Henry Goodman won a Laurence Olivier Award for his sensitive performance as Shylock in Trevor Nunn's brilliant production of The Merchant of Venice at the National Theatre in 2000. Goodman's landmark performance (immortalized on video) managed to find a startling poignancy in the character while never making any apologies for the anti-Semitic tone of the play. Edmund Kean played the role as an inhuman monster, but Goodman managed to turn him into a heartbreakingly human monster. The audience was stunned as his unremitting demand for his pound of flesh, but the cruelty of his bond seems justifiable through his treatment throughout the play. And when the tables are turned in the trial scene, Goodman eschewed the histrionics that many actors indulge in and accepts his fate with a grim reality - since he doesn't weep for himself, we feel free to weep for him. The Evening Standard wrote "Goodman performance is shot through with surprises…It's Goodman's night. His Shylock proves a magnificent victim of the revenge principle."

Goodman has excelled in classical roles like Malvolio and Tartuffe, but he has also had success in musicals like Assassins, Chicago, and Fiddler on the Roof. One of his most publicized engagements was when he was hired to replace Nathan Lane in the Broadway production of The Producers, but nervous producers were so dissatisfied with Goodman's interpretation of Max Bialystock that they removed him before reviewers had a chance to see his performance. Preview audience reported that his portrayal was very amusing, although much darker than the Tony-winning Lane who had created a sensation in the role. Goodman was replaced with Lane's understudy Brad Oscar, who did a virtual Nathan Lane impression in the part, illustrating that the producers weren't interested in a unique interpretation of the character.

Donald Wolfit (1902-1968) was a powerful if volatile talent, who provided the basis for the imperious Sir in the Ronald Harwood play The Dresser. Opinions of his abilities were mixed; he was savaged by critics on his only American tour in 1947 but he was highly esteemed in his own country and knighted in 1957. Wolfit gave landmark performances as Tamburlaine, Oedipus, and Volpone; but his life's work was presenting Shakespeare, achieving notoriety at Stratford and then touring nonstop with his own company beginning in 1937. He played most of the great Shakespearean roles and was memorable as Richard III, Othello and Hamlet, but by far his greatest role was King Lear, which held the central place in his repertoire for over ten years. The legendary critic James Agate said "Mr. Wolfit had and was all the things we demand, and created the impression Lear calls for. I will deliberately say that his performance on Wednesday was the greatest piece of Shakespearean acting I have seen since I have been privileged to write for the Sunday Times."

Derek Jacobi made his first attempt at Richard II for television in a memorable performance for the BBC's series of the Shakespearean canon in 1979. Fresh from recent triumphs like his Hamlet for the Prospect Theatre Company and his television role in I, Claudius, Jacobi's arrogant monarch (opposite John Gielgud as John of Gaunt and Janet Maw [pictured] as Queen Isabel) was considered (along with Bob Hoskins' Iago and Jacobi's Hamlet) as one of the few truly memorable performances in the BBC's ambitious, if uneven, enterprise.

Jacobi returned to the role in 1988 in a production directed by Clifford Williams at the Phoenix Theatre in London, and his performance had grown by leaps and bounds in the intervening decade. Kenneth Hurren wrote in Mail on Sunday "Seek not Shakespeare at the National Theatre. The Bard flourishes now in the West End, where Derek Jacobi gives the performance of his life. Forgivably, the production can find no dramatic excitement in the politics and family squabbles. Everything depends on Jacobi. Not for him the wimpishness or effeminacy that some actors misguidedly thrust upon Richard. He is conniving, devious and arrogant, yet he loses none of the final pathos, captures all the music of the verse and is, in short, magnificent."

William Charles Macready (1793-1873) is considered by some historians as the first "modern" actor who was legendary as introducing the pause for dramatic effect. He enjoyed success as Macbeth (his favorite role), Wolsey, Marc Antony, Richard III, Coriolanus and King John, but he was famous for playing tragic roles based on paternal love (particularly in Sheridan Knowles' Virginius, one of the theatrical staples of nineteenth century actor-managers). Macready first played Lear successfully in Nahum Tate's version in 1834, but in 1838 he staged a production that employed a fully Shakespearean text and contained the first appearance of the Fool in over a century (although it eliminated half the lines of Shakespeare's text and retained Tate's reordering of the scenes of the last three acts.) John Forster approved, writing "Mr. Macready's Lear, remarkable before for a masterly completeness of conception, is heightened by the introduction of the Fool to a remarkable degree. It accords exactly with the view he seeks to present of Lear's character."

