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Lester was born in Evanston, Illinois but has moved around the United States making homes in New York City, San Francisco, Chicago, Minneapolis and finally settling in Pawling, New York with her husband.
As a girl, Lester dreamed of getting married but never of being a writer. She became an elementary school teacher, got married and had two sons. After her sons were born, Lester took time off as a teacher and began writing children's literature. Her works are mainly influenced by her old second-grade students who helped produced characters such as Tacky the Penguin, Pinkerton the Pig and Fragility the Hippopotamus.
Lester's first children's book was published in 1979 and her writing career took off from there. She has now published more than two dozen books.
Lester has also illustrated a few of her own books, but typically illustrator Lynn Munsinger has produced the illustration for Lester's books. Lester and Munsinger have collaborated on over a dozen children books.
Beyond writing, Lester spends time traveling the country, visiting schools and encouraging children to write. She has also written Author: A True Story (Houghton Mifflin, 1997; ISBN 0395827442, LCCN 96-9645), directed towards young writers and based on her school visits and the editing process as a writer.
- Tacky the Penguin (1990)
- Three Cheers for Tacky (1996)
- Tacky and the Emperor (2002)
- Tackylocks and the Three Bears (2004)
- Tacky in Trouble (2005)
- Tacky and the Winter Games (2007)
- Tacky goes to Camp (2009)
- A Porcupine Named Fluffy (1986)
- The Wizard, the Fairy, and the Magic Chicken (1988)
- It Wasn't My Fault (1989)
- Pookins Gets Her Way (1990)
- Me First (1995)
- Wuzzy Takes Off (1995)
- Princess Penelope's Parrot (1996)
- Listen Buddy (1997)
- Author: A True Story (2002)
- Hooway for Wodney Wat (2002)
- Score One for the Sloths (2003)
- Something Might Happen (2003)
- Batter Up Wombat (2006)
- Hurty Feelings (2007)
- The Sheep in Wolf's Clothing (2007)
- Wodney Wat's Wobot (2011)
- Lester, Helen. Author: a True Story. Houghton Mifflin Children's Books. 1997.