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Pennywise or Penny Wise may refer to:

  • Pennywise (band), an American punk rock band
  • Pennywise (album), a 1991 eponymous album by the band
  • Pennywise the Dancing Clown, or It, the monster in the novel It and its adaptations
  • Jon Vitti (born 1960), American screenwriter who used the pseudonym Penny Wise