The Drew Carey Show
Drew's Brother
S3 E9:
Drew's older brother Steve pays a surprise visit; he's down on his luck after going through a broken engagement and losing his job. Kate convinces Drew to give Steve a job in the cosmetics department. One afternoon at work, Drew is astounded to find his brother dressed in women's clothes, complete with a wig; Steve reveals he is a cross-dresser. Upon this discovery, Mr. Wick demands Drew fire Steve immediately.
Starring
Kate Walsh, John Carroll Lynch, Dionne Warwick