He began his career as a writer for the New Musical Express in 1977, later contributing to various publications including Uncut, Sight & Sound, The Wire, The Face, and The Guardian.
He began freelance work for various outlets, including The Face, Arena, the Sunday Times, The Independent, and the New Statesman.
In 1998, Penman published a compilation of his work entitled Vital Signs: Music, Movies, and Other Mania on Serpent's Tail to positive reviews.
Julia Kenna reviewed the book for Rolling Stone, commenting, Full of contradictions and witty one-liners, Penman uses language as an art form, playing with puns, synonyms, repetition, and punctuation for added effect... Two decades of politics, music and pop culture with a whip-smart wit and wisdom that draws you in and doesn’t let go.
[5] Penman has been cited as an influence by range of writers and theorists, including Simon Reynolds, Kodwo Eshun,[6] and Mark Fisher.