In 2013, Lil Bibby released his debut mixtape, Free Crack. He cited Drake and Jadakiss as two of his favorite rappers. Vice stated that the mixtape was apparent in both rappers' influences.^[3] The mixtape features guest appearances from fellow Chicagoans Lil Herb and King L, while productionwas handled by Hit-Boy, Young Chop and The Olympicks, among others.^[4] DJ Scream hosted this mixtape. The tape combines his distinctive gruff and imposing voice, along with a solid delivery and flow.^[5] Music videos were released for the songs "How We Move" (featuring King L), "Change", "Water" and "Tired of Talkin'".

In December 2013, in an interview with XXL, Bibby hinted that the next step for his career could be an EP.^[6] In 2014, it was also stated, that the rapper Drake was a huge fan of Bibby and that they'd spoken in 2013, before the release of Bibby's debut mixtape. Bibby said it pushed him onto improve his debut release, adding the tracks "Water" and "Whole Crew".^[6]

In January 2014, Bibby appeared on Sway's radio show Sway in the Morning. On the show he spoke about the success of his debut mixtape, and also dropped a live freestyle.^[7] During the same month, Bibby also featured on New York's radio station, Hot 97.^[8] During the same month, Bibby stated in his interview with Billboard, that he was working on material for an EP, but was waiting on a couple of features.^[9] Bibby also appeared on the list of 2014's XXL Freshman Class.^[10] He was the last person selected to the list, due to Young Thug's last minute cancellation.

In August 2014, he guest featured alongside Young Thug and Nicki Minaj on Juicy J's single "Low," and was later featured on the remix of Kid Ink's "Main Chick."^[11][12] After a few delays, Bibby's sophomore mixtape, Free Crack 2, was released on August 29, 2014. Hosted by DJ Drama, includes guest appearances from Lil Herb, Wiz Khalifa, Juicy J, Kevin Gates, Jadakiss and Anthony Hamilton, among others. The mixtape has production from Juicy J, Honorable C.N.O.T.E., Sonny Digital and DJ Pain 1, among others. It was released for free digital download and rapidly accumulated over 120,000 downloads.^[13]

Free Crack 2 was received with critical acclaim. XXL magazine awarded the mixtape an XL, praising the mixtape's authenticity, catchy hooks and production, while also commenting that the mixtape showcases Bibby's "growth as an artist."^[14] RedEye awarded the mixtape three stars out of four, commenting on the tape's maturity and versatility and praising the ability of the song 'Dead or in Prison' to let Bibby's "emotion and natural charisma do the heavy lifting."^[15] BETgave the mixtape a positive review, awarding it five stars while commenting on its "new level of depth and introspection, detailing the difficult balance of fame and authenticity and how that effects everyday life in some of America's urban war zones."^[16]

In 2015, Lil Bibby received his high school diploma. Initially, he had opted for a GED and after completing the necessary coursework (with straight A's), he decided to re-enroll in high school. His alma mater was from Chicago's Liberty High School.^[17] A year later, after several universities had offered him scholarships, Bibby considered studying Computer Engineering at a university, although he ultimately decided against this.^{[18][19][20][21][22]}

In 2015, Bibby released two singles "Ridah" and "Aww Man" (featuring Future) for an upcoming album, supposedly the fourth installment in his Free Crack series.^[23] Both singles failed to reach any domestic charts. In late 2016, Bibby released "Thought It Was A Drought", which was produced by DJ L Beats and Roberto Mario.^{[citation needed]}After a long period without any releases, in early 2018, Bibby began using the hashtag "Free Bibby" on social media, protesting his label's refusal to allow him to release the project.^[24]

Bibby, with the help of his brother George "G-Money", launched their own record label known as Grade A Productions. In an interview with XXL, Bibby discussed his transition from being a rapper to starting a record label: 

"I really don't know. I like to make people a lot of money. I got enough knowledge and I've studied this rap stuff and I got enough relationships to help an artist, help his family [and] I get a kick out of it 'cause I see how the label does it and my situation. I feel like just helping people."^[25]

In 2017, they discovered then upcoming American rapper Juice Wrld after hearing his song "Lucid Dreams". Under the label, Juice Wrld released his debut studio album Goodbye and Good Riddanceon May 23, 2018, which was followed by three singles "All Girls Are the Same", the aforementioned "Lucid Dreams", and "Lean Wit Me". In March 2019, Juice WRLD released his second studio album Death Race for Love which was followed by two singles "Robbery", and "Hear Me Calling". 

In 2019, Bibby later discovered upcoming Australian rapper and singer The Kid Laroi after hearing his song "Blessings" from his debut EP 14 With A Dream. In March of that year, Bibby signed Laroi to Grade A. Under the label, Laroi released his debut mixtape F*CK LOVE in July 2020, spawning two singles: "Go" featuring labelmate Juice Wrld (a posthumous verse due to his death in December 2019), and "TELL ME WHY". On November 6, Laroi released a deluxe edition of F*ck Love titled F*ck Love (Savage) which was followed by the single "SO DONE".^{[citation needed]}

On December 8, 2019, Juice Wrld suffered from an overdose at an airport in Chicago which led to his unexpected death. On January 22, 2020, Grade A announced that posthumous projects from Juice Wrld will be released to honor his legacy. His first posthumous album Legends Never Die was released in July of that year, which contained three singles "Righteous", "Tell Me U Luv Me" featuring Trippie Redd, and "Life's A Mess" featuring Halsey. In December 2021, it was followed up with his second posthumous album Fighting Demons. Throughout 2020, other posthumous releases from the artist included "Smile" with The Weeknd, "Real Shit" with Benny Blanco, "Reminds Me Of You" and "Bad Boy" with Young Thug in 2021.^{[citation needed]}

On May 27 2021, Bibby announced Juice Wrld's third and final posthumous album, The Party Never Ends. On September 9 2024 The Party Never Ends was officially announced, with Pre Party released. Pre Party consists of two songs. Its supposed lead single, "Lace It" (with Benny Blanco and Eminem) was released in December 2023.^[26]