Tom Farrell, an A&R representative for a major New York record label, is having a very bad day. He is fired from his job and dumped by his girlfriend. However, Tom is not deterred. Determined to start his own record label, Tom finds a prodigy singer, Wayne, but soon finds that sticking with your convictions isn't easy. Meanwhile, Tom meets Julia, also an A&R rep who loves good music just as much as he does.
Tom is settling into his new job at True Vinyl Records just as their benefit concert begins to fall apart. Using his contacts from his old job, he enlists Zoe, America's top pop star, who now chooses this exact time to change her image.
Meanwhile, Mike must deal with Karen's choice of nanny -- a very attractive woman. Also, Shooter begins dating a woman whose candor and honesty is at first refreshing, but then backfires.
It's music video time for Wayne. At work Tom runs into a slight problem getting the gang on-board the music video concept because their record label doesn't have the money for a quality video. He convinces them to spend the money, after mentioning his connection to an MTV bigwig. After taking a day to interview potential directors, Tom is informed that the process is costing too much money. Julia suggests that they use an independent film director who had just done very well at Sundance. They hire him with the understanding that money will be tight. Conflict ensues.
Meanwhile, the married couple, Mike and Karen, are baby sitting a young puppy. Is Karen testing Mike’s parenting skills? Also meanwhile, Bran tries to get her boyfriend accepted by the group. She is worried that they won’t like him, forcing her from the group. And Jake is trying to make it to the big-time and thinks that he needs a catch phrase, so he comes up with one. Unfortunately . . .
Tom’s old girlfriend returns, and Tom must help get her band an appearance on the David Letterman show. Trouble develops, though, when the ex-lovers start to get feelings for each other again.
Tom attempts to promote the newest album by the Barbarian Brothers. Problems arise, though, when the female critic he tries to get a good review from notes that she has feelings for Tom. Meanwhile, Tom’s friend Bran has relationship problems of her own.
Tom discovers a great new artist, Ray Grimaldi, while attending the funeral of Carmine Grimaldi. Ray's father, Carmine, was the owner of Tom's favorite pizza parlor and must now try to support the family. Tom prefers that Ray be given the chance to develop his singing talents, while the family prefers to have some food to eat.
Meanwhile, Tom's friends Shooter and Mike are mugged.
Tom searches for singer Gordon Decker so that True Vinyl can complete and release Decker's second music album. Decker went missing years earlier due to the pressure of attempting to complete that second album.
Phil tries to lure Wayne to Goliath Records and offers Tom his own independent label if he will come back to Goliath and bring Wayne with him; Jake breaks up with Clete after discovering him with another man; Shooter is given a promotion by his father, who wants him to go to Chicago for eight weeks to oversee a project; Karen goes into labor but complications arise at the hospital.