7. Bridget Hennessy (Kaley Cuoco) as Britney Spears in 8 Simple Rules
Air Date: 10/29/04
As the stereotypical sitcom Hot Daughter, Bridget regularly attempted to leave the house dressed in the skimpiest clothing possible. No surprise then, that on Halloween she attended her own Student Body President-hosted party as Britney Spears, complete with pigtails and "Hit Me Baby One More Time" plaid skirt.