The Date: October 22, 2009
The Event: Wayne pleads guilty to attempted criminal possession of a weapon and is scheduled to be sentenced to a one-year jail sentence in February 2010.
The Date: February 9, 2010
The Event: Extreme dental surgery delays Lil Wayne's original sentencing date and he is forced to wait until early March for a new sentencing hearing.
The Date: March 2, 2010
The Event: A fire at the Brooklyn courthouse where Wayne is scheduled to be sentenced postpones his hearing—twice!—and he is forced to wait to be sentenced again.
The Date: March 8, 2010
The Event: Lil Wayne is formally sentenced to one year in prison and is placed into protective custody at Riker's Island.
The Date: April 2, 2010
The Event: Wayne posts a blog called "Gone 'til November..." on his fan site, WeezyThanxYou.com. Throughout the course of his sentence, Weezy posts a total of 10 blogs for his fans and two sports-related blogs called "Tune's Sports Corner."
The Date: April 28, 2010
The Event: Diddy surprises Wayne at Riker's Island by visiting with him for an hour. Later, during a November 2010 interview with Billboard, Wayne praises Diddy for cutting through the prison's red tape and making the trip to see him.
The Date: April 29, 2010
The Event: A female guard at Riker's Island files a lawsuit against the city of New York, claiming she was forced to admit that she was spying on Wayne after making an unscheduled trip to Wayne's unit during his early days in the prison.
The Date: May 11, 2010
The Event: Wayne is found to be in possession of an MP3 player and headphones (aka "music contraband") and has both of them confiscated from his cell with punishment pending.
The Date: June 2, 2010
The Event: During a listening session for Drake's debut, Thank Me Later, he reveals that he recently visited Wayne in prison. He also reveals that Wayne may appear on a remix to a song from the album.
The Date: June 9, 2010
The Event: Wayne records a verses for Drake's "Light Up" from prison. Drake shares the verse with his fans on Ustream and includes it on the song's official remix alongside Jay-Z.
The Date: June 18, 2010
The Event: Eminem drops his seventh album, Recovery, featuring a guest spot from Wayne on the Just Blaze-produced track, "No Love." He later appears in a video for the song.
The Date: June 22, 2010
The Event: Wayne enters a plea bargain via video link in another legal incident in Arizona which involved the U.S. border control finding cocaine, Ecstasy and a handgun on his tour bus back in 2008. Wayne pled guilty to one count of possession of a dangerous drug and will face three years of unsupervised probation as a result.
The Date: July 8, 2010
The Event: Just hours before taking a trip to Greenwich, Conn. to support close friend LeBron James during The Decision, Kanye West stops off at Riker's Island to visit Wayne. He reportedly raps his entire album, My Dark Beautiful Twisted Fantasy (then known as Good Ass Job), during the visit.
The Date: August 3, 2010
The Event: Wayne calls Funkmaster Flex's Hot 97 show to do his first and only radio interview from prison.
The Date: August 19, 2010
The Event: The video for Drake's single, "Miss Me," featuring Lil Wayne, is released. It features clips of Wayne shot prior to his imprisonment. Drake also confirms a Lil Wayne homecoming concert on November 5 during a Ustream session on the same day.
The Date: September 6, 2010
The Event: A female guard at Riker's Island is questioned for "spending extra time" with Wayne and "letting him hang out in his cell while other inmates were locked out of their bunks and ordered into the recreation yard."
The Date: September 11, 2010
The Event: Wayne's Riker's Island I.D. and inmate records leak online.
The Date: September 27, 2010
The Event: Wayne's label Young Money releases I Am Not A Human Being, a digital album full of songs the rapper recorded prior to going away to prison. A physical copy of the album also hits stores on October 12 and sails to the top of the U.S. Billboard 200 chart.
The Date: September 28, 2010
The Event: During an interview with Rolling Stone, President Barack Obama admits that he now has "a little Lil Wayne" on his iPod thanks to his personal aide Reggie Love. He does not mention the rapper's current incarceration.
The Date: October 4, 2010
The Event: Wayne is placed into solitary confinement for the remainder of his sentence as punishment for his possession of an MP3 player earlier in his bid.
The Date: October 27, 2010
The Event: A 20-year veteran guard at Riker's Island is suspended without pay for 10 days after making an unscheduled 45-minute visit with Lil Wayne in solitary confinement.
The Date: November 3, 2010
The Event: Former President of the United States of America Bill Clinton says that he's excited for Wayne's impending release from Riker's Island during a radio interview.
The Date: November 4, 2010
The Event: Wayne is released from Riker's Island after spending almost eight months behind bars. The first photo of him leaks to the Internet courtesy of DJ Scoob Doo and a tweet he posts at 3pm simply reads, "aaaaaaahhhhhhmmmmm baaaaakkkkkkkkkk."
What do you think Lil Wayne will do now that he's free from prison? Leave us a comment in the box below and let us know!