He began with rendering his home town of San Francisco but has gone on to draw many U.S. cities including New York and Los Angeles, as well as international locations such as Paris, Rome, Amsterdam, Buenos Aires, Shanghai, Beijing, and Tokyo.

In 2016 Madonna released his first illustrated novel, Close Enough for the Angels, as a limited edition book at the Dryansky Gallery in San Francisco.

The book features fictional artist Emit Hopper, 'a one-hit wonder, twice' who, after twenty years, is having a comeback, only to have his wife go missing while hiking in the Yosemite wilderness.

The three volume box set saw Emit scouring Europe in search of the man responsible for his wife's disappearance.

Come to Light introduced a new character, Ronnie Gilbert, a former ex-San Francisco Police officer turned private investigator.

Madonna suffered multiple internal injuries, a brain bleed, a nicked carotid artery, lung collapse, and a shattered heel.

In 2018 Madonna partnered with Bay Area historian Gary Kamiya, whose Cool Gray City of Love was a best-seller.

[4] In contrast to his detailed pen and ink drawings of All Over Coffee, the series uses deliberately rudimentary characters, drawn in a quick, loose hand.