Theatre
Lester received an Ian Charleson Award commendation and a Time Out Award for his 1991 performance as Rosalind in Cheek by Jowl's all-male production of As You Like It. In 1992 he played Paul in the UK premiere of John Guare's Six Degrees of Separation, alongside Stockard Channing at the Royal Court Theatre in a production that transferred to the West End's Comedy Theatre. The following year, he appeared as Anthony Hope in the National Theatre's production of Sweeney Todd: The Demon Barber of Fleet Street, receiving an Olivier Award nomination for Best Supporting Performance in a Musical. He has also appeared on stage as Robert in the Donmar Warehouse production of the Stephen Sondheim musical Company, for which he won an Olivier Award, and in the title role of Hamlet (Carlton TV Theatre Award).
In 2003, he played the title role in Henry V at the National Theatre.
In 2010, he played the part of Brick in Tennessee Williams' play Cat on a Hot Tin Roof at the Novello Theatre in London.
In 2012, he appeared as Ira Aldridge in the play Red Velvet, written by his wife Lolita Chakrabarti.
Lester played the part of Othello in the Shakespeare play of the same name in 2013 alongside Rory Kinnear as Iago at the National Theatre. Both actors won the Best Actor award in the Evening Standard Theatre Awards for their roles; the award is traditionally given to only one actor, but the judges were unable to choose between the pair.
In 2018, he played Sky Masterson in the Royal Albert Hall production of Guys and Dolls.
In 2021, he appeared in the live-streamed production of Hymn written by his wife Lolita Chakrabarti for the Almeida Theatre. The play co-starred Danny Sapani and was performed with social distancing in place in accordance with COVID-19 restrictions.
He made his Broadway debut in the 2021 production of The Lehman Trilogy, directed by Sam Mendes. His performance earned him a Tony Award nomination.
Lester made his debut with the Royal Shakespeare Company in 2025, playing the title character in Edmond Rostand's Cyrano de Bergerac at the Swan Theatre in Stratford-upon-Avon. In January 2026, it was announced that the production would be transferring to the Noel Coward Theatre in London's West End later in the year.
