In The Merchant of Venice, Shylock is a Jewish moneylender who lends money to his Christian rival, Antonio, setting the security at a pound of Antonio's flesh. When a bankrupt Antonio defaults on the loan, Shylock demands the pound of flesh, as revenge for Antonio having previously insulted and spat on him. Meanwhile, his daughter, Jessica, elopes with Antonio's friend Lorenzo and becomes a Christian, further fuelling Shylock's rage. She also takes money and jewels from Shylock.
During Shakespeare's day, money lending was a fairly common occupation among Jews. This was due in part to Christians staying out of the profession due to their belief that usury – at that time considered to mean charging interest of any kind on loans – would be a sin.
Jacob Adler and others report that the tradition of playing Shylock sympathetically began in the first half of the 19th century with Edmund Kean, and that previously the role had been played "by a comedian as a repulsive clown or, alternatively, as a monster of unrelieved evil." Kean's Shylock established his reputation as an actor.
From Kean's time forward, many actors who have played the role — with the notable exception of Edwin Booth, who played him as a simple villain — have chosen a sympathetic approach to the character; even Booth's father, Junius Brutus Booth, played the role sympathetically. Henry Irving's portrayal of an aristocratic, proud Shylock (first seen at the Lyceum in 1879, with Portia played by Ellen Terry) has been called "the summit of his career". Jacob Adler was the most notable of the early 20th century, playing the role in Yiddish in an otherwise English-language production.
Kean and Irving presented a Shylock justified in wanting his revenge; Adler's Shylock evolved over the years he played the role, first as a stock Shakespearean villain, then as a man whose better nature was overcome by a desire for revenge, and finally as a man who operated not from revenge but from pride. In a 1902 interview with Theater magazine, Adler pointed out that Shylock is a wealthy man, "rich enough to forgo the interest on three thousand ducats" and that Antonio is "far from the chivalrous gentleman he is made to appear. He has insulted the Jew and spat on him, yet he comes with hypocritical politeness to borrow money of him." Shylock's fatal flaw is to depend on the law, but "would he not walk out of that courtroom head erect, the very apotheosis of defiant hatred and scorn?"
Some modern productions take further pains to show how Shylock's thirst for vengeance has some justification. For instance, in the 2004 film adaptation directed by Michael Radford and starring Al Pacino as Shylock, the film begins with text and a montage of how the Jewish community is abused by the Christian population of the city. One of the last shots of the film also brings attention to the fact that, as a convert, Shylock would have been cast out of the Jewish community in Venice, no longer allowed to live in the ghetto, and would still not be accepted by the Christians, as they would feel that Shylock was yet the Jew he once was. Another interpretation of Shylock and a vision of how "must he be acted" appears at the conclusion of the autobiography of Alexander Granach, a noted Jewish stage and film actor in Weimar Germany (and later in Hollywood and on Broadway). Granach 1945; 2010, 275-279.
Arnold Wesker's play The Merchant tells the same story from Shylock's point of view. In this retelling, Shylock and Antonio are friends bound by a mutual love of books and culture and a disdain for the anti-Semitism of the Christian community's laws. They make the bond in defiant mockery of the Christian establishment, never anticipating that the bond might become forfeit. When it does, the play argues, Shylock must carry through on the letter of the law or jeopardize the scant legal security of the entire Jewish community. He is, therefore, quite as grateful as Antonio when Portia, as in Shakespeare's play, shows the legal way out. The play received its American premiere on November 16, 1977 at New York's Plymouth Theatre with Joseph Leon as Shylock, Marian Seldes as Shylock's sister Rivka and Roberta Maxwell as Portia. This production had a challenging history in previews on the road, culminating (after the first night out of town in Philadelphia on September 8 1977) with the death of the Broadway star Zero Mostel, who was initially cast as Shylock. The play's author, Arnold Wesker, wrote a book chronicling the out-of-town tribulations that beset the play and Mostel's death called "The Birth of Shylock and the Death of Zero Mostel."
The award-winning monologue Shylock (play), by Canadian playwright Mark Leiren-Young, focuses on a Jewish actor named Jon Davies, who is featured as Shylock in a production of Shakespeare’s The Merchant of Venice. Jon addresses his audience at a “talk back” session, after the play is closed abruptly due to controversy over the play’s alleged Antisemitism. Davies is portrayed both in and out of character, presenting and stripping down the layers between character and actor. Composed in one 80-minute act, it premiered at Bard on the Beach on August 5, 1996 where it was directed by John Juliani and starred popular Canadian radio host, David Berner. Its American debut was in 1998 at Philadelphia’s Walnut Street Theatre where it was directed by Deborah Block, starred William Leach and was “Barrymore Recommended.” It has since been produced at theatres, Shakespeare Festivals and Fringes throughout Canada and the US (including the San Diego Repertory Theatre where it was staged opposite a controversial production of The Merchant of Venice), was translated for a production in Denmark and has been staged twice by the original actor, Berner, in Venice.
Notable actors who have portrayed Shylock include Richard Burbage in the 16th century, Charles Macklin in 1741, Edmund Kean in 1814, William Charles Macready in 1840, Edwin Booth in 1861, Henry Irving in 1880, George Arliss in 1928, John Gielgud in 1937, Laurence Olivier at the Royal National Theatre in 1972 and on TV in 1973, Patrick Stewart in 1965 at the Theatre Royal, Bristol and 1978, plus (as Shylock) in a one-man stage show Mr. Stewart developed entitled "Shylock: Shakespeare's Alien" in 1987 and 2001, Al Pacino in a 2004 feature film version as well as in Central Park in 2010, and F. Murray Abraham at the Royal Shakespeare Company in 2006.
