Barry, Ben, Bobby, and Jason are best friends with the nickname, ""Four Kings of New York."" When Ben's mother passes away, she passes her swanky apartment onto Ben, who immediatley invites his best friends to move in with him.

The friends use Ben's article assignment about one night stands as an excuse to party all night at an exclusive place. Meanwhile, Barry baby-sits his ex-girlfriend's two kids - twins, and Bobby and Jason try to give each other tips on picking up women, leaving Ben at the bar to learn from his own train-wreck caliber mistakes.

Ben decides to set Barry up on a blind date with a co-worker of his. However, Barry becomes suspicious because Ben didn't ask the girl out himself and is convinced something must be wrong with her. Bobby and Jason, meanwhile, get enrolled in a game of chest. The game climaxes when Jason meets with his boss over a possible promotion.

Barry gets a date with a girl Ben had a crush on in high school. To show his affection, Ben videotaped a poem he wrote back in high school but didn't actually show the tape to her until now. Barry immediately gets jealous once he finds how well his date and Ben get along and decides to make a tape of his own. Meanwhile, because of his insecurity, Jason's boss demotes Jason after he discovers an ""endowment"" Jason possesses. Bobby comes to Jason's aid and tries to reason with his boss.

Ben is chosen to work on a campaign for a Democratic candidate and attends a campaign function with Bobby. Meanwhile, Barry finds Jason eating dinner with a man and is convinced that he is gay. After getting confronted with this, Jason denies being gay but admits that he is something else - a Republican. Ben then questions the friends' relationship after finding their beliefs differ.

Jason is excited when his boss gives him the job of redeveloping a low-income housing building into luxury condos. Ben decides to write an article on the former tenants who were evicted from their homes, which creates problems between the two. Meanwhile, Bobby and Barry are getting paid for befriending two elderly woman, but Barry soon finds out his woman wants to be more than just friends.

Jason is stuck watching an iguana when the owner tricks him into holding it and leaves. Ben's new girlfriend does not take criticism very well.

Ben is setting new house rules for the apartment. There might be more to his obsessive behaviour than catches the eye.

Bobby's catchy tune is heard by Barry's boss, who gives Bobby the opportunity to record it while Barry gets the opportunity to produce it. Jason and Ben find a cell phone on the floor of a taxi. After looking through her phone, they come to the conclusion that she is hot and begin fighting over who gets to ask her out.

A few high school kids want the table at the coffee house where Barry, Ben, Bobby and Jason usually sit. They don't want to leave the table to the kids but they are all afraid to get into a fight.

After Barry gets a peek at Jason's much-larger paycheck, he decides to pick up the check at an expensive French restaurant, spending more on his boss's credit card than he can possibly pay back.

Ben thinks he has made a romantic connection with a neighbor he met in the lobby.

Lauren is getting divorced. Ben tries to be just friends with her, since he has the bad habit of falling for the "troubled girl".