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.

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

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 guys deal with a new rival for their business, a beautiful buxom woman who opens a dance club down the street from the Fifty-Fifty Club, by holding a bogus contest to attract new customers. The trouble comes when the guys decide to fight fire with fire, and rig a bogus contest of their own, but with disastrous results.

Deciding they need a company car, Malcolm buys a lemon, which Eddie quickly replaces with a fully-loaded, high-priced SUV. Their drastically opposing views about spending money threaten to divide the two best friends until they agree to try a little role reversal to better understand how the other one thinks. Meanwhile, Nicolette, Leonard and Doug are on their best behavior, hoping to win ""Employee of the Week"" and the bonus that comes with it.

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.

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.

Malcolm and Eddie are thrilled when the Kansas City Chief's star running back visits the Fifty/Fifty Club and gives them free tickets to his next game. But after Eddie accidentally gives the famed football player a concussion that costs the Chiefs the game, Malcolm and Eddie become Public Enemies number one and two.

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.

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.

After Leonard's date publicly humiliates him at the Fifty/Fifty Club, Malcolm and Nicolette try to cheer him up by sharing their ""worst date"" stories. But nothing can top Eddie's date that night when he's lured by a woman named ""Sinful Sally"" to her apartment, unaware that she plans to broadcast their rendezvous live over the Internet.

Eddie agrees to buy Malcolm's lottery ticket and has to face the consequences—again and again and again—when the numbers hit.

With Malcolm sound asleep, robbers break into the apartment and steal all the furniture and strip the house of all its contents. They hire an interior designer to redo the apartment, but find out she not only has an eye for style, but a taste for a con game.

Eager to make her club Kansas City's most popular night spot, Malcolm and Eddie's chief rival, Mia, makes Eddie an incredible offer he may not be able to refuse. Meanwhile, Nicolette enters a short story contest, transporting the gang back in time to the 1920s when two rival nightclub owners resorted to far more villainous tactics to be number one.

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.

Malcolm and Eddie try to outdo the rave review for Mia's nightclub by convincing her DJ boyfriend to do a live broadcast from the Fifty-Fifty Club. But when she sees how successful the broadcast is, Mia resorts to an outrageous lie about Malcolm to turn things back in her favor.

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.

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.

For Malcolm's thirtieth birthday, Eddie surprises him with a chance to watch an upcoming baseball game from the sportscaster's booth. But the biggest surprise comes when Eddie creates a clever diversion allowing Malcolm to fulfill his lifelong career fantasy and serve as commentator for the game, with disastrous results.

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.

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.