Pennywise or Penny Wise may refer to:
- Pennywise (character), also known as It, and Pennywise the Dancing Clown, the title character in the Stephen King novel It and its film and television adaptations
- Pennywise (album), a 1991 eponymous album by the band
- Pennywise (band), an American punk rock band
- Penny Wise, pseudonym of Jon Vitti (born 1960), American screenwriter