Possessing a sort of angelic quality that adds the dimension of spoiled innocence to his often sinister or nasty roles, the actor made a memorable film debut in 1996's "Some Mother's Son", portraying a cold and contemptible Thatcherite in this fact-based tale about the hunger strike protest launched by IRA prisoners in troubled Northern Ireland. That same year, he was featured in the more lighthearted "True Blue", another true story, this about a 1987 Oxford University boat race. After gracing the small screen as Saffron's insufferably controlling fiancé Paolo in the 1997 TV-movie "Absolutely Fabulous: The Last Shout" (BBC and Comedy Central), Hollander went on to deliver another enjoyable scene-stealing turn as a flamboyant gay man carrying on a strange, secret affair with a real estate agent in Rose Troche's "Bedrooms and Hallways" (1998). A small independent film, it played the festival circuit but failed to find much support in its theatrical release, doing little to raise the actor's profile despite his outstanding work. Similarly, the romantic comedy "Martha - Meet Frank, Daniel & Laurence" (1998, released in the USA as "The Very Thought of You" in 1999) proved a moderate success in his homeland but was quickly relegated to the video shelves in America. Still, Hollander acquitted himself as another larger-than-life character, the wealthy music executive Daniel. He followed with yet another strong supporting role in Ben Elton's "Maybe Baby" (lensed 1999), starring Hugh Laurie and Joely Richardson as a screenwriter and his wife attempting to conceive.
A contemporary of Sam Mendes at Cambridge University, Hollander worked with the famed theater director at the groundbreaking Donmar Warehouse. His notable stage credits have included an appearance in "The Threepenny Opera", and starring turns in Almeida productions of "Tartuffe" (1996) and "The Government Inspector" (1997). Jez Butterworth's play "Mojo" added yet another baby-faced psychopath to the actor's resume. Critics were divided over Hollander's interpretation of Lord Alfred Douglas in David Hare's controversial portrait of the betrayal of Oscar Wilde, "The Judas Kiss" (1998). Originating the part at the Almeida opposite Liam Neeson, he found the requisite arrogance in the role but many British reviewers felt he lacked the necessary charm. Broadway audiences and critics, however, were less harsh in their evaluation, recognizing that the cherubic actor was adding yet another monster to his gallery of stage roles. Back in the feature world, Hollander had a supporting role in the period comedy, "The Clandestine Marriage" (1999), then played a homosexual restaurant owner who begins a romance with a high-spirited young woman after losing his male lover in the British comedy, "The Lawless Heart" (2001).
In Robert Altman's ensemble comedy of upstairs meets downstairs wrapped in a murder mystery, "Gosford Park" (2001), Hollander was on the list of suspects at a British country estate accused of murdering the manor's patriarch during a weekend of hunting. After a supporting role in "Enigma" (2001), a rather dull period thriller about the cryptologists of Britain's Bletchley Park who crack the Nazi enigma code, he played Mr. Mantalini in a small screen rendition of Charles Dickens' "Nicholas Nickleby" (Bravo, 2001). An appearance in Neil LaBute's uneven period romance "Possession" (2002) was followed by the made-for-TV movie, "Cambridge Spies" (BBC Television, 2003), in which Hollander played Guy Burgess, one of four Cambridge students sent by MI5 to the Soviet Union during World War II as spies to fight the Nazis, only to emerge decades later as loyal Communists. In Masterpiece Theatre's "The Lost Prince" (BBC, 2004), he played the absentee King George V whose son, Prince John, was never a contender to the throne because of epilepsy.
Following a small role in Richard Eyre's "Stage Beauty" (2004), a period comedy about King Charles II's decision to allow women to perform onstage in 17th century England, thus putting a former leading lady (Billy Crudup) out of work, Hollander played a tabloid photographer in the cartoonish revenge thriller, "Paparazzi" (2004). He returned to period romance with the critically acclaimed adaptation of Jane Austen's "Pride and Prejudice" (2005), giving a subtly comic performance as the dull vicar, William Collins, whose betrothal to Charlotte Lucas (Claudie Blakely) comes as a shock to her best friend, Lizzy Bennet (Keira Knightley).