Challenges in the Life of Lil Wayne in a Detailed Timeline

A closer look at the defining struggles that shaped Lil Wayne's life and career.

Dwayne Michael Carter Jr., known as Lil Wayne, is a highly influential American rapper. Discovered by Birdman in 1993, he signed with Cash Money Records at age eleven and became the label's flagship artist. Lil Wayne is often considered one of the greatest and most influential hip hop artists of his generation.

Sections (6)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Controversies & Scandals

January 2006: Divorce from Toya Johnson

In January 2006, Lil Wayne and Toya Johnson divorced due to his lifestyle and communication with former romantic partners.

2006: Miscarriage and Growing Distant

In 2006, Trina suffered a miscarriage from what was later confirmed to be her and Lil Wayne's unborn child, and they grew distant from one another. During that time Trina developed an affair with Young Buck.

July 22, 2007: Arrest in New York City

On July 22, 2007, Lil Wayne was arrested in New York City after police discovered him and another man smoking marijuana near his tour bus. A .40 caliber pistol was found nearby, leading to charges of criminal possession of a weapon and marijuana possession.

October 5, 2007: Arrest in Boise, Idaho

On October 5, 2007, Lil Wayne was arrested in Boise, Idaho, on felony fugitive charges based on accusations from Georgia authorities of possessing a controlled substance. These charges were later dropped due to a "mix-up".

January 23, 2008: Arrest near Yuma, Arizona

On January 23, 2008, Lil Wayne was arrested near Yuma, Arizona, after Border Patrol agents found marijuana, cocaine, ecstasy, and $22,000 in cash on his tour bus. He was charged with multiple felonies, including drug possession and misconduct involving weapons.

May 6, 2008: Court Appearance in Arizona

On May 6, 2008, Lil Wayne appeared in court in Arizona and pleaded not guilty to the drug charges stemming from the January 23 arrest.

July 24, 2008: Copyright Infringement Lawsuit

On July 24, 2008, Abkco Music filed a lawsuit against Lil Wayne for copyright infringement related to the song "Playing with Fire" on Tha Carter III, claiming it was derived from The Rolling Stones' "Play with Fire".

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August 2008: Rumors of Reginae's Death

In August 2008, internet rumors circulated that Lil Wayne's daughter, Reginae, had died in an auto accident, which he immediately dispelled.

February 2009: $1.3 Million Lawsuit

In February 2009, Lil Wayne faced a $1.3 million lawsuit from RMF Productions after cancelling three shows for which he had received a $100,000 advance payment.

October 2009: Copyright Infringement Lawsuit Over Voice Recordings

In October 2009, Lil Wayne, Birdman, and Cash Money Records were sued for copyright infringement by Thomas Marasciullo, who claimed his voice was used without permission on "Respect" and other tracks from the album Like Father, Like Son and Birdman's 5 * Stunna.

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October 22, 2009: Guilty Plea for Weapon Possession

On October 22, 2009, Lil Wayne pleaded guilty to attempted criminal possession of a weapon in New York.

December 18, 2009: Detained at Texas Border Patrol Checkpoint

On December 18, 2009, Lil Wayne and 11 others were detained at the Falfurrias, Texas, border patrol checkpoint after marijuana was found on two of his tour buses.

2009: Breakup with Lauren London

In 2009, Lil Wayne and Lauren London broke up after London discovered she and Wayne's ex-girlfriend Nivea were pregnant at the same time.

March 8, 2010: Sentenced to Rikers Island

On March 8, 2010, Lil Wayne was sentenced to one year in jail and began serving his sentence on Rikers Island for attempted criminal possession of a weapon.

March 17, 2010: Bench Warrant Issued

On March 17, 2010, a bench warrant was issued for Lil Wayne after he failed to appear for a final trial management conference in Arizona. At the time, he was already incarcerated on Rikers Island on weapons charges.

May 2010: Contraband Found in Jail

In May 2010, Lil Wayne was found to be in possession of contraband, including an MP3 player, charger, and headphones, by Rikers Island correctional staff.

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June 2010: Engagement Called Off

In June 2010, Nivea decided to end her relationship with Lil Wayne while pregnant with their son, calling off their engagement for the second time amidst Wayne's prison sentence.

June 22, 2010: Guilty Plea in Arizona

On June 22, 2010, Lil Wayne pleaded guilty in Arizona to the drug charges from the January 2008 arrest, leading to a plea deal.

June 30, 2010: Sentenced to Probation

On June 30, 2010, Lil Wayne was sentenced to 36 months of probation as part of the plea deal in Arizona.

March 2011: Deezle Lawsuit Over Royalties

In March 2011, producer Deezle (Darius Harrison) sued Lil Wayne and Cash Money Records over unpaid royalties from the album Tha Carter III.

June 2011: Play-N-Skillz Lawsuit Over Royalties

Also in June 2011, Dallas producers Play-N-Skillz filed a lawsuit against Lil Wayne, claiming he owed them at least $1 million in unpaid royalties for "Got Money" from his album Tha Carter III.

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June 2011: David Kirkwood Lawsuit Over Royalties

In early June 2011, producer David Kirkwood filed a lawsuit against Young Money Entertainment and Cash Money Records, claiming they failed to pay him over $1.5 million in royalties and production services for his work on the album, including songwriting on "Love Me or Hate Me".

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July 2011: Done Deal Enterprises Lawsuit

In July 2011, Done Deal Enterprises filed a lawsuit against Lil Wayne, Universal Music Group, Cash Money Records, and Young Money Entertainment, alleging copyright infringement of the song "BedRock" from the album We Are Young Money, seeking $15 million in damages.

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October 25, 2012: Emergency Landing in Texas

On October 25, 2012, Lil Wayne's private jet made an emergency landing in Texas due to a medical episode. He was treated for a "severe migraine and dehydration".

November 2012: Taking Seizure Medication

In November 2012, Lil Wayne stated in an interview that he was taking seizure medication on doctor's orders due to recent incidents.

November 2012: Ordered to Pay Quincy Jones III

In November 2012, Lil Wayne was ordered to pay Quincy Jones III $2.2 million due to a lawsuit claiming that he blocked the release of Jones's film The Carter, thereby infringing on its profits.

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March 14, 2013: Seizures and Hospitalization

On March 14, 2013, Lil Wayne was treated at Cedars-Sinai Medical Center in Los Angeles after having seizures on a music video set with Nicki Minaj. He was released early hours of March 13.

December 4, 2014: Album Release Delayed

On December 4, 2014, Lil Wayne announced that Tha Carter V would not be released on its expected date due to his conflict with Birdman and Cash Money Records, who were refusing to release the completed album. He expressed feeling like a "prisoner".

January 2015: Lawsuit Against Birdman and Cash Money Records

In late January 2015, Lil Wayne sued Birdman and Cash Money Records for $51 million, marking a significant escalation in their ongoing conflict.

June 2016: Seizures During Flight

In June 2016, Lil Wayne had two seizures during a flight from Wisconsin to California, forcing an emergency landing in Omaha, Nebraska.

September 3, 2017: Hospitalization in Chicago

On September 3, 2017, Lil Wayne canceled a Las Vegas show after having a seizure and being hospitalized in Chicago, where he was brought after being found unconscious in a hotel room.

December 12, 2020: Guilty Plea to Federal Firearms Charge

On December 12, 2020, Lil Wayne pleaded guilty to a federal firearms charge in Florida after being arrested in December 2019 for transporting a loaded handgun on his private jet from California.