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Pennywise is a character name in literature. It may refer to:
- In Stephen King's novel It, an evil creature sometimes appears in a form called Pennywise the Dancing Clown.
- In Charles King's novel A Trooper Galahad, he is Major Pennywise, a US Army paymaster.
- In Pennywise a comic play in Punch (magazine), volume 73, 1877, Pennywise Turniptop is a young wife.
- In W. H. M. Holmes's novel Oakleigh, or, The Minor of Great Expectations, Mark Pennywise is a trusty clerk.
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