Macready is best remembered for his part in the notorious Astor Place riot in 1849, which sprang from a rivalry that grew between the English-born Macready and the first great American-born stage star Edwin Forrest, during Macready's tours of the United States. it came to a head during Macready's performance of Macbeth at the Astor Opera House in Manhattan on May 7, 1849 when Forrest's supporters began throwing refuse that they had brought with them at Macready. He announced plans to leave the city but was talked out of it by a group of prominent New Yorkers and agreed to continue the tour. That night, up to 10,000 people filled the streets around the theater by the time the play opened at 7:30. Troops arrived later that night and were attacked by the crowd forcing them to open fire, first in the air and then point blank at the rioters. In the end, between 22 and 31 rioters were killed, 48 were wounded, and Macready left the country in disguise. The tragic event is the subject of the play Two Shakespearean Actors in which Brian Bedford played Macready and Victor Garber played Forrest.

Ian Holm (1931-2020) was a stalwart member of the RSC for fourteen years, winning acclaim for his performances of Puck and Prince Hal, an Evening Standard Award for his 1967 performance of Henry V and a Tony Award the same year for Harold Pinter's The Homecoming. He played Richard, Duke of Gloucester in The Wars of the Roses, the Royal Shakespeare Company's massive landmark compendium of the three Henry VI plays and Richard III directed by Sir Peter Hall for the RSC in 1963 and preserved on television in 1965. Bernard Levin of the Daily Mail called the production "a landmark and a beacon in the post-war English theatre, a triumphant vindication of Mr. Hall's policy, as well as his power as a producer." The outstanding performances were considered to be Peggy Ashcroft's Margaret and Holm's Richard, despite his initial feeling that the production would meet with little success. Ultimately, his evolution from the the cunning guttersnipe in the Edward IV segment of the production into the snickering psychopath of Richard III became one of the great tour de forces in the history of the RSC.

Holm eventually retired from theater to focus on his successful movie career. Although he had received an Oscar nomination for Chariots of Fire and appeared in such noteworthy films as The Sweet Hereafter, The Fifth Element and as Polonius in Franco Zeffirelli's Hamlet starring Mel Gibson (the only reference you will find to that performance in this list), he will forever be remembered as Bilbo Baggins in Peter Jackson's Lord of the Rings films, a part Holm won by virtue of his performance as Frodo in the BBC radio adaptation of the Tolkien novels. Holm's last acting role was as Bilbo in Jackson's prequel The Hobbit: The Battle of the Five Armies, a fitting finale to a brilliant career.

Peggy Ashcroft (1907-1991) said she agreed to take on the role of Margaret of Anjou in The Wars of the Roses, the Royal Shakespeare Company's massive 1963 presentation of the three parts of Henry VI (edited to be presented in two performances) and Richard III because she was attracted to the "problem of presenting with credibility a woman who could carry her lover's severed head on to the stage and play a scene holding it in her arms." Ashcroft not only performed the scene with credibility, but she was acclaimed as one of the best things in Peter Hall and John Barton's landmark production which proved a marathon for the actors, especially on Saturdays when the cycle was performed in its entirety beginning at 10:30 in the morning and not being completed until 11:00 that night. Critics were particularly lavish in their praise of Ian Holm as the Duke of Gloucester (later Richard III) and David Warner as Henry VI, but the consensus was that Ashcroft's Margaret was the jewel in the crown of the RSC's landmark achievement, with many calling it the finest work of her blue chip career.

Ashcroft seldom performed in Shakespeare after The Wars of the Roses, her only appearance being as Queen Catherine in the rarely-performed Henry VIII for the RSC in 1969. But she made a remarkable return to the Bard's work in 1981 when she had a success as the Countess of Rousillon in Trevor Nunn's brilliant production of All's Well that Ends Well at the age of 74.

Charles Macklin (c. 1699-1797) was one of the most volatile actors who ever lived, having infamously killed another actor in a dispute over a wig in the Drury Lane green room in 1735 and successfully suing the leaders of an audience riot who pressured the management of Drury Lane to fire him after he replaced a favorite actor in the role of Macbeth. But he was one of the greatest actors of his era, best known for his performance of Shylock which rejected the tradition of depicting the role as a comic figure and instead imbuing him with a tragic aura. Macklin's naturalistic approach bordered on Method Acting, as he immersed himself in Jewish culture in preparation for the role and his subsequent performance revolutionized all theories about the play and had a major impact on the way Shylock would be played forever afterwards. He debuted in the role on Feb. 14, 1741 and would continue playing it until 1789, when he was forced to withdraw from a benefit performance in the first act due to failing memory and have his understudy complete the performance. But his Shylock would be considered definitive until the advent of Henry Irving, with the poet Alexander Pope famously writing of Macklin's portrayal, "This is the Jew that Shakespeare drew.”

Charles Laughton (1899-1962) was the hottest actor in England following his Oscar-winning performance in The Private Life of Henry VIII when he joined the Old Vic in October of 1933 to play such roles as Macbeth, Prospero, and the title role in Shakespeare's Henry VIII. He felt the latter production was a mistake as audiences inevitably compared it to the film, but there was no doubt about his one great triumph of the season, Angelo in Measure for Measure. The London Times said "We are given the man of affairs, smiling, precise, and self-confident as well as the sensualist, and Mr. Laughton sees to it that what is horrible in the overwhelming of a formidable talent by the senses is given its full value. But throughout the evening this performance is rich and satisfying, full of subtle penetration and expressive gesture."

