Step 1) Stop reading immediately (though you probably would do this anyway). There are spoilers below, and I will not be held responsible for ruining the greatest show of all time.
Step 2) Watch the entire series on HBO Go. If you do not get HBO, this is a fixable problem.
Step 3) Come back and read all of the character reviews I've completed so far. If you enjoy good TV, you will binge all 60 episodes and finish the show before I finish the character rankings.
Step 4) Find a new job. In retrospect, that was a bad decision watching a full season of The Wire every day for five days because your employer expected you to show up to work. You need a means to pay for HBO so that you can watch all the episodes again.
Previous Installments
Characters #20 - #16
Characters #25 - #21
Characters #30 - #26
15) Michael Lee
Like some other kids on the show, Michael's home life is a disaster. His mother is a lazy drug addict and his little brother's father is sexually abusive. As a result, Michael is often in his own world, greatly distrustful of others and quietly refusing to do things. One such refusal involved an offer of no-strings-attached cash from Marlo Stanfield, which got the attention of Marlo and his lieutenants.
While the general aloofness makes sense, it makes it initially tougher to warm up to Michael as a character. Throughout Season Four, though, Michael gives us plenty of reason to like him, He's basically a father to his brother, Bug, and fiercely fights people that pick on his friends. Unfortunately, Michael slips away from his friends in the later parts of the season, as he turns to the Stanfield crew for help with getting rid of Bug's father. He eventually becomes one of Marlo's lieutenants and a stone cold killer, carrying nothing with him from his past life besides Dukie and Bug.
Throughout much of Season Five, Michael questions a lot of the violence carried out by Marlo and his crew, as it often seems needless. He arouses mild suspicion in Marlo, which leads to Snoop attempting to kill him. Michael figures out the plot and turns the tables on Snoop, followed by going into hiding. It's implied in the last episode of the series that he effectively becomes the new Omar. It's pretty fitting.
Greatest Character Moment: Of course, going into hiding means saying good-bye to Dukie, and no scene better exemplifies how Michael has lost any sense of his former self.
14) Randy Wagstaff
The first thing that struck me about Randy was his last name, Wagstaff. It's the same as that of Cheese, and although it's never revealed on the show, the implication (confirmed by Simon) is that Cheese is Randy's dad.
Randy's just such an easy kid to like. He gets himself into trouble sometimes, but it's Bart Simpson trouble and not shoot-'em-up-and-deal-drugs trouble. He runs a crafty candy-selling business at school and is good for creative pranks, but for the most part, Randy is uneasy about anything that breaks serious rules. Unfortunately, he finds himself as a relatively innocent accessory to a murder and an alleged rape. This leads to him divulging more information than many would like to school faculty and police officers, and he winds up getting a reputation as a snitch, in large part thanks to Marlo Stanfield.
Snitches don't fare very well on the streets of Baltimore, and what starts as ridicule and intimidation becomes more violent when gang members destroy his foster home with molotov cocktails, severely incapacitating his foster mother and leaving him with no one to look after him. Sargeant Ellis Carver tries his best to help him but he's ultimately sent back to live at a group home, where his snitch reputation gets him beaten up by older kids. We see Randy one last time in Season Five, refusing to give information to police and becoming one of the very thugs that used to prey on him.
Randy's demise is tough to watch because he came from probably the best living situation of the four kids and the system got to him anyway. Through Randy, we see how a nice, well-meaning kid with some support can still get swallowed up by the streets of Baltimore. You feel like Randy could grow up to be a person who really puts his mind to something constructive and be successful. Instead, that future goes to the less-deserving Namond.
Greatest Character Moment: Carver ultimately fails to protect Randy, and Randy uncharacteristically lashes out at him in a pretty tough scene to watch. Later, in an even tougher scene to stomach, Carver drops him off at the group home and Randy thanks him for his efforts, telling him that he doesn't need to feel bad because he tried his best. It's one last reminder of how awesome Randy is before he's lost forever.
