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Pennywise or Penny Wise may refer to:
|Look up penny wise and pound foolish in Wiktionary, the free dictionary.|
- The dancing clown form of the titular monster from Stephen King's novel It
- Pennywise (band), an American punk rock band named after said clown
- Pennywise (album), Pennywise album
- Jon Vitti, writer for The Simpsons, who has used the pseudonym Penny Wise
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