The Drew Carey Show

S07:E19 - Bringing Up Boss

When Winfred-Louder's new owner, Lord Mercer (recurring guest star JIM PIDDOCK), appoints his flighty 19-year-old daughter, Milan (recurring guest star JESSICA CAUFFIEL - "Legally Blonde"), as the store's president, Drew asks Kate to teach Milan how to be a businesswoman--with disastrous results. After listening to Kate's advice and concentrating on work instead of her boyfriend, Milan is so frustrated that she terminates staff members and demotes Drew to the loading dock. Finally, Milan realizes that she needs Drew to work in his former position again, but when she finds out that her boyfriend had sex with Kate, she becomes suicidal.