Starkey was educated at Kendall Grammar School and Fitzwilliam College Cambridge where he obtained a BA degree and a PhD. He then was a Research Fellow at Fitzwilliam College Cambridge (1970-72), and a lecturer in history in the Department of International History at the London School of Economics (1972-98). From 1998 he has been visiting fellow at Fitzwilliam College Cambridge.

He has contributed articles and written collumns for various newspapers and magazines including "The Sunday Times" and "Spectator". Starkey has been a regular panelist on the BBC Radio 4 programme The Moral Maze and it was during this time that the description "...the rudist man in Britain" was used on the front page of the Daily Mail. There has also been a version on BBC 2 television. From 1995 to 1998 he was a presenter on Talk Radio. He has been a writer a presenter of several television series.

Since 1980 Starkey has been on the Editorial Board of History Today. He has been on the Commemorative Plaques Working Group for English Heritage since 1993; president of the Society for Court Studies since 1996; patron of the Tory Campaign for Homosexual Equality (TORCHE) since 1994, and an honorary associate of the Rationalist Press Association since 1995.

His success with his media work and associated books made him wealthy and allowed him to fund further work through the company Jutland. The computerisation of the inventory of possessions of Henry VIII is funded equally between himself and the Society of Antiquarians.

Starkey gave up his teaching at the London School of Economics in 1998 to concentrate on his other work. He is the UK's leading constitutional and monarchy expert and a colourful media personality. David currenly writes diary columns for The Sunday Times and The Spectator and appears frequently on television and radio.