A wealthy tycoon challenges Eddie to a high-stakes game of golf.

Holly passes Malcolm off as her boyfriend when her parents come for a visit. But all goes awry when Malcolm is caught in a compromising situation. Eddie seems oddly attracted to a psycho chick. And Tim meets Danielle for the first time, and its love at first sight.

A rival towing company owner, runs Eddie out of business, and gets him to work for him. But Eddie decides to turn-the-tables on his unscrupulous boss, and get his business back.

After finding out that the success of the Fifty/Fifty Club has driven its competing club, Club Misdemeanor, out of business, an accident damages the club forcing Malcolm and Eddie to try and find financing to reopen the club. To make matters worse, Mia, former owner of Club Misdemeanor becomes their new landlord. So in order to keep the club from being closed down, the guys decide to take on a third partner.

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.

Things are going so well for Malcolm and Eddie with their new girlfriends that Malcolm invites Helena to move in with him, and Eddie tries to double his fun by moving in with the twins that he's dating. But the romance quickly fades when Malcolm realizes what a slob Helena is, and the twins drive Eddie nuts fighting for his attention.

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.

The duo agrees to listen to a realty sales pitch in order to get a free seven-day cruise.

While vacationing in Las Vegas with Malcolm and his new girlfriend, Eddie can't resist the lure of the crap table. But when his lucky streak turns unlucky to the tune of $50,000, he has no way to pay his debt, until a wealthy female offers to cover his losses on one condition—that she gets to sleep with Malcolm in return.

Aspiring sportscaster Malcom finally gets a chance to be on the air at the radio station but instead of calling the plays, he's given a dee-jay's graveyard shift. Surprisingly, Eddie ends up as the only one who can get his exhausted roommate through the long nights.

As Malcolm prepares for Halloween, fearful Eddie tells a story of a devastating family curse.

A man trying to bring a fake lawsuit against the bar, inadvertently dies, just as the guys get a visit from the city's toughest health inspector.

The guys land in jail when they try to scalp Jodeci concert tickets.

Tim is forlorn over his breakup with Danielle. He writes her a love letter to express his deepest feelings for her, but hands it to Malcolm to pass to her. But when Tim's love letter falls into the wrong hands, everyone who reads it becomes entangled in romantic misunderstandings, thinking that the letter was intended for them.

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.

An unlikely romance blossoms between the guys and their girls, during an employee camping retreat in the woods. After being stranded in the woods overnight, Nicolette finally gets Eddie to surrender to her ample womanly charms. Meanwhile, Holly shares bodily warmth with Malcolm, and learns a new respect for him.

Eddie annoys Malcolm when he deviates from their established system of picking their joint weekly lottery ticket numbers and instead chooses what Malcolm considers a dumb mix - 5, 10, 15, 20, 25 and 30. Malcolm forgives Eddie's indiscretion when all six numbers come up, making them instant millionaires... or so they think.... Unfortunately for the mismatched roommates, for the first time in Missouri state history, there's more than one winner of the Instant Millionaire game - many more. When the money is divvied up, Malcolm and Eddie are able to redecorate their apartment just in time to impress Bridget, a young attorney and her roommate Nicollette, a parking enforcement officer, who move in across the hall. Strongly attracted to Bridget, Malcolm is summarily spurned when she makes it clear she's dating NBA Rookie of the Year Damon Stoudamire. Realizing he's at a crossroads in life, Malcolm decides to buy the bar from Kelly. Eddie uses his half of the money to convert the tow truck gar

The club puts on a 70's promotion and everybody dresses up in 70's attire, and grooves to the funk. Eddie gets into the spirit of the 70's, so much so that he remains there even after the promotion is over. When Nicolette arranges for him to get a city contract fixing parking scooters, Eddie's priorities become confused, & business & friendships begins to suffer. Eddie finally admits he's a Funk-aholic.

Simone tries to win Malcolm's heart through his stomach with some special chocolate cookies, but once Malcolm tastes them, he only wants to use them to go into the cookie business with. Meanwhile, McGinley tries to lure Simone away from Malcolm, to work in his bar.

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

Malcolm tries to settle his grandparents' quarrel after Malcolm's grandfather gets kicked out of the house and moves in with Malcolm & Eddie. Nicolette gets a new roommate named Regina, who has eyes for Eddie, but Nicolette remains determined continue persuing him.

Malcolm acts as chef Simone's husband to fool her high-school nemesis.

Eddie and Malcolm try to return an expensive leather sofa Eddie bought with rent money, even after he accidentally painted graffitti on it.

When Eddie's beloved tow truck Broncula breaks down, he must raise money to repair ""her,"" so he secures a wild array of odd jobs which quickly wear away at Malcolm's quality of life.

Nicolette's desire for a meaningful relationship inspires her to try celibacy, and inspires the others to a challenge to see who can abstain from giving in to their sexual desires the longest. As the gang slowly gives in to the temptation one by one, everyone is surprised at who the final winner is.