Omar Devon Little is a feared and notorious stick-up man, frequently robbing street-level drug dealers. Omar's unique characteristics include a personal morality code (refraining from harming those not in "the game"); Omar's homosexuality and privately tender nature; his refusal to use profanity (which sets him apart from most street-level players); his scar, probably from a blade, from his right cheek to his central brow; his use of a short 12-guage shotgun; and his haunting whistle of the tune, "The Farmer in the Dell," as an ominous warning to the neighborhood that Omar has something on his mind. Often that is his inevitable conflict with the Barksdale and Stanfield drug organisations, because of his drug/money robberies. Some of these raids, no matter how well-planned, do not go well. Omar Little seems to have an uncanny knack for survival in these situations, avoiding hails of bullets, knowing when to escape, knowing when it is not worth it to simply reach over and grab valuables before he runs. Omar is also noted for his close relationships with his partners, and with his guardian and ad hoc banker Butchie. Butchie's execution was enough to motivate Omar from a peaceful tropical retirement to an impulsive revenge mission.
Omar was orphaned at a young age, and raised by his grandmother Josephine, who is largely responsible for his strict moral code. He attended Edmondson High School in West Baltimore. For more than ten years, Omar has made his living holding up drug dealers, and staying alive "one day at a time". He is legendary around Baltimore for his characteristic shotgun, trench coat, facial scar, and whistling the "The Farmer in the Dell". He repeatedly demonstrates exceptional skill as both a stick-up man and shooter, further contributing to his feared status as an efficient professional. Once a month, he accompanies his elderly grandmother to church. He also has a brother, alluded to a few times in the series, named "No Heart" Anthony, incarcerated since the early '90s for a jewelry store robbery.
After Omar, his boyfriend, Brandon Wright, and John Bailey robbed a stash house, Avon Barksdale put out a contract on the trio. Bailey was killed, and Brandon was tortured, mutilated, and killed for keeping silent on Omar's whereabouts. In response, Omar cooperated with Detectives Jimmy McNulty and Bunk Moreland, providing key information leading to the arrest of Barksdale soldier Bird, and agreed to be a witness against him at his trial (though he was not an actual witness to the crime). While meeting with the police, he observed information which he used to exact further revenge against the Barksdale Organization, killing Stinkum and wounding Wee-Bey Brice.
Omar even got a shot at Barksdale himself, by giving stolen drugs to Eastside drug kingpin Proposition Joe for Avon's pager number. He tailed Avon to Orlando's strip club, paged him and waited for him to emerge into the open. Avon narrowly escaped when Wee-Bey arrived and shot Omar in the shoulder. Afterward, Stringer Bell offered Omar a truce, planning to kill him when he relaxed his guard. Omar realized Stringer's duplicity and left town, temporarily relocating to New York City.
Omar returned to Baltimore with a new boyfriend, Dante, sometime between the seasons. He quickly returned to his old business, targeting the Barksdales exclusively, and connected with Tosha and Kimmy, stick-up artists who joined his crew.
Omar provided false testimony against Bird in open court as he had promised to do. Unabashed and unapologetic about who he was, he won over the jury with his wit; when Barksdale attorney Maurice Levy called him a parasite who thrived on the drug trade, Omar quickly pointed out that a crooked lawyer like Levy was essentially the same thing. In the end, the jury accepted Omar's testimony, and Bird was sent to prison for life. Assistant State's Attorney Ilene Nathan promised Omar a favor as a thank you for his testimony.
Around this time, Stringer Bell wanted to get rid of hitman Brother Mouzone. At a meeting arranged through Proposition Joe and Omar's advisor and confidant Butchie, Stringer told Omar that Mouzone was the one who tortured and murdered Brandon. Omar then tracked Mouzone down at a hotel and shot him in the abdomen. In the brief conversation that followed, Mouzone convinced Omar that they both shared the same type of moral code. Omar, realizing he had been duped, let Mouzone live, even calling 911 and giving them Mouzone's location. He redirected his murderous intent at Stringer himself.
During a raid on a Barksdale house, Tosha was accidentally killed by Dante in the middle of a fire fight, and Omar contemplated giving up his war against the Barksdale organization. Detective Bunk Moreland, investigating the deaths, made Omar feel further guilt over the incident, and Omar provided him a lost police pistol as a way of making amends.
Under orders from Stringer Bell, two of Avon's soldiers attacked Omar while taking his grandmother to church. Omar forced her into a taxi, but she lost her best hat in the gunfire. This blatant violation of the longstanding "Sunday truce" between rival gangs led Omar to re-dedicate himself to war with the Barksdales, though Kimmy opted out. Avon, outraged at Stringer, ordered the men responsible for the attack to buy Omar's grandmother a new hat.
Meanwhile Brother Mouzone captured Dante, and forced him to reveal Omar's hiding place. (Dante gave in almost immediately, in contrast with Brandon who never cracked.) Mouzone suggested an alliance against Stringer. Together, Omar and Mouzone ambushed Stringer during a meeting with a property developer and executed him. Brother Mouzone set Dante free and returned to New York, and Omar threw his shotgun and Brother Mouzone's pistol into the harbor. Bunk Moreland managed to get assigned to this murder as well.
