10 Real People That Inspired Characters on “The Wire”
Criminal Justice Degrees Guide
Jay Landsman (inspiration for Jay Landsman)
The burly Jay Landsman viewers know was inspired by the real-life Landsman, who’s much smaller but no less a character than his fictional counterpart. The real-world Landsman was a homicide detective whom Simon first met when he was researching his book Homicide: A Year on the Killing Streets. (The book would go on to inspire the NBC series.) In one of the many instances in which actual citizens got screen time on the show, the real Landsman became a regular cast member when he took on the role of Major Dennis Mello in seasons three through five.

Possum (inspiration for Bubbles)
Bubbles’ slow-burning story of redemption is one of the most moving arcs of the entire series. He’s one of the most entertaining and likable people on the show, and he was inspired by a real-world police informant who went by the street name of "Possum." Simon met Possum twice before the man died of AIDS; at his family’s request, his true identity remains a secret. He was known for having a good memory and for helping cops identify players in the drug game, traits that would come to define Bubbles from the beginning.

Shorty Boyd, Donnie Andrews, Ferdinand Harvin, Billy Outlaw and Anthony Hollie (inspiration for Omar Little)
The amazing thing about Omar — or one of them, anyway — is how likable he is even while he’s going about his chosen business of killing and robbing people. He’s cavalier about making a living by taking money and stock from drug dealers ("How does a man rob drug dealers for eight or nine years and live to tell about it?" "Day at a time, I suppose."), but his habits and traits were drawn from a variety of real-life stick-up men. Simon based the character on Shorty Boyd, Donnie Andrews, Ferdinand Harvin, Billy Outlaw, and Anthony Hollie, a quartet of stick-up men who worked the Baltimore area between the 1980s and the early part of the 2000s. Andrews, who had since reformed, played a bit part as one of the men who helps protect Omar when he is sent to prison. Andrews died in December 2012.

Rick Requer (inspiration for Bunk Moreland)
William "Bunk" Moreland, known for his pinstriped, lawyerly affectations, was based on BPD detective Oscar "Rick" Requer, also nicknamed Bunk. He worked under Jay Landsman when Simon was researching Homicide, and his demeanor and handle would form the basis for the Bunk, a fan favorite. In another nod to the real man, the series featured a cop named Oscar Requer in its final season.

Timmirror Stanfield (inspiration for Marlo Stanfield)
Marlo Stanfield is a cold-hearted killer and businessman. His name and habits came from Timmirror Stanfield, a Baltimore drug kingpin in the 1980s whose 50-member gang controlled large sections of West Baltimore and committed a string of murders in their quest to maintain power. The investigation led to convictions for many main players in the gang.

Vernon Collins (inspiration for Wee-Bey Brice)
The fish-loving and loyal soldier character of Wee-Bey Brice found real-life inspiration in a man named Vernon Collins. Ed Burns, a co-creator and writer on "The Wire," was a Baltimore detective who investigated a variety of high-profile heroin dealers in the 1980s. One of these, Thomas Taylor, was partnered with Collins, who was known as Bey-Brother. Collins, a feared contract killer, also appeared in Homicide. The real-world Bey was caught in 1987 and sentenced to 35 years behind bars.

Ed Burns (inspiration for Roland Pryzbylewski)
Roland "Prez" Pryzbylewski was behind some of the most heartbreaking moments on "The Wire," from his police mishaps to his time as a teacher. Events from the character’s disparate careers are drawn from the life of Ed Burns, a former detective and the series’ co-creator. Prez’s skill with cracking codes in the Barksdale investigation paralleled Burns’ investigation of a drug dealer named Melvin Williams (whom we’ll get to shortly), and his experiences as a public-school teacher are modeled on those of Burns, who became an educator after leaving the force.
Melvin Williams (inspiration for Avon Barksdale)
Although Simon has said that no one person was the direct inspiration for Avon Barksdale, the drug kingpin at the center of the first season, it’s likely that Avon was drawn from the life and times of Melvin Williams, a drug dealer previously investigated by Burns. Williams was a huge heroin trafficker in the 1970s and 1980s, much like Barksdale, with a similarly violent and unpredictable persona. In an ironic twist, Williams, now out of prison, played a church deacon in later seasons of the show.

Stringer Reed, Roland Bell, Kenneth A. Jackson (inspiration for Stringer Bell)
A number of men went into creating the brilliant but doomed Stringer Bell. His name itself is a combination of Stringer Reed and Roland Bell, a pair of Baltimore drug dealers. But his character also bears a striking resemblance to Kenneth A. Jackson, a Baltimore drug dealer who began to diversify and get into legitimate businesses, including a shoe store, a small market, and an adult entertainment club. Jackson took classes at Baltimore Community College, just like Stringer, to learn more about business and become a full-fledged member of legit society.

Dennis Wise (inspiration for Dennis "Cutty" Wise)
Cutty Wise shows up in the series’ third season, fresh out of prison and already too old for the drug game that’s passed him by while he was away. The real Dennis Wise was a contract killer in 1970s Baltimore who was connected to Vernon Collins and who consistently eluded police efforts to capture and convict him. He eventually went to prison but used his time there to get a bachelor’s degree and write a novel. The fictional Cutty makes smarter choices, opting to leave the game and open up a gym for local kids. I like that version better.
Write the lyrics for a misc song made in 2014, titled "10 Real People That Inspired Characters on “The Wire”", by artist "Criminal Justice Degrees Guide".