Tom Farrell, a music executive, looks for love in the big apple. While looking for love he is fired from his record company so attempts to start his own. Meanwhile, Tom's girlfriend pressures him to get married to her.

Tom promises to get a famous singer he once represented to play at a benefit concert, but her lable company will not let her even though she wants to. Meanwhile, Mike and Karen look for a nanny for their child.

Tom deals with a tight budget, quirky director and looming deadline as the record company films Wayne's first video.

Tom must represent his ex-girlfriend's band and discovers that they still have feelings for each other.

Tom and the guys attend Carmine Moretti's, the owner of their favorite pizza place, funeral when Tom finds that Carmine's son Ray is an amazing singer and could be a star. But since Ray must now support his family and take over his father's business, Tom must convince Ray not to squander his talent and convince Jeff that Ray has more potential for greatness than the artist Julia wants to respresent. Meanwhile, when Shooter and Mike are mugged, they are both forced to deal with the situation in their own way.

Tom gets the chance to buy the catalogue of a singer who cracked under the pressure of the music business years ago and never completed his long-awaited sophomore album.

On the eve of Wayne's first album release, screaming teenage girls, greedy music executives and manipulative publicists are all trying to now get a piece of him. Tom is trying to protect Wayne, but Tom's old mammoth label Goliath keeps tempting him and his parents with a lucrative new contract offer and that True Vinyl is too small to take his career to the next level. Meanwhile, Karen and Mike prepare for the birth of their baby, Bran learns whether or not she got the big promotion, Shooter must finally decide if he'll take over the family business and Jake must choose if wants to face the repercussions of coming out professionally.