Lil Zay Osama Enters “Not Guilty” Plea In Machine Gun Case

Lil Zay Osama is in a tough spot. The Chicago rapper entered a plea deal after being caught with a machine gun and unregistered firearm in September 2022. He was indicted on weapon charges in January, and has decided to plead not guilty. According to AllHipHop, Lil Zay Osama was detained following his plea, and will be due back in court on May 21.

The prosecution claimed that Lil Zay Osama, real name Isaiah Dukes, brought a Glock pistol with him to New York. He allegedly left the weapon in a rideshare vehicle that took him from a Manhattan hotel to a Queens recording studio. Breon Peace, the U.S. Attorney for the Eastern District of New York, issued a statement denouncing the rapper’s actions. “This office, together with our law enforcement partners, will continue to work diligently to protect our communities from such dangerous weapons,” he wrote. “Machine guns have no place on the streets of our communities.”

Read More: Lil Zay Osama Arrested After Leaving Gun In An Uber: Report

Lil Zay Osama Faces Up To 20 Years In Prison

Lil Zay Osama
ATLANTA, GA – NOVEMBER 27: Lil Zay Osama backstage during G Herbo In Concert at Tabernacle on November 27, 2021 in Atlanta, Georgia.(Photo by Prince Williams/Wireimage)

His legal troubles in New York have not stopped him from getting into trouble in his native Chicago. The rapper was arrested with two other men following a high-speed chase in December 2023. He was charged with the theft of stolen goods that were valued between $10,000 and $100,000, and the possession of a loaded machine gun. Both are considered felonies. Lil Zay Osama hopped on Instagram Stories following the arrest to assure fans that he would be fine. “I guarantee n****s gone need me before I need them,” he stated. “I’ll be home sooner than you think.”

The rapper may have been correct in the short term, but he’s facing a long prison sentence in New York. The 26-year-old is looking at 20 years in prison if convicted on all charges. His music career has drastically slowed down in the wake of these charges. He dropped his last mixtape, 4 the Trenches, in August 2023, and his last single “I Made It”, was released the same month he was arrested in Chicago. Time will tell if the single was a premature celebration or a promise of brighter days to come.

Read More: Lil Zay Osama Arrested For Gun Possession & Robbery: Report

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112’s ‘Cupid’ Video Gets Some ‘React Like You Know’ Love From 2Rare And TiaCorine

Our React Like You Know series is a hit. In the last episode, we quizzed today’s generation of rappers on the hip-hop cult classic track “Get Money” by Junior Mafia featuring The Notorious B.I.G. and Lil Kim. Now, we’re testing a range of Gen-Z recording artists on their knowledge of ’90s R&B, starting with 112’s 1997 song, “Cupid.”

Up to put their musical wits to the test are 2Rare, TiaCorine, Lil Zay Osama, TraTwoThree, Kalan.FrFr, Nascar Aloe, Raiche, Kyle Banks, Bolsen, Pheelz, and more. While many had a laugh about the video’s dated look, comparing it to a 90s Black Harry Potter film, they unanimously agree that the platinum plaque hold record is undeniably smooth.

Rapper 2Rare’s look for the song went a step further as he sampled the song on his breakout single, “Q-Pid” featuring Lil Durk. You can watch his performance of the record as part of our UPROXX Sessions here.

When asked about what about the song made him want to sample it, 2Rare replied, “I’ve been wanted to sample it. I’ve always loved the song. So, when I heard the sample [from DJ Smalls 732], I was like, ‘Yeah, that’s the one,’” he added. “It’s a great song. It’s one of those ones. It makes you feel good.”

You can watch our panel react to the “Get Money” video above.

Some artists covered here are Warner Music artists. Uproxx is an independent subsidiary of Warner Music Group.

Lil Zay Osama Reportedly Arrested, Firearms Seized

While details remain scarce, new reports state Lil Zay Osama has been arrested in his hometown. Information about the Chicago rapper’s alleged arrest first circulated following Tom Ahern’s tweets. The Deputy Director of News Affair and Communications for the Chicago Police Department shared several images of firearms seized during an investigation.

“Illinois State Police @ChicagoIsp identified a stolen vehicle with multiple occupants who fled into a building,” Ahern stated. “ISP has a person of interest in custody at this time. Firearms were recovered. Investigation continues.”

Read More: Lil Zay Osama Calls For Help From Jay-Z & Kim Kardashian After Arrest

Ahern further added, “[Three] of 4 offenders have been taken into custody. 6 firearms were recovered. @Area3Detectives are investigating.”

Later, a Chicago PD Scanner account added more context, alleging that Osama was one of the people detained.

