The Drew Carey Show (1995)

S03E09 Drew's Brother

Drew's older sibling, Steve, unexpectedly shows up, struggling after a recent breakup and job loss. Kate persuades Drew to hire Steve in the cosmetics section. One day at work, Drew is shocked to see his brother in a full women's outfit, including a wig; Steve confesses that he is a cross-dresser. This revelation prompts Mr. Wick to insist that Drew terminate Steve's employment without delay.