Lil Bibby’s Evolution: From “Free Crack” Mixtapes to Grade A Productions & the Juice WRLD Era

Bio/Wiki
NameBrandon George Dickinson 1
Stage Names / NicknamesLil Bibby, Bibby 2
Date of BirthJuly 18, 1994 2
Age (as of Sept 17, 2025)31 (derived from July 18, 1994)
Zodiac SignCancer (derived from July 18)
NationalityAmerican 2
HometownChicago, Illinois – South Side 2
Physical Stats
Height~5’10″–6’1″ (estimated, unconfirmed)
Weight~170–190 lbs (estimated, unconfirmed)
Eye ColorBrown (assumed from media photos)
Hair ColorBlack (assumed from media photos)
Career
Debut SongEarly breakout “Kill Shit” with Lil Herb (2012–2013) and first solo single “How We Move” (2013) 3
Breakout Tape / EPFC3 The Epilogue EP, Kemosabe Records, 2017 4
Collaborations
  • “We Are Strong” with Kevin Gates (2014) 5
  • Juicy J – “Low” feat Nicki Minaj, Lil Bibby & Young Thug (2014) 6
  • A Boogie wit da Hoodie – “Proud of Me Now” feat Lil Bibby 7
  • Meek Mill & PnB Rock – “Some How Some Way” feat Lil Bibby 8
Labels / ImprintsFounder – Grade A Productions; previously Kemosabe Records / RCA 9
SignatureNot publicly available
Personal Life
SiblingsBrother – George “G Money” Dickinson, Grade A co-founder 10
Education
SchoolLiberty High School, Chicago – graduated 2015 11
CollegeExplored computer engineering, discussed enrolling 12
Educational QualificationHigh school graduate; college not confirmed 11
Preferences & Interests
Food HabitNot publicly stated
HobbiesStudio work, basketball, music business 13
Earnings & Assets
Net WorthNot publicly disclosed; estimates vary 10
Income SourcesMusic releases, features, executive work at Grade A Productions
Controversy / Notable Moments
OverviewOversight of Juice WRLD’s posthumous catalog, including protecting “In My Head” from leaks 14
Fun Facts
  • Completed high school later in career while already famous
  • Known for gravelly mature voice even as a teen
  • Pivoted to become label executive co-founding Grade A

Who is Lil Bibby and what is his real name?

Lil Bibby is Brandon George Dickinson a Chicago rapper who became a label executive.

Lil Bibby whose real name is Brandon George Dickinson is a Chicago born rapper who rose during the early 2010s drill movement before moving into a successful executive role 15 He grew up on the South Side of Chicago and that shaped his raw street centered lyrics. His breakout came with the “Free Crack mixtape” series where his gravelly voice and grounded delivery stood out from other drill artists.

Beyond rap he co founded Grade A Productions label that signed global stars like Juice WRLD and The Kid Laroi. This shift turned him from a rising rapper into a builder of international talent.

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Where did Lil Bibby grow up and how did Chicago shape his music?

A split graphic of Lil Bibby sitting on a bed, paired with a South Side Chicago street backdrop. The right side features a bold fact card with details about his upbringing, themes of survival and loyalty, grounded street realism sound, and a quote: “When you hear me, you hear the South Side.” Neon orange and white accents with city skyline and mic icons decorate the dark concrete background.
Lil Bibby’s South Side Chicago roots shaped his raw voice, loyalty-driven themes and street-grounded rap style.

Lil Bibby grew up on the South Side of Chicago and the city shaped his voice and stories.

In early interviews, he spoke about rough surroundings and how the neighborhood influenced him. That background explains the grounded tone in his songs and the focus on survival, loyalty and risk 16

When people listen to Bibby they hear the South Side in his sound. It is not just about beats or hooks, It is about the truth of growing up in an environment that demanded toughness and clarity.

What is in Lil Bibby’s Free Crack mixtapes and what do the tracks mean?

Digital timeline graphic of Lil Bibby’s Free Crack mixtape trilogy. Left block: 2013 Free Crack with heavy drums, South Side realism, video “Change.” Middle block: 2014 Free Crack 2 with bigger features and street stories. Right block: 2016 Free Crack 3 showing polish and versatility, moving past drill-only label. Dark neon-themed background with mixtape covers and Bibby’s photo on the right.
Lil Bibby Free Crack Mixtape Series (2013–2016) showcasing his rise from drill realism to broader rap recognition.

The Free Crack series built his name and laid out his core themes.

The first release “Free Crack” in 2013 set the tone with heavy drums and sharp details about life on the South Side. His voice sounded older than his age. Listeners and critics linked the project to the drill movement while noting influence outside drill 17

With “Free Crack 2″ and “Free Crack 3″, he stayed close to street stories yet widened the sound and collaborators Reviews highlighted more polish and versatility and said he was moving past a narrow drill label 18

Across the series you hear pride pressure the cost of ambition and the idea that fame does not erase fear. The video for Change released soon after the first tape captured the raw mood of that time 19

Discography

Infographic titled “Lil Baby Discography Wall (2017–Present)” featuring Lil Baby’s portrait alongside album and mixtape covers: Perfect Timing (2017, with Marlo), Harder Than Ever (2018), Street Gossip (2018), My Turn (2020), The Voice of the Heroes (2021, with Lil Durk), It’s Only Me (2022), and Too Hard (2017 mixtape).
Lil Baby Discography Wall (2017-Present)
Title / ProjectDetails
Free Crack (2013)Debut mixtape that introduced his deep-voiced Chicago street storytelling and set the tone for his rise.
Free Crack 2 (2014)Second installment with tighter production and bigger collaborations; showed polish beyond an early breakout.
Free Crack 3 (2015)Third tape that pushed past a strict “drill” label with broader themes and more refined songwriting.
Big Buckz (2016)Concise EP that highlighted focused hooks and A&R instincts emerging alongside his artist run.
FC3: The Epilogue (2017)Companion EP to the FC3 era, collecting select cuts that bridged his mixtape chapter and executive pivot.
Free Crack 4 (TBA)Long-teased follow-up often mentioned in interviews; unreleased as of now but remains a fan-watched title.

