He began his career as a freelance, writing for Melody Maker in the early 1990's, as well as City Limits, 20/20 (magazine), Sky Magazine and The Jewish Chronicle. During this time he covered grunge, shoegazing, and the Madchester and Britpop scenes, touring extensively with bands, both in the UK and abroad.

In 1993, Lester was made Features Editor of Melody Maker, and in 1997 left to help launch the monthly music and film magazine, Uncut with Allan Jones, where he stayed as Deputy Editor until 2006.

Lester has written over a dozen rock and pop biographies, has co-authored the Virgin Encyclopedia of Albums, and regularly appears on radio and TV as a music pundit. He has interviewed hundreds of musicians and actors, from Kylie to Janet Jackson, and Mick Jagger to Snoop Dogg, and has written sleevenotes on everyone from Todd Rundgren to Hall & Oates, The Smiths and The Sex Pistols.

He currently lives in Bushey, Hertfordshire, where he has been working since January 2007 as a freelance, contributing to many publications, including the Guardian newspaper, (where he writes the universally despised 'New Band Of The Day' feature and does the daily 'Critics Picks'), The Sunday Times, the Daily Express, The Mail on Sunday, The Daily Telegraph, The Scotsman, Q , GQ , Record Collector and The Jewish Chronicle, where he writes about life as a divorced dad of three called 'Unsurprisingly Suddenly Single'.

In 2008, Lester won the 'Breaking Music Writer' award at the Record of The Day Awards for Music Journalism and PR for his 'New Band of the Day' column in the Guardian.