By Scott Tomford | MOG Associate Editor

After four months of mounting fear, Weezy day is almost upon us. Today, Lil Wayne was supposed to begin his one-year jail sentence at Rikers Island (it was delayed early this afternoon for medical reasons). The sentence, stemming from a gun-possession charge, has a fairly unique place in hip-hop history. While many popular rappers have gone to jail, it's a rare that they go out at their peak. It's bad enough that the sentence will bring Weezy's rapid-fire output to a grinding halt, but he's also doing it at a time when the Internet makes a year seem like a millennium.

With a million question marks surrounding how Lil Wayne's time in jail will pan out and how it will affect his place in pop culture, we examine the effect similar stints have had on a slew of his friends and enemies.

The Rapper: Pimp C of UGK

The Rap Sheet: Though his conviction was for a different charge, Pimp C's sentence came at a vital time in UGK's career, just as the group was on the cusp of recapturing the success that came with Jay-Z's "Big Pimpin'". Pimp C spent the next three years incarcerated, finally getting out at a time when the public more or less forgot about UGK's previous successes.

The Lesson: The most important one from a hip-hop perspective is UGK's ability to revitalize and reinvent itself once Pimp C was freed, proving that a rapper's relevance can survive time spent outside of society. The other lesson is a bit more of a cautionary tale: less than two years after gaining freedom, Pimp C died from using "drank," the mix of promethazine and cough syrup that has fed Lil Wayne's on-again, off-again addiction. Keep it at bay Weezy, and this time, come out 100% clean.

The Rapper: Mystikal

The Rap Sheet: The rapper most famous for 2000's inescapable "Shake Ya Ass," Mystikal beefed with Lil Wayne and the rest of the Cash Money crew when they were climbing the ranks in the late '90s. However, while Weezy evolved his sound throughout the '00s, Mystikal's repeated offenses meant his jail sentence kept expanding. He got out last month... after six years behind bars.

The Lesson: Mysti-who? Ten years on and the rapper's style seems both stilted and full of unrealized potential. Maybe the lesson is that Lil Wayne should thank his stars he's only gone for a year and be sure to stay on his best behavior.

The Rapper: Prodigy

The Rap Sheet: Like Lil Wayne, Prodigy was arrested on gun possession charges, though his sentence is about two years longer than Wayne's. Despite that, he's managed to stay in the spotlight both by regularly writing letters about the state of hip-hop and constantly hyping his many yet-to-be-made projects.

The Lesson: Have you seen Prodigy's letters?! Pardon our French, but the dude has lost his damn mind, bringing up constant paranoid thoughts about Jay-Z and the Illuminati, trying to start a feud with Crooked I, and claiming current hip-hop fans are stupid. Lil Wayne has described himself as crazy, but in a "great way," meaning not the kind of crazy Prodigy is going to be remembered for. Let's keep it that way. Keep in touch, but keep from going crazy.

The Rapper: T.I.

The Rap Sheet: As with Prodigy and Lil Wayne, so goes T.I. The rapper's current stint in jail is for about same amount of time as Lil Wayne's, and T.I.'s popularity was near its own peak when he went in.

The Lesson: Pay close attention when T.I. gets out of jail this March... his further rise or fall could provide either a blueprint or cautionary tale to follow when Lil Wayne is out. T.I. plans on releasing an album shortly after his release just as Tha Carter 4 could see release days before Weezy's own release.

The Rapper: 2Pac

The Rap Sheet: If there's one name that keeps coming up in reference to Lil Wayne's jail time, it's Tupac Shakur. Peaking just as he started a sentence that turned out to last just under a year, Shakur's high-profile incarceration included releasing an album that debuted at number one on the charts, a marriage, and several other incidents that kept him on the radar.

The Lesson: Shakur provides the best possible example of a rapper staying popular in jail. What's more, he didn't actually peak before jail: his true masterpiece and best-selling record, All Eyez on Me, was made just after his sentence was completed.

Unlike Shakur, though, Lil Wayne has an uphill battle to fight. In an age where both pop culture and music both evolve at a near-daily pace, a year away from the game could prove to be fatal to someone that isn't resourceful in every sense of the word. Reports from experts claim that Lil Wayne's hopes to bring an iPod full of beats to jail will be denied, leaving him with yet another roadblock. But until we know the reality of his life behind bars, it's not wise to underestimate Weezy.

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