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Her first book, My Horizontal Life: A Collection of One-Night Stands (2005), describes the variety of sexual encounters she has experienced throughout her life. It's Me, Chelsea (2008), a collection of humorous essays, hit the top of The New York Times Nonfiction Best Seller List on May 11, 2008, On November 15, 2010, it was announced that Handler's publishers gave her her own publishing imprint, Borderline Amazing/A Chelsea Handler Book.
She also signed a three-book deal with the imprint, the first of which is called Lies That Chelsea Handler Told Me, where her coworkers and family members discuss their experiences with Handler, which was released in May 2011 and also hit the top of the bestseller list.
The same year, a leaked sex tape of Handler was being offered for sale.
After news of it became public, Handler said on Chelsea Lately the tape "was made as a joke" more than 10 years earlier, adding, "I put it on an audition tape for a comedy club, because I'm a comedienne, and I've been showing it at birthday parties for fucking years." In a 2011 interview in The New York Times, Handler revealed that she had an abortion when she was 16, saying she had the procedure "because that's what I should have done. Anyway, those are things that people shouldn't be dishonest about." Handler was a vocal supporter of the 2016 presidential candidate Hillary Clinton and was critical of her opponent Donald Trump.
In July 2010, during a tour stop in Salt Lake City, Handler took part in the "I Am Equal" photo documentary project in memory of her mother, Rita, who died from complications of cancer.
Along with her photo being added to the documentary and accompanying photo mosaic, she also shared a "Photo Story" with a message that inspires people to take chances in life.
Handler said she envisioned a show more serious than Chelsea Lately: "I would like a healthy mix of everything that goes on around the world, mixed with interesting stuff in our country.