Cortez Bryant knows the exact time.

The Lil Wayne brand may be large, he knows, but it’s time to kick another sales/touring goal to keep the juggernaut soaring.

The colorful New Orleans rapper was released Nov. 4, 2010 from New York’s infamous Rikers Island jail complex after serving 8 months in a gun case. He is the first artist in 15 years to release a #1 album—"I Am Not a Human Being"—on the Billboard 200 chart while serving a sentence.

Prior to jail, Lil Wayne reportedly grossed over $50 million in 2009.

Bryant Management works with Hip Hop Since 1978, operated by rap moguls Kyambo “Hip Hop” Joshua and Gee Roberson (who had shared head-of-A&R duties at Jay-Z's Roc-A-Fella Records) to collectively manage Lil Wayne, dynamic Canadian rapper Drake and producer Kane.

Bryant Management and Hip-Hop Since 1978 keep separate staff, offices and clients, save for Lil Wayne and Drake. Hip Hop Since 1978 also manages Young Jeezy, Kanye West, and producer Noah “40” Shebib.

Bryant Management also handles Texan teenage rapper Lil Twist.

Bryant is also co-president (with Mack Maine) of Young Money, an imprint of Cash Money Records, which is the label home of Drake and Lil Twist. Also on Young Money are Nicki Minaj, Tyga, Jae Millz, Cory Gunz, Lil Chuckee, and Short Dawg.

Three years ahead of Lil Wayne (then Dwayne Michael Carter Jr.) at the Eleanor McMain Secondary School in New Orleans, Bryant led the school band’s cymbal section. When Wayne joined, Bryant took him under his wing. However, Bryant tried to discourage Wayne’s rap ambitions.

Bryant went on to earn a mass communications and graphic design degree from Jackson State University, a historically black university in Jackson, Mississippi. Being full-time in music didn’t enter his mind until his senior year, when he received a request from Wayne to oversee his career.

At a career crossroads, Wayne needed a manager he could trust. Bryant accepted the challenge and has since guided his former classmate’s career as he emerged as one of the most important performers in contemporary hip hop.

In the mid ’90s, New Orleans was mocked as a hip hop backwater. The rise of Cash Money Records, and Master P’s No Limit label in the late ‘90s changed that perception.

Wayne was nine when he caught the ears of Cash Money’s co-founder Bryan “Birdman” Williams. The youngster turned up at Cash Money’s autograph signings, and rapped into William’s answering machine.

In 1995, the label signed the 13-year-old along with young rappers B.G., and Juvenile. Lil Wayne appeared on B.G.'s album "True Story" the same year. Two years later, Lil Wayne, Juvenile B.G., and Turk formed the group the Hot Boys that would become the label's most well known act.

At 17, Lil Wayne released his first solo album, “Tha Block is Hot” in 1999. It was followed by “Lights Out” in 2000; both sold over a million units. However, his third solo album, "500 Degreez” had disappointing sales. Meanwhile, the Hot Boys imploded as B.G. and Juvenile departed Cash Money.

In 2005, Lil Wayne dramatically stepped out from the Hot Boys’ shadow as his album “Tha Carter II,” the follow-up to the original 2004 “Tha Carter” album, debuted at #2 on the Billboard 200 chart with sales of 240,000 units in its first week of release.

In 2005, Lil Wayne was named president of Cash Money. He then founded Young Money as a Cash Money imprint. However, by 2007, the increasingly busy rapper had stepped down from heading both labels, and handed management of Young Money over to Bryant.

Strategic mixtapes and guest appearances dramatically elevated Lil Wayne’s profile over the past decade. He guested on tracks with Destiny’s Child, Fat Joe, Kanye West, Kid Rock, Fall Out Boy, Gym Class Heroes, Chris Brown, Madonna and Shakira. He also released a flood of new songs online via semi-official mixtapes.

In 2008, Lil Wayne solidified his status as rap’s most celebrated artist. He had the best-selling album of the year and won a Grammy Award for his 6th solo album, “Tha Carter III” which sold a whopping 3.5 million units.

Managing Lil Wayne, however, suddenly became more challenging.

In January 2008, Lil Wayne’s tour bus was stopped at a U.S. Border Patrol checkpoint outside Yuma, Arizona. A search yielded marijuana, cocaine, and Ecstasy. Officials also found a .40 caliber pistol registered to Lil Wayne who had a concealed weapons permit in Florida. Felony drugs and weapons charges were filed against him.

In October, 2009, Lil Wayne pled guilty to having a loaded gun on his tour bus after a Manhattan concert in 2007. He began serving his one-year sentence in March 2010.

While Wayne was in Rikers, a plea deal was reached for the 2008 arrest. He was sentenced to three years of unsupervised probation and no jail time due to the deal, which had him plead guilty to one count of possession of a dangerous drug in exchange for the dismissal of other drug and weapons charges.

Following jail, Lil Wayne quickly returned to business. He immediately began recording at The Hit Factory studio in Miami. He returned to the concert stage in Las Vegas on November 6, 2010 at Drake’s final show of his U.S. tour; Wayne performed “Miss Me” with his surprised protégé.

Meanwhile, with the world—including presidents Barack Obama and Bill Clinton who have both name-checked him recently-- waiting to hear Lil Wayne’s “Tha Carter IV,” which will now be all fresh-out-of jail material, Bryant is checking his watch hourly.

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