Tom Hollander was born the second child of educated parents, both teachers. He grew up in Oxford, (UK).

Hollander credits the happy atmosphere of the Dragon School with his childhood introduction to acting. There, encouraged by an influential teacher named Andrew Roberts, he won the title role in "Oliver". His studies continued at Abingdon, as did his pursuit of acting. At about this point, he won a place in the National Youth Theatre, a UK organization for young people in the field of musical theatre, based in London, and later at the Children's Music Theatre. It was during CMT's "The Leaving of Liverpool" (1981) that he came to the attention of BBC television, and subsequently found himself front and center as the young protagonist in a well-regarded John Diamond (1981), based on the popular Leon Garfield adventure novel. He was just fourteen years old.

Other early projects included two roles in Bertholt Brecht's "The Caucasian Chalk Circle" (1985) for the National Youth Theatre, and "A Midsummer Night's Dream" for Oxford University Dramatic Society.

Hollander attended Cambridge University at about the same time as his childhood friend Sam Mendes in a visually bold (and well-remembered) staging of "Cyrano de Bergerac" (1988). Other collaborations with Mendes have followed, including work at the West End production of "The Cherry Orchard" (1989, with Judi Dench), and the Chichester Festival Theatre (1989) as well as a Toronto staging of "Kean" (1991) with Derek Jacobi. He also appeared in the Cambridge Footlights Revue (1988).

Upon graduation, Hollander hoped to gain entry to drama school, but found himself disappointed. The oversight did nothing to discourage a successful career already well under way: he garnered an Ian Charleson Award for his turn as Witwould in "The Way of the World" (1992), was nominated again for a "splendidly sinister, manic" performance as "Tartuffe" (1996), and yet again as a finalist for his Khlestakov ("a performance of ideal vigour and impudence"), in Gogol's "The Government Inspector" (1997). Inevitably, Hollander was urged to try films, and appeared in two films as early as 1996. True Blue (1996) (aka "Miracle at Oxford") found him in a small but memorable role as the cox for Oxford's noted 1987 "mutiny crew" that went on to win the that year's boat race against Cambridge, and in a thankless role in Some Mother's Son (1996), a sober drama about an IRA gunman, playing a Thatcher representative.