After Ashley's single becomes a hit, Will decides to become her manager, although things soon go awry when they both realize that fame is not all it's cracked up to be.
Examples:
- Acquired Situational Narcissism: As the success of her single goes to her head, Ashley becomes snobby, demanding and overall insufferable towards Will, Carlton and Hilary.
- Comically Missing the Point: When Ashley stops Carlton from audibly eavesdropping on an argument between Uncle Phil and Will where the latter is fired as her manager, his outlandish body language shows that he wasn't happy with the news. Yet, an annoyed Carlton bemoans that they'll never know how he took it in spite of still being able to witness his reaction.
- Group Hug: Ultimately when Will and Ashley hug and make up over her failed career, Carlton spots them and runs up while shouting "Oh, you guys!" as they also embrace him.
- Ironic Echo: After Will is ousted from managing Ashley and Uncle Phil tries to convince him to come back home, he keeps saying things like "Home? Oh, I have no home!" When he ends up being kicked out of his high-priced apartment and asks to come home, Uncle Phil then turns it around and states "Home? I thought you had no home".
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One-Hit Wonder: Sadly, Ashley's song ends up being this due to it being overexposed, and no one being interested in it anymore. - Shout-Out:
- After Ashley becomes a snobby pain, Geoffrey suggests that they throw some water on her and watch her melt.
- When Gordy Berry introduces two young, dreadlocked associates of his to Will, he identifies them as Rob and Fab.
- When Will is imitating listeners to request "Make Up Your Mind", one of them is a vaguely Latino/Hispanic man named Tony.