Laughton's Angelo was considered the model of how the role should be played until John Gielgud offered his definitive interpretation at Stratford in 1950. Yet despite notable stage successes in Galileo, Don Juan in Hell and Major Barbara (all of which he also directed), Laughton did not return to Shakespeare until 1959, when (in deteriorating health) he unsuccessfully took on King Lear and Bottom in A Midsummer Night's Dream (pictured). The latter was filmed (at great expense and at Laughton's urging) for NBC television in the USA, although it was never broadcast.

Ian McKellen wrote that "When in 1989 the Royal Shakespeare Company’s ex-artistic director Trevor Nunn suggested a production of Othello as the last production at the old tin hut called 'The Other Place' in Stratford-upon-Avon, the management hesitated, even though the renowned opera baritone Willard White was to make his dramatic debut as the Moor. It was rumoured that Nunn paid for the stage production and eventually for part of the costs to make a video version." The production was a reunion for McKellen and Nunn who had last worked together on their 1976 presentation of Macbeth, one of the greatest Shakespearean productions of the 20th century. Othello didn't quite live up to that tradition, as White (who had no Shakespearean acting experience), while physically suited to the role and possessing a formidable speaking voice, was somewhat stiff and labored in his performance of the Moor.

McKellen, however, was magnificent in his first full-scale Shakespearean part since his 1978 performance as Sir Toby Belch, having devoted most of the previous decade to his one-man Shakespeare pastiche Acting Shakespeare. He made Iago a by-the-book NCO, and his punctiliousness won him the Evening Standard Award and the London Critics' Circle Award. Robert Smallwood wrote in The Shakespeare Quarterly, "Every moment, every gesture of [McKellen's] performance seemed precisely calculated to the realization of an extraordinary, psychotic personality. This was a military man through and through, a hard-bitten NCO who, one felt, had always been in the army. ... At the end his bearing remains unchanged, the order to 'Look on the tragic loading of this bed' obeyed with the usual straight-backed step forward and then a stare of cold, detached, emotionless curiosity, the last thing we see as the lights go out."

When Patrick Stewart first played Claudius in 1980, he was a relatively unknown member of the Royal Shakespeare Company whose only previous experience with the play was in his third appearance for the RSC in 1966, as a replacement for the Player King in the closing performances of David Warner’s Hamlet in London. Stewart’s star gradually rose in the years since, winning praise for his Shylock and an Olivier Award for his Enobarbus in Peter Brook’s 1979 production of Antony and Cleopatra, as well as international acclaim for his appearance as the Roman soldier Sejanus in the miniseries I, Claudius.

Stewart’s position at the RSC was such that he was assigned the role of Claudius in the BBC production of Hamlet that was part of the ambitious Complete Dramatic Works of William Shakespeare. The Melancholy Dane was portrayed by Stewart’s I, Claudius co-star Derek Jacobi, already regarded as one of the greatest Hamlets of the century by virtue of his stage performance with the Prospect Theatre Company; and Stewart matched the great Shakespearean in a performance of staggering power and humanity that projected a strength and maturity that belied the chronological difference in the age of the two actors (Jacobi is actually two years older than Stewart). Jacobi is an unforgettable Hamlet in the production - by far the finest episode of the series - but Stewart makes no less of an impression in his understated performance – arguably the most memorable depiction of the role in the play’s history.

When Stewart returned to the part in 2008, he was one of the most famous actors in the history of the RSC by virtue of his appearances in Star Trek: The Next Generation and the X-Men film franchise. He had continued to make memorable (and occasionally historic) performances in Shakespeare, as Marc Antony, Prospero, Othello, and an Evening Standard Award-winning Macbeth, when he opted to revive his Claudius at the RSC’s Courtyard Theatre. The production was a sell-out after it was announced that Stewart’s Hamlet would be science fiction cohort David Tennant, star of the long-running BBC institution Dr. Who. While Tennant failed to rise to the immortal peaks that Jacobi lofted to as Hamlet (due, in part, to his suffering a back injury that limited his appearances during the London run), he was generally acclaimed in the role. It was Stewart, however, who nabbed his third Olivier Award for the production (after his Enobarbus and his acclaimed one-man performance in A Christmas Carol), in which he also played Hamlet’s father’s ghost. Charles Spencer wrote in The Telegraph, “I have no reservations at all about Stewart, who delivers the strongest, scariest performance as Claudius I have seen. A modern tyrant in a surveillance state full of spies, informers and two-way mirrors in Doran's thriller-like production, he presents a façade of smiling, bespectacled geniality.”