Simon was born in Oxford on 12 January 1959, the only child of Christopher Tolkien and his first wife, Faith Faulconbridge. His parents separated when he was five years old and he grew up with his mother. He was educated at the Dragon School in Oxford and then Downside School. He studied modern history at Trinity College, Oxford, after which he embarked on a fifteen-year career as a criminal lawyer. In 1984, he married Tracy Steinberg who was born in 1962. They have two children, a son Nicholas and a daughter Anna. Tracy owned and operated a vintage clothing store in Chelsea, London, called Steinberg & Tolkien, which shut in September 2007.
He became a barrister in 1994. In January 2000, he began writing fiction. His first novel, which he has described as a black comedy, was not accepted for publication. His second novel, a courtroom drama, was published in the United States as The Final Witness in 2002 and in United Kingdom as The Stepmother in 2003. His second published work, The Inheritance (the first of a trilogy featuring Inspector Trave of the Oxfordshire Criminal Investigation Department), was published in 2010. The second book of the Inspector Trave trilogy, The King of Diamonds, was released in 2011. The third and final book in the trilogy, Orders from Berlin, was released in 2012.
His 2016 novel, No Man's Land: a Novel, was released concurrent with the 100 year anniversary of the Battle of the Somme; the middle third of the novel is set in that months-long World War I battle. The novel follows the life of a poor English child / young adult (Adam Raine), beginning with episodes of labor unrest in London and on to the strikes in coal mining communities, class distinctions, and home front experiences of WWI. Simon Tolkien acknowledges that the experiences of Adam Raine only superficially resemble those faced by his grandfather (J. R. R. Tolkien) in the same large long battle of the war, but he wanted to write something that in part paid tribute to his grandfather's pivotal war experience as a young man, only a few years older than the age of the protagonist of No Man's Land.
Simon Tolkien notably disagreed with the policy of his grandfather's estate in regard to The Lord of the Rings films. When Christopher Tolkien issued a statement that the "Tolkien estate would be best advised to avoid any specific association with the films", Simon Tolkien broke ranks, offering to cooperate with the filmmakers, stating "It was my view that we take a much more positive line on the film and that was overruled by my father." Following up a 2001 interview with the Independent, Simon in 2003 gave interviews to the Daily Telegraph and other media in which he discussed his strained relationship with his father, describing it as a permanent breach. However, they have since reconciled.
Inspector Trave novels
- The Inheritance (2010)
- The King of Diamonds (2011)
- Orders from Berlin (2012)
- Final Witness/The Stepmother (2002)
- No Man's Land (2016)
- Hough, Andrew (2012-11-18). "Simon Tolkien: J R R Tolkien's grandson admits Lord of the Rings trauma". Sunday Telegraph. Retrieved 2012-12-15.
- "J.R.R. Tolkien Encyclopedia". google.com.
- David Thomas (24 February 2003). "A leaf torn from the family tree". Telegraph.co.uk.
- "The Classic Fat Cat Tale". Susanna Lau. 4 August 2007. Retrieved 16 December 2014.
- "Simon Tolkien". BBC News. 2003-12-17. Retrieved 2009-07-18.
- Flynn, Gillian (2003-12-17). "Final Witness". Entertainment Weekly. Retrieved 2009-07-18.
- "From Mordor to murder: Another Tolkien hits the books". tribunedigital-chicagotribune.
- "Book review: 'The King of Diamonds,' by Simon Tolkien". dallasnews.com.
- "Fiction Book Review: Orders from Berlin by Simon Tolkien". PublishersWeekly.com.
- Duncan, Hugo (2003-12-09). "From Mold to Middle Earth". Daily Post. Retrieved 2009-07-18.
- Susman, Gary (2001-12-10). "Tolkien Opposition". Entertainment Weekly. Retrieved 2009-07-18.
- Thomas, David (2003-02-24). "J R R Tolkien's grandson 'cut off from literary inheritance'". Sunday Telegraph. Retrieved 2010-04-23.
- Sandy Brawarsky (6 June 2017). "J.R.R. Tolkien's Jewish Great-Grandson Has A Play On Terezin". The Jewish Week. Times of Israel.
- Michael Kaminer (26 June 2017). "A Tolkien Takes On The Holocaust". The Forward.