While at Six Flags, Sandy sees a young woman, Courtney Clarke, performing in a open show in a park for kids. Immediately entranced by both her voice and her beauty, he convinces her that he can make her a star once he meets her dad, an Alaskan prison guard. The manager explains that he always has to keep a professional distance with his clients, citing his first client as his cautionary tale, saying Alfred had been his best friend but was soon dumped by him and later became huge.
Sandy gets Courtney into a studio to record her first single, which becomes a hit through Capitol Records. They record several singles that become hits, but his antics continue to cause her trouble. Believing she has a stalker, Courtney calls him over. Poking outside her home, he discovers it was only a racoon.
When she invites him in to clean up, Sandy discovers that rapper Bling is her boyfriend. Bling has got her a publicist and convinces Sandy that his presence is a problem to Courtney's potential fame, so he resigns as her manager.
Miserable, Sandy cries for hours. Not able to escape reminders of Courtney, which are everywhere as she becomes a star, he goes to his neighbor Cindy's. She's been throwing herself at him for ages, but when the moment comes he can't, as her bed-ridden stroke-stricken husband is watching.
While Sandy continues to struggle with both his feelings for Courtney and his clients, she grows more and more famous, eventually winning a Grammy. Bobby soon sees success when Sandy helps him become champ, while Courtney, feeling unsatisfied with her fame, spirals into drinking and a string of failed relationships.
Contacting Sandy as she's wasted, Courtney seeks comfort with him, but he is a gentleman and doesn't take advantage of her. The next day, they pal around together at a driving range then, in the evening, they watch his wrestler client Bobby win a championship match.
That night, sitting by the pool, Courtney marvels at how selfless Sandy is, always putting others first. Trying to get him to admit his feelings, she half gives up and they have a one night stand before she flies to NYC to do a video with Lenny Kravitz.
Depressed by Courtney's decision, Sandy is more distracted than ever, which costs him all his clients except Ted. He accompanies him with negotiations at a TV network to take over a program whose clown host just committed suicide. As soon as a deal is reached, Sandy is rushed to the hospital for a mild heart attack.
Sandy wakes in a luxurious hospital room, thanks to Courtney. She tells him that she's quitting the business and leaving to get married in Seattle with an entrepreneur.
While back at Six Flags, he meets Alfred, finally revealed to be Weird Al Yankovic. Al convinces Sandy to stop telling people what he thinks they want to hear and, instead, tell them the truth. To this end, Sandy enlists many of his contacts, calling in favors.
Sandy has his landlord bring Courtney to Griffith Observatory, where he admits his feelings to her, which she reciprocates, and they're married in a ceremony officiated by one of Ted's puppets (The Aurora Boreal is in the Roof). Sandy's newfound honesty also gets him back his clients as well as many new ones. After twenty years, Courtney and Sandy are married for real.