Omar felt dissatisfied with how easy work had become and worried that pursuing easy thefts would make him soft, so he and new boyfriend Renaldo pull a robbery of one of Marlo Stanfield's dealers, Old Face Andre who ran a westside corner store that was in actuality a drug front. At Proposition Joe's suggestion, they proceeded to rob a card game, not knowing that it was held by Marlo Stanfield; Marlo vowed to get revenge. Chris Partlow framed Omar for the murder of an innocent woman at Old Face Andre's convenience store, and Omar was jailed. During the arrest, he is initially robbed by Officer Walker and questioned by Officer Jimmy McNulty who is puzzled as to why a murder warrant is present for Omar murdering a citizen. When imprisoned in Baltimore City's Central Booking, Omar recognized many of the inmates as people he'd robbed previously and correctly surmised they may try to kill him. In retaliation for an attempt on his life, he brutally stabbed his attacker in the rectum as a means of warning the other inmates not to attack him.
Omar was able to convince Detective Bunk Moreland that he would never kill a "citizen". After having Omar transferred to a safer prison (calling in the favor from Ilene Nathan), Bunk managed to prove Old Face Andre's lies. The charge against Omar was dropped and Bunk transported him out of Harford County with a warning - no more murders of anyone. The unsolved murders at his hands that Bunk knows about, such as Stringer Bell or Tosha, will be brought up if Omar is caught killing anyone else.
Omar found out that Marlo framed him, and was the one he robbed at the card game. Omar demanded that Proposition Joe help him rob Marlo, and Joe agrees to alert Omar when Cheese is dropping off Marlo's package. Omar orchestrates an elaborate and successful hijacking of Joe's entire shipment of heroin as it enters port. As he had no wish to sell drugs on the street, he sold the heroin back to Proposition Joe. As of the end of the season, he has made a lot of money, but has all of the dealers ready to put a contract on his head.
Omar retires with Renaldo following the heist and moves to San Juan, Puerto Rico. Marlo Stanfield has Butchie tortured and killed, seeking revenge on Omar. Word reaches Omar and he returns to Baltimore to punish those responsible. Omar ambushes Slim Charles and confronts him. Omar knows that Slim Charles' employer Proposition Joe knew of his connection to Butchie and believes Stewart may have been responsible. Slim Charles is able to convince Omar of Stewart's innocence and Omar targets Stanfield. Along with Butchie's friend Donnie, Omar decides to go after Stanfield's people as Stanfield himself has gone into hiding and Omar targets Monk. Stanfield's soldiers spot Omar outside of Monk's apartment and bait Omar and Donnie into an ambush. Once inside they are attacked by Chris Partlow, Snoop, Michael Lee, and O-Dog. During the shootout, O-Dog is wounded in the leg and Donnie killed by a gunshot to the head. Out of bullets, Omar is forced to jump from the fourth-story balcony, severely injuring his leg in the process.
After hiding out in the basement of Monk's building and tending to his injured leg (it isn't revealed if he actually broke it), Omar continues his mission, going on a "warpath" around the city in search of Marlo, limping with a makeshift crutch. He terrorizes and robs many of Marlo's corners and shoots or kills several members of Stanfield's crew including Savino Bratton. Omar constantly calls for Marlo to meet him on the streets, leaving the message with Marlo's corner and stash house crews. During "Clarifications", a young boy from Michael's crew, Kenard, follows Omar to a Korean-owned convenience store. Omar sees Kenard walk in and gives him a sidelong glance, but seeing just a little boy, pays no attention to him. Kenard shoots Omar in the side of the head, killing him. This brings closure to some of the foreshadowing in Season 3, as Kenard was the young boy Bunk witnessed imitating Omar at the Barksdale stash house shootout. His death has several parallels with that of Errol Barnes in writer Richard Price's Clockers.
News of Omar's death are received with mild amusement and indifference by various characters. Bunk Moreland initially shows some sympathy, which he brushes aside when he learns Omar was once again "on the hunt". McNulty and Freamon react with mere curious interest and instead focus on a lead on their case found on Omar's body. The newspaper staff drop any mention of the incident for lack of printing space. In his final appearance, an employee at the morgue realizes the identification tag on Omar's body has been accidentally switched with that of the white deceased male on the neighbouring table and corrects the error by swapping the tags. The scenes signal the unceremonious transition of Omar from a mythical figure into a crime statistic in the course of one day. However, various people in the street were shown to incorrectly exaggerate the details of his shooting in order to glorify his death.
A brief prequel released before season five and on the season five DVD set features a young Omar, his brother Anthony, and an unidentified older boy planning and executing a robbery of a man at a bus stop in 1985 Baltimore. Even as a young boy Omar shows remarkable intelligence, morality and force of character by first questioning the value of robbing the man and then compelling the unidentified older boy (at gunpoint) to return the money. Anthony expresses tired amusement at Omar's actions, demonstrating his familiarity with his brother's forceful personality. Omar is shown with his characteristic facial scar, indicating that he somehow received it as a child.
