Barry, Ben, Bobby, and Jason have been best friends their entire lives and haven't even spent a birthday apart. When Ben's grandmother, who has dubbed them the "Four Kings of New York," passes away, Ben inherits her large, posh apartment. Ben, of course, asks his friends to move in with him, but his girlfriend Jenny conveniently decides that it's a good time in their relationship for them to move in together. As the guys prepare to make the move, having decided that there's enough room for all of them, Jen gives Ben an ultimatum - his friends or her.
When Ben is hired to write an article about one night stands, the guys use this as an excuse to have a night out at an exclusive party. It also provides ben the opportunity to prove he's not only a "relationship-type."
Barry, on the other hand, gets stuck at home babysitting his ex-girlfriend Sharon's (guest star Kathryn Hahn) twin daughters. At the bar, Bobby and Jason run interference in each other's pursuits at picking up women while Ben, after a few flubbed attempts at using their flawed advice, is finally successful.
Ben decides to set Barry up on a blind date with his colleague, thinking that the two will have a lot in common. Barry, suspicious because Ben hasn't asked her out himself, becomes convinced that there must be something drastically wrong with her. When they finally meet, Barry proceeds to ask her a series of inappropriate questions to determine her faults, only to upset her and drive a wedge between her and Ben as well.
Meanwhile, Bobby and Jason are engaged in a heated game of "chest," which comes to a head while Jason is meeting with his boss at a fancy restaurant to discuss a possible promotion.
Barry lands a date with a girl Ben had a crush on in high school. After the girl refused to go to prom with Ben, he videotaped a poem for her to show his affection. The tape was never revealed until now when Barry brings her home to meet the guys and he grows increasingly jealous over how well Ben and his date are getting along. Barry's plan backfires and he finds himself making his own little videotape
Meanwhile, Jason is demoted in his job when his insecure boss discovers a certain "endowment" that Jason has. As any good friend would do, Bobby finds himself trying to convince his boss that there is no real reason to feel threatened by Jason.
Ben is excited to be working on the campaign of the local Democratic candidate and asks Bobby to accompany him to a campaign function. When Barry spots Jason at a restaurant dining out with another man, the guys jump to the conclusion that Jason is gay. They confront him and Jason adamantly denies it, but admits he is hiding something from them -- that he's a Republican. Ben is outraged to discover that Jason is working on the campaign of the opposing candidate and questions how they can be such good friends with such drastically differing beliefs.
Jason gets a huge job opportunity when his boss puts him in charge of converting a low-income housing building into luxury condos. Ben decides to pitch the redevelopment story to New York Magazine in a fit of desperation at his dead-end writing career. His assignment to write an expos? on the tenants' forced eviction leads to a large rift between the friends.
Meanwhile, Bobby befriends an elderly woman in their apartment building who begins paying him for his friendship. When he recruits Barry to do the same for one of her friends, Barry realizes that his date expects more than companionship to get her money's worth.
A frequent customer at the local coffee shop (known as the "Iguana Guy" because he walks around with an iguana on his shoulder) tricks Jason into holding the reptile and then abandons him. As Jason attempts to pawn the animal off, Ben is becoming better acquainted with Angela, an aspiring writer he just began dating. Ben soon discovers that Angela doesn't take criticism of her writing well and pays the price for his editing.
When Bobby's catchy tune "Angel from Heaven," makes its way to Barry's boss, who is a big producer, Bobby is given the chance to record his music and Barry is given the chance to realize his career ambition to be a music producer.
Meanwhile, Jason and Ben find a young woman's cell phone on the floor of a taxi. As Jason and Ben invade the woman's privacy and rummage through her cell phone for information, they determine that she is their hot dream girl and begin fighting over who deserves to ask her out.
Ben is convinced that he had a "moment" with his beautiful neighbor Lauren after running into her in the apartment lobby. The only problem is that Lauren is in a complicated and not to mention miserable marriage. Unable to shake the thought of her, Ben cannot resist trying to comfort Lauren, while she is content with taking all her frustrations out on him. Meanwhile, Bobby moves in a fifth roommate, which the guys' are opposed to at first, but it doesn't take long for them to warm up to the idea.