Sandy Wexler (Adam Sandler) is a talent manager working in Los Angeles in the 1990s, diligently representing a group of eccentric clients on the fringes of show business. His single minded devotion is put to the test when he falls in love with his newest client, Courtney Clarke, a tremendously talented singer who he discovers at an amusement park. Over the course of a decade, the two of them play out a star-crossed love story.

Jess - a bubbly offbeat teacher who is known to burst into spontaneous song - catches her boyfriend with another woman, and needs a new place to live. She moves into a loft with three single guys she's never met before. Nick is a jaded law-school dropout, who usually just wants to be left alone. Schmidt is an flashy businessman, who believes he is a gift to women. Winston is a former athlete who doesn't know what to do, but really needs to win whatever it is. Can this dysfunctional group handle the "adorkable" new girl?