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