13) Roland "Prez" Pryzbylewski
Prez is introduced to us as a real screw-up of a cop, a guy who makes the wrong, often violent decision when pressed into difficult situations. He pistol-whips a teenager, punches his father-in-law Valchek when the latter berates him in front of his peers, and mistakenly shoots and kills one of his fellow officers when pressed into street duty in Season Three. He proves to be useful and intelligent in his behind-the-scenes work, but it's clear he's not really cut out to be a cop.
After that last horrible mistake, Prez chooses to leave the force and becomes a teacher. He seems to want to do this job for the same reason that most probably do -- it gives you a chance to help kids and come up with your own creative way to help others learn. However, Prez meets unexpected difficulties pretty early in his tenure, and it's far worse than the usual complaints of heavy hours, disinterested children, and being underappreciated. His class is a zoo that he's unable to control, and one student bloodily assaults another with a boxcutter.
Prez eventually gets his students to take an interest in math by teaching it to them in terms of gambling. His creative methods seem to work, but much like the police department, the school's leadership is just interested in statistics (in the form of test scores), and they try to force him to abandon his successful tactics and teach students how to pass a standardized test. Prez resists this and ultimately gains the respect of his students by the end of the year.
During the season, Prez does his best to care for Dukie, whose home situation is terrible, and Randy, who is in danger due to his alleged snitching. Despite Prez's successes, he's able to save neither. One person's efforts can get some positive results in this world, but it's often not enough.
Greatest Character Moment: I can't find it on YouTube! My favorite moment for Prez is in the final episode in Season Four, when one of his students makes a disruptive comment, but the other kids don't laugh. It's a big success for Prez, as he's finally in control. I want to give you something though, so here's Prez delivering his famous "No one wins. One side just loses more slowly" quote.
12) Lester Freamon
The man they call Cool Lester Smooth. He initially appears to be a relatively useless detective, similar to the other old guys Daniels got stuck with in Season One, but Freamon quickly proves his aptitude by engineering multiple key breakthroughs in the Barksdale case. He becomes one of, if not the most respected detectives in what would eventually become the Major Crimes Unit and is largely responsible for cracking the biggest mysteries in four of the five seasons of the show.
Freamon is referred to by Bunk as "natural po-lice" very early in the show's run and there really couldn't be a better description of him. It seemed that his long tenure in the pawn shop unit really killed his love of his job, but once given an opportunity to do real work again, the passion came back and he's consistently the most dedicated and focused detective we spend time with. He's typically the voice of reason in the detail and is strong as a leader; my favorite example of this is when he rallied the detectives to do their important work in the wake of Kima getting shot.
Not too bad for the old hump that sits around making dollhouse furniture.
Greatest Character Moment: Lester clashes with McNulty a good deal in Season Three and I'd like to think that this discussion he has with him is responsible for McNulty switching to a less-stressful patrol position in the western district. The clever shot of the picture of Beadie at the end of the scene somewhat confirms that. For a guy who isn't worth the skin off of Lester's knuckles (junior), Lester sure does a lot to help Jimmy.
11) William 'Bunk' Moreland
Bunk is a witty, intelligent homicide detective and provides a lot of comic relief over the course of the series. He's a veritable quote machine and a man with a moral code (albeit one that includes plenty of drunken infidelity). Bunk typically toes the company line and is well-respected by his superiors, particularly Landsman. There's no underlying message from Simon or anything about Bunk that makes you get all the feels. He's just awesome to watch and entertaining pretty much whenever he's on-screen, partly because Wendell Pierce is fantastic and partly because he's fed some excellent lines by the writers.
Bunk most often shows his true colors in his relationships with Jimmy McNulty and Omar. When McNulty goes over the line in Season Five inventing a fake serial killer to get funding for the police department, Bunk refuses to support him, understanding that there's a limit on the means one should go through to do good police work. He also successfully gets through to Omar about the immorality of his actions, despite Omar's "code" of only attacking people who are wrapped up in 'the game'. Bunk would be the best character on any number of shows, but this is The Wire.
Greatest Character Moment: There's a gigantic laundry list of quotes to choose from, but his best (and most important) scene is his confronting of Omar in Season Three about his ways.
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