#39: Miley Cyrus as Missi
Miley Cyrus guest-starred as Missi, Jake’s whirlwind of a girlfriend. Fast-talking, energetic, and hilariously overwhelming, she brought a burst of chaotic fun to the Harper household. Missi’s over-the-top personality clashed perfectly with Jake’s laid-back cluelessness, making her one of the show’s most memorable late-series guest characters.

When she appeared in 2012, Cyrus was in the middle of her transition from Disney Channel star (Hannah Montana) to more mature roles. Her cameo on Two and a Half Men was a clever way to showcase her comedic timing and appeal to an older sitcom audience.
