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UPDATE: As of May 26th, 2016, Gucci Mane has been released from prison.
When we talk about Gucci, it’s never about what he did or how long he’ll be gone for, it’s always about when he will get out.
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Timeline:
May 2005: During the height of his beef with Young Jeezy, five men attempted to rob Gucci Mane due to song lyrics that placed a bounty on the rapper’s ice cream cone chain for $10,000. The men attempted to ambush Gucci, a scuffle transpired, in an alleged attempt to defend himself Gucci acquired a gun and shot at his assailants, ending the robbery and killing one man, Henry Clark III, better known as Pookie Loc. He would post the $100,000 bail on May 24, the day his debut album Trap House was released. In January of 2006, the murder charge was dropped due to insufficient evidence.

July 2005: Gucci Mane is arrested in Miami for an assault that occurred earlier that month. The altercation involved a club promoter that was visiting Big Cat Records, the label that Gucci was signed to at the time. The promoter claims that an argument ensued between him and Gucci, and that when he turned his back Gucci struck him with a pool stick and continued to strike him once he fell to the ground. He was found guilty of aggravated assault and aggravated assault with a deadly weapon for that incident and was sentenced to six months in prison. He was in jail for that assault charge when the murder case involving Pookie Loc was dismissed.

September 2008: Gucci was arrested for only completing 25 out of 600 community service hours from the 2005 assault case.

November 2009: Gucci would go back to court for another parole violation and leave in handcuffs. He would serve until May 2010. His major label debut album, The State vs. Radric Davis, was released on December 8, through Warner Bros. Records.

November 2010: An off-duty officer notices a white Hummer driving recklessly down Northside Drive and reported the vehicle. When officers finally caught up to the vehicle Gucci and an unnamed man were arguing outside a body shop. The officers attempted to intervene. Gucci ignored them and punched the man he had a dispute with, which eventually lead them to pepper spraying Gucci. He would be booked under various charges: damage to government property, obstruction, driving without a license, reckless driving, running a red light or stop sign, failure to maintain a lane and driving on the wrong side of the road.

January 2011: The Superior Court of Georgia’s Fulton County ordered Gucci Mane to a psychiatric hospital due to the mental incompetence filing. ”On January 13, a few days after he was released, Gucci would get his infamous ice cream cone face tattoo.

April 2011: Gucci is arrested while visiting his parole officer for an incident where he pushed a woman out of a moving vehicle back in January. Outside of South DeKalb Mall, Gucci approached the woman in his white Hummer and asked if she wanted breakfast. The woman claims Gucci offered her $150 for sex and when she refused he forced her out of the moving truck.

On September 13, Gucci was sentenced to six-months in county jail after pleading guilty to two counts of battery, two counts of reckless conduct and one count of disorderly conduct. He gave an interview with XXL the very next day, he was optimistic about his future believing that it would be his very last time in jail.

March 2013: Atlanta police issued a warrant for Gucci’s arrest after allegedly attacking a fan who attempted to get a picture with him. James, a soldier who was in attendance at the Harlem Nights club, was speaking to Gucci’s security guard outside of V.I.P about snapping a picture with the artist when Gucci attacked him with a champagne bottle.

March 2013: It wasn’t until the very end of March that Gucci turned himself in for the aggravated assault charges. He was denied bond and appeared back in court on April 10, where he was indicted on one count of aggravated assault. Two days later he posted the $75,000 bail but he wouldn’t be free for long. The next day he was arrested again for violating his parole.

September 2013: A late night with a friend leads to Gucci being arrested. Both these situations happen the same week as Gucci’s legendary Twitter rant and his fight inside of Atlanta’s Lennox Mall.

September 30, 2013: It's announced that Gucci would be charged with firearm possession by a convicted felon, disorderly conduct, carrying a concealed weapon, marijuana possession, and probation violation. He would serve 183 days in jail for the charges.

December 2013: Gucci Mane is charged in federal court with two counts of possessing a firearm as a felon.

May 2014, Gucci pleads guilty to possession of firearms by a convicted felon. He agrees to a plea deal which impacts his sentencing immensely.

January 2016: 1017 Instagram post caption that says Gucci will be free in March of this year.