Everyone around Mary is desperately trying to make Mary stop, but on this long day, Mary chooses instead to numb her pain to escape to a broken reality of the past. O’Neill uses Mary to show a relapse that in a matter of a day makes Mary insane from drowning in the morphine. James Tyrone is introduced to readers with two passions: love for his wife and his acting. O’Neill describes Tyrone, saying, “James Tyrone is sixty-five but looks ten years younger…He is by nature and preference a simple, unpretentious man, whose inclinations are still close to his humble beginnings and his Irish farmer forebears.” Tyrone’s first instinct is to fight makes him jump to anger instead of being a responsible parent. With his father deserting the family when he was only ten, Tyrone has no experience with model fathers and spends much of the day getting drunk, refusing to believe he has a problem. O’Neill writes in his stage directions ‘despite all the bourbon in him, he has not escaped.” Tyrone has plenty to want to escape from with a dying son, hatred of Jamie, and a drug addict wife. Just like Mary, Tyrone wants to hide from his problems described as ‘a sad, defeated old man, possessed by hopeless resignation.”
O’Neill exposes Tyrone as a hypocrite in his criticism of Mary. As an addict, he judges his wife’s coping mechanism without recognizing his own. On top of all of his other faults, James is a penny pincher and has made a habit of skimping on expenses for his families while indulging himself. Using a cheap doctor who prescribed morphine for his wife, Tyrone wants to repeat the cycle by choosing cheap medical care by sending Edmund to a state sanatorium to save money. By pushing his money into land, Tyrone pretends not to have enough money to comfortably support his family. Although Tyrone presents an appearance of being poor, the Tyrone men all drink bonded bourbon that has to age for years and is extremely expensive. Tyrone is only willing to splurge when he is the beneficiary. Ultimately, Tyrone’s desperation to have money has hurt him the most. He had a promising career as a Shakespearian actor who was receiving praise from Edwin Booth for his performance of Othello.
In taking the lead in a successful play, instead of improving his acting, he missed an opportunity for fame that led to his deep regret. Keeping Edwin Booth’s praise safe in his pocket, Tyrone’s momento of greatness reminds him of a life that is long gone. O’Neill highlights the way James moves backward in time overwhelmed by shame so that by midnight, Tyrone has once again become a slave to his regrets. O’Neill uses Tyrone to show the power regret holds over the individual’s ability to move forward. O’Neill describes Jamie, saying, “Jamie, the elder is thirty-three. He has his father’s broad shouldered, deep chested physique, is an inch taller and weighs less, but appears shorter and stouter because he lack’s Tyrone’s bearing and graceful carriage.” O’Neill spends the least time discussing Jamie, but the young man is both perceptive and bitter. Jamie was a well-behaved child with “glowing reports” in his boarding school. After turning to alcohol, Jamie was expelled from boarding school and lost his parents’ favor. Jamie’s interactions with his parents are only criticisms for the thirty-three-year-old son living at home while he watches his parents adore Edmund. Jamie reveals how much his parents’ favoritism of Edmund hurts him in reciting Rossetti, saying, ‘My name is Might-Have-Been; I am also called No More, Too Late, Farewell.’ Mary and Tyrone have given up on his future, leaving Jamie to turn to alcohol and prostitutes to escape the reality of being a disappointment.
Jamie’s character is unclear because he seems to have an equal desire to prove his parents wrong and destroy all joy around him. The ambiguity in Jamie’s character has led to Mary blaming Jamie for murdering Eugene. At just seven years old, Jamie’s measles ended his brother’s life and his mother’s sanity. O’Neill has created Jamie to be the most sorrowful character in the play because he’s the only person no one loves anymore. Jamie knows that he has destroyed his opportunities leaving him to watch the rest of his family crash into personal sadness around him. He is left now to watch his perfect brother be destroyed by his illness. Nevertheless, he is still jealous of Edmund even though Edmund is dying of tuberculosis. Jamie makes a jealous confession to Edmund yelling that Edmund is Mary’s favorite. Readers see the impact of favoritism on Jamie’s view of Edmund. In a drunken state, Jamie reveals that he has always held a grudge against Edmund and he introduced Edmund to alcohol to destroy him. This painful confession is another way O’Neill displays resentment moving individuals backward through time.
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