Taylor was raised in the Englewood, to a large family. During his formative years growing up in a notorious 16-story high-rise housing projectcalled “Calumet Building”, he became affiliated with the Black Disciples gang early as age five, becoming a member by his preteens after relocating to "64th and Normal" in Englewoodwhere he became close friends with Lil Durk.

Taylor gained recognition when he was featured on Chief Keef's hit "I Don't Like", which garnered widespread international attention. He then began to receive popularity through his music videos, including "Us" and "Beef". He then caught the eye of producer No I.D., who had produced albums or tracks for artists such as Common, Kanye West, and others, which led Taylor to sign with hip hop label Def Jam.^[4]

In November 2012, he released a remix for his song "Us" with Rick Ross and Drake which later appeared on Rick Ross' mixtape The Black Bar Mitzvah.^[5] Taylor also created many songs with up-and-coming music producers, such as Young Chop. He is also featured on Juelz Santana's song "Bodies". In January 2013, Taylor released a remix to his song "Traffic" featuring Young Jeezy and Twista. On September 2, 2013, Taylor released his second solo mixtape Supa Savage, featuring guest appearances from Chief Keef, Lil Durk, Fredo Santana, Wale and Waka Flocka Flame.^[6]

In May 2010, Lil Reese pleaded guilty to burglary charges and was given two years of probation.^[7]

On October 24, 2012, a video allegedly showing Lil Reese assaulting a woman was posted to the internet.^[2] On April 28, 2013, Lil Reese was arrested by Chicago Police on a warrant issued two days earlier, based on criminal trespass to a residence with persons present, battery, and mob action from the video incident from February 2012.^[1][7]

On June 23, 2013, Lil Reese was arrested in Chicago and charged with motor vehicle theftafter an incident on April 13, 2013, where he was not able to provide proof of ownership for a BMW 750Li.^[8] However, the charge was later dropped. On July 13, 2013, Lil Reese was arrested again in Chicago for marijuana possession, a violation of his probation.^[9]

In May 2022 Reese was arrested for aggravated assault in Houston Texas. He was released in January 12, 2023 after serving 7 months in Harris County Jail.^[10][11]

On November 11, 2019, Taylor was shot in the neck and critically wounded^[12] at a busy intersection in the area of Markham and Country Club Hills. Country Club Hills police responded to 167th Street and Pulaski Road around 2:30 p.m. Witnesses told police Taylor was pursued by a driver of another car during a chase. Witnesses reported hearing as many as 12 gunshots during the chase. The driver of that vehicle got out of his car and shot the man with what witnesses called a small rifle and then fled the scene.^[13]

On November 18, Taylor sent out information about being released from the hospital and that he survived the shooting and is "Alive and Well".^[14] A day after leaving the hospital, he released a new song "Come Outside".^[15]

In March 2020, during the COVID-19 pandemic, Taylor posted a controversial message on Twitter: "Chinese people nasty asl man got the whole [world] fuck up".^[16] Many condemned him, calling his tweets racist. Taylor faced immediate backlash for his comment; many asked him to delete the tweet. After his Twitter account was suspended, he went on Instagram to post a screenshot of the official violation notification from Twitter with the captions, "Lol Look how the Chinese people did my Twitter".^{[17][better source needed]}

On May 15, 2021, Taylor and two other men were injured in a shootout at a parking garage in Chicago and were taken to Northwestern Memorial Hospital.^[18] His eye was grazed by a gunshot; he and another one of the men, who was shot in the knee, were later listed in fair to good condition, and the third in critical condition with multiple wounds to the torso.^[12] The shooting was reportedly over a stolen Dodge Durango.^[19]