[1][2] Hollander gained attention portraying Mr. Collins in the 2005 Joe Wright film Pride & Prejudice, and as Lord Cutler Beckett in the Pirates of the Caribbean franchise.
Other film roles include Gosford Park (2001), Elizabeth: The Golden Age (2007), Valkyrie (2008), In the Loop (2009), Hanna (2011), About Time (2013), The Invisible Woman (2013), Mission: Impossible – Rogue Nation (2015), and Bohemian Rhapsody (2018).
[13] Sam Mendes, a friend and fellow student, directed him in several plays while they were at Cambridge, including a critically acclaimed production of Cyrano de Bergerac (which also featured future Deputy Prime Minister Nick Clegg).
In 1996 he made his Broadway debut acting in David Hare's The Judas Kiss portraying Lord Alfred Douglas opposite Liam Neeson as Oscar Wilde.
[26][27][28] In 2001 Hollander acted in Robert Altman's British murder mystery Gosford Park and Michael Apted's thriller Enigma.
Hollander has created several memorable comedic characters that draw more on his physical energy and intensity than his height, such as the "brilliantly foul-mouthed" Leon in BBC Two's Freezing, described in The Times as a "braying swirl of ego and mania".
He provided the vocal texture for Anthony Burgess' A Clockwork Orange recently with a "smooth, almost lyrical, crisp voice" that accomplished the task of rendering the extensive and unique slang of the book instantly understandable to readers.
[39] He also appeared in the TNT miniseries The Company as Kim Philby, having previously played Guy Burgess in the BBC's Cambridge Spies.
In 2008, Hollander made a notable cameo appearance as King George III in the HBO mini-series John Adams, and ended the year as a memorable Colonel Heinz Brandt in Valkyrie.
Hollander appeared in a lead role in Armando Iannucci's In the Loop as Secretary of State for International Development Simon Foster MP.
In 2010, Hollander and writer James Wood co-created the TV series Rev., a sensitive comedy about the all-too-human vicar of an inner-city parish.
[43] In 2010, Hollander returned to the live stage in a demanding comedic dual role in Georges Feydeau's A Flea in Her Ear at the Old Vic.
Playing both master and servant with "lightning physical precision and shockingly true confusion",[44] Hollander's was called "a virtuoso performance".
[45] Between September and November 2016 he starred as (a "career-best")[46] Henry Carr in Patrick Marber's "superb revival"[47] of Tom Stoppard's Travesties at the Menier Chocolate Factory.
The play (with the same cast) transferred to the Apollo Theatre in February 2017[1] and was nominated for five Olivier Awards including Best Actor (Hollander) and Best Revival (Travesties).
[48][49] In 2016 he played Lance "Corky" Corkoran in the AMC miniseries The Night Manager acting opposite Tom Hiddleston, Hugh Laurie, Olivia Colman, and Elizabeth Debicki.
[50] That same year he acted in the BBC / FX 2017 series Taboo playing the "inebriated and endearing, menacing and beguiling"[51] chemist, Dr George Cholmondeley.
[58][59] He has also portrayed the Russian artist Kazimir Malevich in Margy Kinmonth's documentary Revolution: New Art for a New World, which was released in the UK and Ireland in November 2016.
[67] In August 2014, he was one of 200 public figures who were signatories to a letter to The Guardian opposing Scottish independence in the run-up to September's referendum on that issue.