The play is frequently staged today, but is potentially troubling to modern audiences due to its central themes, which can easily appear antisemitic. Critics today still continue to argue over the play's stance on antisemitism.
The character's name has become a synonym for loan shark, and as a verb to shylock means to lend money at exorbitant rates. In addition, the phrase "pound of flesh" has also entered the lexicon as slang for a particularly onerous or unpleasant obligation.
English society in the Elizabethan era has been described as antisemitic. English Jews had been expelled in the Middle Ages and were not permitted to return until the rule of Oliver Cromwell. Jews were often presented on the Elizabethan stage in hideous caricature, with hooked noses and bright red wigs, and were usually depicted as avaricious usurers; an example is Christopher Marlowe's play The Jew of Malta, which features a comically wicked Jewish villain called Barabas. They were usually characterized as evil, deceptive, and greedy.
During the 1600s in Venice and in some other places, Jews were required to wear a red hat at all times in public to make sure that they were easily identified. If they did not comply with this rule they could face the death penalty. Jews also had to live in a ghetto protected by Christians, supposedly for their own safety. The Jews were expected to pay their guards. 
Readers may see Shakespeare's play as a continuation of this antisemitic tradition. The title page of the Quarto indicates that the play was sometimes known as The Jew of Venice in its day, which suggests that it was seen as similar to Marlowe's The Jew of Malta. One interpretation of the play's structure is that Shakespeare meant to contrast the mercy of the main Christian characters with the vengefulness of a Jew, who lacks the religious grace to comprehend mercy. Similarly, it is possible that Shakespeare meant Shylock's forced conversion to Christianity to be a "happy ending" for the character, as it 'redeems' Shylock both from his unbelief and his specific sin of wanting to kill Antonio. This reading of the play would certainly fit with the antisemitic trends present in Elizabethan England.
Hyam Maccoby argues that the play is based on medieval morality plays in which the Virgin Mary (here represented by Portia) argues for the forgiveness of human souls, as against the implacable accusations of the Devil (Shylock).
Many modern readers and theatregoers have read the play as a plea for tolerance as Shylock is a sympathetic character. Shylock's 'trial' at the end of the play is a mockery of justice, with Portia acting as a judge when she has no real right to do so. Thus, Shakespeare is not calling into question Shylock's intentions, but the fact that the very people who berated Shylock for being dishonest have had to resort to trickery in order to win. Shakespeare puts one of his most eloquent speeches into the mouth of this "villain":
Hath not a Jew eyes? Hath not a Jew hands, organs, dimensions, senses, affections, passions; fed with the same food, hurt with the same weapons, subject to the same diseases, heal'd by the same means, warm'd and cool'd by the same winter and summer as a Christian is? If you prick us, do we not bleed? If you tickle us, do we not laugh? If you poison us, do we not die? And if you wrong us, shall we not revenge? If we are like you in the rest, we will resemble you in that. If a Jew wrong a Christian, what is his humility? Revenge. If a Christian wrong a Jew, what should his sufferance be by Christian example? Why, revenge. The villainy you teach me, I will execute, and it shall go hard but I will better the instruction.—Act III, scene I
Alexander Granach, who played Shylock in Germany in the 1920s, writes, "...how does it happen that Shylock's defense becomes an accusation?...The answer must be a perfectly simple one. God and Shakespeare did not create beings of paper, they gave them flesh and blood! Even if the poet did not know Shylock and did not like him, the justice of his genius took the part of his black obstacle [Shylock, the obstacle to the plans of the young lovers] and, out of its prodigal and endless wealth, gave Shylock human greatness and spiritual strength and a great loneliness--things that turn Antonio's gay, singing, sponging, money-borrowing, girl-stealing, marriage-contriving circle into petty idlers and sneak thieves." (Granach 1945, 2010: 276-77)
Regardless of what Shakespeare's own intentions may have been, the play has been made use of by antisemites throughout the play's history. One must note that the end of the title in the 1619 edition "With the Extreme Cruelty of Shylock the Jew…" must describe how Shylock was viewed by the English public. The Nazis used Shylock for their propaganda. Shortly after Kristallnacht in 1938, The Merchant of Venice was broadcast for propagandistic ends over the German airwaves. Productions of the play followed in Lübeck (1938), Berlin (1940), and elsewhere within Nazi-occupied territory.
The depiction of Jews in the literature of England and other English-speaking countries throughout the centuries bears a strong imprint of The Merchant of Venice's Shylock. With slight variations much of English literature up until the 20th century depicts the Jew as "a monied, cruel, lecherous, avaricious outsider tolerated only because of his golden hoard".
It was not until the twelfth century that in northern Europe (England, Germany, and France), a region until then peripheral but at this point expanding fast, a form of Judeophobia developed that was considerably more violent because of a new dimension of imagined behaviors, including accusations that Jews engaged in ritual murder, profanation of the host, and the poisoning of wells. With the preduces of the day against Jews, atheists and non-Christians in general Jews found it hard to fit in with society. Some say that these attitudes provided the foundations of anti-semitism in the 20th century. "
Granach 1945: 276-277
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