Dress To Kill, Eddie's 5th live show, marked his breakthrough in the USA and Canada. In February 1998 Eddie took the show to Stamford, the Aspen Comedy Festival, where he won the Jury Award for "Best One-man Show", to Toronto and to the Westbeth Theatre Center in New York, where he played to packed houses for 4 months, from March to July. He returned to the USA in September that year, where he performed the show in San Francisco and Los Angeles. The shows were promoted by Robin Williams and were seen by celebrities such as Eric Idle, Steve Martin, George Harrison, Carrie Fisher, Madonna, Gabriel Byrne, and Ellen Barkin.

It was during this tour that Eddie wrote the book, Dress To Kill with David Quantick, with photographs by Steve Double. The book was published by Virgin Books in hardback in 1998 and in paperback in 2000.

In Dress To Kill, Izzard reflects on his birth in Yemen and his childhood in Northern Ireland, Wales and London, and muses on animals, male tomboys, street theatre, sex, crime, God, The Great Escape, Bible stories starring Sean Connery and James Mason, and cats who dig for oil. He also reflects on the trials and tribulations of being a cross-dressing surrealist comedian intent on making it in America.