Life with My Sister Madonna is an autobiography by American artist, designer and interior decorator Christopher Ciccone and author Wendy Leigh.

Simon Spotlight Entertainment sold the book blindly to the retailers, with the expectation that it would create a media uproar for the contents and the nature of the memoir.

Ciccone reflects on working with Madonna, starting as a dancer for the music video for her 1983 single, "Lucky Star", to the Girlie Show in 1993.

He writes about Madonna's sex life, including her relationships with artist Jean-Michel Basquiat, actors Sean Penn and Warren Beatty, and director Guy Ritchie, alleging that the lattermost is homophobic.

[3] In June 2008, Simon & Schuster revealed that Christopher Ciccone had written a memoir on her, titled Life with My Sister Madonna.

"From the moment I found out that I wasn't doing Drowned World, to her and Guy's wedding, everything became a bit of a blur, a dark, fairly negative period of time for me," he felt.

[6] Ciccone explained to Chrissy Iley from the Irish Independent that Madonna had often tried manipulating him into working for free and forced him to perform tasks that he did not want.

[9] Ciccone would secretly arrive at Leigh's home in Key Biscayne, Florida, donning disguises (with the name Mr. Blake) lest anyone found about the project.

Barbara Ellen from The Observer called it Ciccone's "missed opportunity" at writing a "misery memoir", feeling a better title for the book would have been "Sissie Dearest".

Ellen ended the review saying that she felt the book was "an overlong, unintentionally hilarious essay on one brother's obsessive envy and resentment of his flawed but talented famous sister".

"[14] A similar review was written by Lee Randall from The Scotsman who added that "while this book is nothing if not self-serving, Ciccone does stop and examine his own ignoble behaviour and motives.

"[15] Alex Altman from Time noted that the memoir was focused less on Madonna but rather on Ciccone's life, self-described as the singer's "doormat".

[16] Giles Hattersley from The Times commended Ciccone's desire to release a tell-all memoir, but believed that he failed, since the majority of the book showed bitterness at never being better than Madonna.

Club found the book to follow the general theme of tell-all releases by someone bitter with Ciccone laying "out the case against his sister in a prosecutorial fashion", while involving their dead mother at any chance he got.

[18] Susanah Cahalan from the New York Post was mixed in her review, pointing out the highlight of the book as when Ciccone described the enmity he felt for Madonna's husband Guy Ritchie, by painting him as a homophobe.

Friedman found that the so-called revelations promised by Ciccone in the book appeared to be quite tame compared to the contemporary celebrity culture observed.

[24] Rosenberg clarified that Madonna realized her relationship with Ciccone was damaged irreparably, and that the release of the book ended any chance of the siblings ever reconciling.