At the end of this segment, the unidentified boy tells Anthony that his brother is not "cut out" for their line of work, an ironic foreshadowing of what would happen to Anthony some years later. After bungling a jewelry store heist, Anthony was pursued by police. Apparently sensing he was about to be caught, and unwilling to do hard time, Anthony put a gun to his chest and pulled the trigger. He survives the suicide attempt, however; only receiving a contact wound. After this incident, he earned the derisive nickname "No Heart" Anthony.
- Anton "Stinkum" Artis: Shot once in the chest from shotgun bullets as revenge for Brandon.
- Stringer's Bodyguard: Shot once in the chest from shotgun bullets.
- Russell "Stringer" Bell: Shot to death by Omar and Brother Mouzone for setting both of them up to get murdered.
- Manny: Shot to death off-screen.
- Savino Bratton: Shot once in the head for being a past Barksdale enforcer and to lure Marlo onto the streets.
|Season 1 appearances|
|"The Target"||"The Detail"||"The Buys"||"Old Cases"||"The Pager"|
|"The Wire"||"One Arrest"||"Lessons"||"Game Day"||"The Cost"|
|"The Hunt"||"Cleaning Up"||"Sentencing"|
|Season 2 appearances|
|"Ebb Tide"||"Collateral Damage"||"Hot Shots"||"Hard Cases"||"Undertow"|
|"All Prologue"||"Backwash"||"Duck and Cover"||"Stray Rounds"||"Storm Warnings"|
|"Bad Dreams"||"Port in a Storm"|
|Season 3 appearances|
|"Time after Time"||"All Due Respect"||"Dead Soldiers"||"Amsterdam"||"Straight and True"|
|"Homecoming"||"Back Burners"||"Moral Midgetry"||"Slapstick"||"Reformation"|
|"Middle Ground"||"Mission Accomplished"|
|Season 4 appearances|
|"Boys of Summer"||"Soft Eyes"||"Home Rooms"||"Refugees"||"Alliances"|
|"Margin of Error"||"Unto Others"||"Corner Boys"||"Know Your Place"||"Misgivings"|
|"A New Day"||"That's Got His Own"||"Final Grades"|
|Season 5 appearances|
|"More with Less"||"Unconfirmed Reports"||"Not for Attribution"||"Transitions"||"React Quotes"|
|"The Dickensian Aspect"||"Took"||"Clarifications"||"Late Editions"||"–30–"|
Michael K. Williams received the part after only a single audition, although the character was initially slated to appear in just seven episodes before dying. Williams has stated that he pursued the role because he felt it would make him stand out from other African Americans from Brooklyn with acting talent because of its contradictory nature.
David Simon has said that Omar is based on Shorty Boyd, Donnie Andrews, Ferdinand Harvin, and Anthony Hollie, Baltimore stickup between the 1980s and early 2000s who robbed drug dealers. Donnie Andrews later reformed, is married, and now helps troubled youth. 
For his portrayal of Omar, Michael K. Williams was named by USA Today as one of ten reasons they still love television. The character was praised for his uniqueness in the stale landscape of TV crime dramas and for the wit and humor that Williams brings to the portrayal. Omar has been named as one of the first season's richest characters, not unlike the Robin Hood of Baltimore's west side projects, although his contradictory nature was questioned as a little too strange. The Baltimore City Paper named the character one of their top ten reasons not to cancel the show and called him "arguably the show’s single greatest achievement."
Williams has stated that he feels that the character is well liked because of his honesty, lack of materialism, individuality and his adherence to his strict code.
- ↑ Character profile - Omar. HBO (2004). Retrieved on 2006-07-21.
- ↑ Dan Kois (2004). Everything you were afraid to ask about "The Wire". Salon.com. Retrieved on 2006-07-12.
- ↑ Bunk Chides Omar. You Tube (2004). Retrieved on 2006-08-09.
- ↑ 4.0 4.1 "Transitions". Dan Attias, Writ. Ed Burns (story and teleplay), David Simon (story). The Wire. HBO. 2008-01-27. No. 4, season 5.
- ↑ 5.0 5.1 Joel Murphy (2005). One on one with... Michael K. Williams. Hobo Trashcan. Retrieved on 2006-07-21.
- ↑ Richard Vine (2005). Totally Wired. The Guardian Unlimited. Retrieved on 2006-07-19.
- ↑ Urbina, Ian. "From Two Broken Lives to One New Beginning", The New York Times, 2007-08-09. Retrieved on 2007-08-11.
- ↑ Robert Bianco (2004). 10 Reasons we still love TV. USA Today. Retrieved on 2006-07-21.
- ↑ Chris Barsanti (2004). The Wire - The Complete First Season. Slant Magazine. Retrieved on 2006-07-20.
- ↑ Brent McCabe and Van Smith (2005). Down to the wire: Top 10 reasons not to cancel the wire.. Baltimore city paper.. Retrieved on 2006-07-21.