“One of the offenders in custody is reportedly Chicago rapper Isaiah Dukes, better known as Lil Zay Osama,” the tweet read. “He has a net worth of approx $600k. Dukes is a member of Bad Side Cali 6300 gang, a mix of Black P Stones, Gangster Disciples & Black Disciples.

It also shared, “He signed to Warner Records.”

Read More: Lil Zay Osama Arrested After Leaving Gun In An Uber: Report

In September 2022, Lil Zay Osama was arrested in New York after reportedly leaving a firearm in an Uber. The rapper was on Livestream when it occurred, and later, he called on Jay-Z and Kim Kardashian to help him with his case.

Additionally, Osama reportedly posted $350K bail and was released. He has not yet confirmed or denied reports of this most recent arrest.

ATLANTA, GA – NOVEMBER 27: Lil Zay Osama backstage during G Herbo In Concert at Tabernacle on November 27, 2021 in Atlanta, Georgia.(Photo by Prince Williams/Wireimage)

Lil Zay Osama Arrested On Gun Charges In Chicago

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According to several confirmed reports, Isaiah Dukes aka Lil Zay Osama is back behind bars on illegal weapons charges in Chicago.

Details are scarce about the most recent arrest, but it is being reported that Chicago Police found several illegal weapons in the vehicle of the 25-year-old CHi-Town native, including two assault-style rifles and multiple handguns. 

Lil Zay Osama is best known for his Trench Baby series, which includes his “Fuck My Cousin” singles, featuring Lil Durk on the second version.

TheSource.com will update this story as details develop.

The post Lil Zay Osama Arrested On Gun Charges In Chicago appeared first on The Source.

Lil Zay Osama Brings The Melodic ‘Mmmhmmmm’ To ‘UPROXX Sessions’

Lil Zay Osama started rapping when he was just eight years old, and over 15 years later, he’s a Southside Chicago favorite with a feature from Lil Durk on his most recent project. His debut album, 2019’s Hood Bible, put him on the map for departing from his city’s infamous drill sound, featuring more pop-leaning records like “Percocet Crazy.” Combined with a dedicated fanbase and viral YouTube videos under his belt, Lil Zay Osama isn’t a Chicago newcomer anymore. He’s here to stay.

Today, the Chi’s Lil Zay Osama brings his “pain music” to the bathroom stage with his single “Mmmhmmmm.” The track comes from his most recent mixtape, Trench Baby 3, which also featured the hit “F*ck My Cousin.” His performance is melodic but doesn’t compromise the grittiness of his hometown’s sound. The track’s chorus is inspirational and candid as Lil Zay raps about his successes and gives insight into his rules of the streets.

Watch Lil Zay Osama perform “Mmmhmmmm” for UPROXX Sessions above.

UPROXX Sessions is Uproxx’s performance show featuring the hottest up-and-coming acts you should keep an eye on. Featuring creative direction from LA promotion collective, Ham On Everything, and taking place on our “bathroom” set designed and painted by Julian Gross, UPROXX Sessions is a showcase of some of our favorite performers, who just might soon be yours, too.

Lil Zay Osama is a Warner Music artist. Uproxx is an independent subsidiary of Warner Music Group.

Lil Tjay Lends A Melodic Hand To Lil Zay Osama’s Free-Spirited Video For ‘Emotions’

After showing off his potential on his 2019 major-label debut album, True 2 Myself, Lil Tjay returned with his follow-up Destined 2 Win earlier this year. The project saw the Brooklyn native flaunting more of his artistry and skills across the 21 songs. A little more than a month removed from that album’s arrival, Tjay lends his talents to rising Chicago rapper Lil Zay Osama in a video for their nonchalant collaboration “Emotions.” In it, the duo surrounds themselves with a cast of women during a video shoot while detailing their displeasures towards emotional people.

The song can be found on Lil Zay Osama’s most recent project, Trench Baby, which he released in February with features from Jackboy, G Herbo, Doe Boy. Earlier this month, he dropped a deluxe re-issue of the album with four new tracks and additional appearances from Stunna 4 Vegas, Sada Baby, and Sheff G.

The new video comes after Lil Tjay earned his highest-charting single thanks to “Calling My Phone,” featuring 6lack, which peaked at No. 3 on the Billboard Hot 100. Recently, he also shared videos for “Love Hurts” and “Oh Well,” both also from the Destined 2 Win album.

You can watch the “Emotions” video above.

Trench Baby (Deluxe) is out now via Warner. Get it here.

Some artists covered here are Warner Music artists. Uproxx is an independent subsidiary of Warner Music Group.

2021 XXL Freshman Class 10th Spot – Vote Now

Before the annual Freshman Class cover is revealed, it’s time to cast your vote for the 10th spot. Continue reading…