The first thing we notice about James is that he's actually pretty adorable. He's naïve and sentimental, but he's also charmingly misanthropic and very temperamental. James is really like a big old twelve-year-old: grumpy and quick to fight, but a teddy bear on the inside.
James's first instinct is to argue, like when Jamie pokes fun at his snoring and James snaps back: "If it takes my snoring to make you remember Shakespeare instead of the dope sheet on ponies!" (1.1.40) Still, he's quick to settle down again when his wife Mary tells him not to be so "touchy," and he's downright after-school special when he talks about his dear old mother, wiping tears from his eyes: "A fine, brave, sweet woman. There never was a braver or finer" (4.1.135).
But this fighting instinct can be a major problem. Check out Jamie's "Character Analysis" for more on this, but James is constantly jumping down his elder son's throat, accusing him of being disrespectful and lazy. If you can find a passage in the play in which both Jamie and James are present, it's almost a guarantee that they're fighting.
Now, James may be correct in thinking that his eldest son is disrespectful and unmotivated. Still, James seems to lack the maturity to give the clearly troubled Jamie even one compliment or supportive comment. Instead of being the responsible parent in the room, James always usually gets angry. Of course, James's father ditched his family when he was ten, so he hasn't exactly had great role models for fatherhood. He had to grow up too young. Since he never went through the normal child development process, it's easy to imagine why he might still have some childish qualities.
The word "whiskey" comes from the Gaelic for "water of life." James would seem to agree with his Irish ancestors. He admits that he used to give whiskey to his sons as medicine when they were children. We even see him give it to Edmund as a tonic for his tuberculosis. Indeed he's so fond of the stuff that it's one of the very few things on which he'll actually spend money.
Despite the fact that James, like his sons, drinks all day long, he refuses to admit that he has any sort of problem. Mary would disagree. She brings up the fact that once his actor friends had to carry him drunk up the stairs – this was on their honeymoon. James flatly denies it, but stage directions tell us he seems very guilty. We've got a pretty good idea he's lying. James's biggest defense against any accusation of alcoholism is that he's never missed a performance (he's an actor). While this may be true, it doesn't prove that James doesn't have a dependency problem.
It would seem that James uses this "water of life" to avoid life all together. At the beginning of Act IV we find James alone and drunk with two bottles of whiskey. O'Neill tells us in his stage directions "despite all the whiskey in him, he has not escaped" (4.1.1 SD). He has a lot that a person might want to hide from: Edmund may be dying, Jamie loathes him, and his wife is addicted to morphine. To make matters worse, he's partly to blame for it all.
Yes, it seems like we've found another cycle in this play of cycles. Just like his wife, James seeks to hide from his problems in a cycle of drug abuse. We can see why O'Neill describes him as "a sad, defeated old man, possessed by hopeless resignation" (4.1.1 SD).
What evidence is there that James is a miser? Oh, where to begin? There's the low wages James insists on paying his chauffeur, who makes up for his bad pay by cheating the family on car repair bills. There's the shabby house, in which "everything [is] done in the cheapest way" (1.1.94). James is too miserly to even turn on the lights at night.
James's practice of skimping on medical bills is probably the most damning. He insists on using cheap doctors like Dr. Hardy and the hotel doctor that got Mary hooked on morphine. To top it all off, James wants to repeat the mistake of cheap medical care by sending Edmund to a low-grade sanatorium.
Besides whiskey, the only thing James likes to spend money on is real estate investments. The depth of his obsession with land is revealed when he buys a piece of property right after agreeing to the junky sanatorium for Edmund. His real estate investments are really just another symptom of his miserliness. He thinks that buying land is a lot safer than keeping it in banks or in the stock market. Well, he may have a point there (though he doesn't know it, the Great Depression is right around the corner). The problem is that by throwing all his money into land, he doesn't leave enough cash around to give his family the life they deserve.
Of course, James's miserliness has its roots in the past. James was born in Ireland, but when he was nine years old, his father uprooted the family and moved to the United States for a new start. Sounds great. But then, a year later, James's father abandoned the family, returned to Ireland, and committed suicide. James's older brothers had already left, so this disaster left James the head of the household – as a ten-year-old. He was forced to work in a machine shop making files. When Edmund hears this sad story he feels pity for his father and doesn't blame him quite so much. We can kind of see why James is so concerned about money.
Ultimately, James's obsession with money has done him the most harm. He had a promising career as a Shakespearian actor. He was living the American dream. He'd pulled himself up out of poverty and made it in a big way. He quickly became a rising star on Broadway, even receiving praise from Edwin Booth, the most famous actor of his day. James was so honored that he wrote out the exact words Booth used, and "[read] it every once in a while until finally it [made him] feel so bad [he didn't] want to face it anymore" (4.1.145). For more on the symbolism of James's piece of paper, head on over to "Symbols, Imagery, Allegory."
James's miserliness turns out to be the undoing of his promising acting career. James took the star role in an extremely successful play, but instead of moving on and further developing his talents, he stayed to keep raking in the bucks. By the time he wanted to get out of this show, he'd lost his ability to take on more challenging roles. James admits that he did this for the money. It's one of the great sorrows of his life. He says to Edmund, "What the hell was it I wanted to buy, I wonder, that was worth – well, no matter. It's a late day for regrets" (4.1.139).
Just like the rest of his family, James almost seems to move backward in time over the course of the play. It's not until Act IV that we get the full big sad story of his impoverished childhood and soul-sucking acting career. He doesn't become as completely consumed by memory as Mary, but still by the time midnight roles around his old regrets have him firmly in their clutches. As we mention in "What's Up with the Ending?", James's backwards journey echoes the structure of the entire play.James Tyrone Timeline