/50 club begin to grow larger and larger, Malcolm and Eddie clash over whose money-making strategy is best. Malcolm believes in investing his money in the stock market, while Eddie believes in betting on horse races.

Ashley catches Malcolm kissing Olivia. After their breakup, Malcolm goes into a funk and Eddie goes to extraordinary lengths (and heights) to pull him out of it. Eddie tries taking Malcolm on a hot-air balloon ride.

Dexter returns and asks Eddie for another loan—it seems he's been evicted from his apartment yet again. Heeding Malcolm's advice, Eddie doesn't give him the loan but takes a stand to help Dexter back on his feet. However, the situation changes once Dexter gets coffee spilled on his lap at the club.

Hoping to duplicate the incredible success of the movie ""The Blair Witch Project,"" Malcolm recruits Nicolette, Leonard, Doug and a very reluctant Eddie to help him make a similar film about a local Kansas City legend, the Tapawingo Witch. But after they head deep into the woods to film the documentary, a series of frightening events spook the novice filmmakers, blurring the line between fantasy and reality.

Malcolm, Eddie, Nicolette, Leonard and Doug head to North Carolina to spend the holiday with Malcolm's Uncle Buddy. But panic sets in when they reach his uncle's empty house and discover the town has been evacuated because of an oncoming hurricane, and now they're caught right in the middle of it.

When Eddie's cousin Dexter decides to get married, he asks Eddie to be his best man and Malcolm to be his ""man of honor."" But Dexter's promise to his fiancée that they'll be no strippers at the bachelor party is broken when an unaware Malcolm hires a sexy stripper, and then has to bring the two lovebirds back together when the wedding is called off.

When Hawkins dies suddenly of a heart attack, his daughter Ashley is surprised to learn that she can only inherit his 10 million dollars is on one condition—that she marry Eddie within 30 days. But Eddie soon discovers that saying ""I do"" to wealth and marriage may devastate Malcolm, who has taken drastic measures to try and forget about the feelings he still has for Ashley.

When Malcolm's Uncle Buddy dies, Malcolm is entrusted with his ashes to scatter in the Missouri River. But when Eddie mistakenly uses the urn for a vase, Uncle Buddy winds up in a very different place than expected, and Eddie has to go to outrageous extremes to keep Malcolm from finding out about the final resting place of his dearly departed uncle.

A newly-confident Dexter visits the guys with his pregnant wife in tow, only for her to go into labor just as a long streak of bad luck events take place in their lives.