Why did Lil Bibby stop rapping and switch to a label executive role?

He stopped rapping to scale his impact by building artists and running a label.

Around 2019, he explained that music for him was more than recording songs. He enjoyed finding new voices shaping their path and helping them reach full potential 20

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As an executive, he could guide young artists sign deals and build a team that could compete on a global level. He helped launch Juice WRLD and The Kid Laroi which proved his instinct for talent.

For Bibby the move was about scale and focus He chose a future where he could launch many careers instead of only his next project.

When did Grade A Productions start and who runs it?

Grade A Productions started in 2017 and Lil Bibby runs it.

He created the label after learning from his own time as an artist. He wanted structure and guidance for new talent The label was built with support from his brother and close family.21

“I knew how tough it was coming up without guidance, so when I started Grade A I wanted to give artists structure, a real plan, and the support I didn’t have. It’s not just about dropping music, it’s about making sure they’re mentally right, financially straight, and building something that lasts.”

Bibby leads scouting and long term planning. He focuses on career building mental health and smart pacing so artists avoid common mistakes.

Grade A is known for backing Juice WRLD and The Kid Laroi and that track record shows how Bibby grew into a trusted label head.

How did Lil Bibby discover Juice WRLD and what happened after?

Infographic timeline titled “Lil Bibby & Juice WRLD Discovery & Breakthrough” featuring Lil Bibby’s photo, neon blue icons, and silhouettes representing Juice WRLD and the breakthrough moments: 2017–2018 discovery on SoundCloud, March 2018 Grade A + Interscope deal, and 2018–2019 hit singles and #1 album success.
Lil Bibby & Juice WRLD Discovery & Breakthrough

He saw Juice rising online and closed a Grade A and Interscope deal in March 2018.

Through Grade A Productions he moved fast and by March 2018 Juice signed a major deal with Interscope in partnership with Grade A This turned the label from a small indie into a power player 22

What followed was a historic run, Hit singles, a number one album and cross scene influence Bibby worked closely with Juice to keep the music creative and consistent.

The 2018 breakthrough is the core of their story and shows how vision and talent met at the right time.23

What did Lil Bibby do with Juice WRLD’s posthumous releases?

He protected the legacy and released only strong music with the family and Interscope.

After December 2019, Bibby led Grade A with Juice’s family and Interscope to handle the music with care. The goal was to honor intent and keep quality high. 24

“With Juice’s music, we only put out what feels powerful and true to him. I sit with his mom and the team on every decision, because the point isn’t to rush or exploit, it’s to make sure his legacy stays pure and the fans hear the best of what he left behind.”

Righteous arrived in April 2020, Then in July 2020 “Legends Never Die” debuted at number one. In December 2021 “Fighting Demons” released alongside the HBO film “Into the Abyss”. Later came “In My Head” in 2022 and a five year edition of Legends Never Die in 2025 25

Bibby has said the team releases only music that feels strong He worked with Juice’s mother Carmela Wallace on decisions so the album would not feel rushed or exploited 26

How is Lil Bibby connected to The Kid Laroi and how did that deal happen?

In 2019, Grade A partnered with Columbia to bring The Kid Laroi to the US market.

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“When I first heard Laroi, I saw the same hunger and raw talent I saw in Juice. Bringing him over and locking in with Columbia was about giving him the stage he deserved. I knew if we gave him the right team and structure, he could go from local buzz to worldwide.”

Laroi moved from Sydney buzz to a global stage. The connection also ran through Juice WRLD who mentored Laroi on tour Bibby guided the label side so Laroi could grow past early singles.27

The deal proved Grade A could scale its scouting beyond the United States. The model was simple, Find young voices with global potential and pair them with major partners.

What is Lil Bibby’s rap style drill or trap and how did it evolve?

He began in drill and then blended styles while keeping the same grounded voice.

Early songs placed him inside the Chicago drill wave, Yet he pushed back on strict labels and wanted freedom to experiment.

“People called it drill, some said trap, but I never cared for the box. My sound came from the streets I grew up in, and over time I just added more melody and different vibes. What mattered was keeping my voice real, the tone that made fans connect from the start.”

By Free Crack 3 reviewers heard more melody and different tempos while the blunt storytelling stayed in place.18

What never changed was his delivery and tone, that consistency let him grow without losing identity.28

Which Lil Bibby collaborations and features should fans revisit?

 

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Start with a few strong placements that still bring search interest.

“We Are Strong” with Kevin Gates from the “Free Crack 2 window shows strong chemistry between Chicago grit and Southern intensity

Around the Free Crack 3 era he worked with Future Metro Boomin Jeremih R Kelly and Common which showed reach across rap and R and B 29

“Proud of Me Now” by A Boogie wit da Hoodie featuring Lil Bibby connects him with a crossover audience.30

“How We Move” featuring King Louie captures early Chicago energy with a hook that sticks.31

Where can you legally stream Lil Bibby’s music and mixtapes?

Use Apple Music Spotify and YouTube for legal listening.

Apple Music carries the full Free Crack catalog along with FC3 The Epilogue and a profile page for singles and features.32 Spotify has official albums and collaborations, YouTube hosts official videos and label uploads.

These platforms are reliable and they support the artist and the label.

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