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Would jail stall Chief Keef's career before it starts?

Lawyers for Chicago rapper Chief Keef sparred with Cook County prosecutors on Wednesday over whether to jail the Chicago rapper for probation violations stemming from three earlier delinquencies.

Following a meteoric rise and a successful single (“I Don’t Like”) through Kanye West’s G.O.O.D. label, Keef was just signed to Interscope Records and has been in California recording tracks for a debut hip-hop album.

Would jail time stall a promising career before it starts?

Prison terms haven’t exactly slowed down some rappers’ careers. Some hip-hop stars have frequently cycled in and out of jail, releasing albums while incarcerated. Before he served time for weapons charges, T.I. dropped a single “My Life Your Entertainment” noting that he was “showered with support from my adoring fans / they hear T.I.’s arrested, they’re like, ‘Here we go again.’

Not everyone gets out in one commercial piece, though. Post-prison careers haven’t been easy to jumpstart for the likes of Slick Rick, DMX, Mystikal, Lil’ Kim and others. Here’s a look at some of the most notable jailed rappers and how they fared before and after paying their societal debts:

Tupac Shakur

Sentenced: November 1993, for sexual assault, 1.5-4.5 years; entered prison in February 1995

Before the stretch: Shakur’s solo records had started to crack Billboard’s top 50, and he’d formed a less-successful rap group called Thug Life. Shakur also was implicated in a police shooting, but charges were dropped.

After the stretch: One month to the day after entering prison, Shakur’s album “Me Against the World” was released, debuting at No. 1 — the first artist to hit No. 1 while serving time — and selling 2.5 million copies. While in prison, Shakur got married and wrote a screenplay. He was released in 1996, signed to Death Row Records, and quickly released “All Eyez on Me,” which went six-times platinum and was hailed as one of hip-hop’s best recordings ever.

Lil Wayne

Sentenced: March 2010, for weapons and drug charges, one year in prison; entered prison that month

Before the stretch: Lil Wayne started young in the group Hot Boys and grew a successful hip-hop career leading to “Tha Carter III,” the biggest-selling album of 2008. A month before his sentencing, however, his attempt at rock, “Rebirth,” debuted at No. 2 then sank due to savage reviews.

After the stretch: Free Weezy came out strong — and rapping again — with the single “6 Foot 7 Foot,” but the following album, “Tha Carter IV,” was delayed and eventually fell flat after release.


Sentenced: February 2008 and March 2009, for weapons charges, house arrest plus nine months in prison; house arrest in 2008 and entered prison in May 2009

Before the stretch: T.I. promised he would use his down time productively, telling MTV he would not “just be sitting still doing nothing” and that “while I’m there, I’ll be able to strategize my comeback.”

After the stretch: T.I.’s career took off while under house arrest in 2008, scoring numerous No. 1 singles from a chart-topping album written and recorded before and during the confinement, “Paper Trail.” As a free man, T.I.’s singles struggled to climb the charts, and in 2010 he was sentenced again for parole violations and served another 11-month stretch. While again incarcerated, his album “No Mercy” hit No. 4 despite being critically panned.

Ghostface Killah

Sentenced: Early 1999, for attempted robbery stemming from a 1995 charge, four to six months; entered prison later that year

Before the stretch: A member of the Wu-Tang Clan, Ghostface Killah had begun work on his second album when he had to take six months out for prison.

After the stretch: Upon release, Ghostface finished recording, and the resulting “Supreme Clientele” debuted at No. 7. The hurried follow-up, “Bulletproof Wallets,” however, tanked the following year.

Pimp C

Sentenced: January 2002, for probation violation related to an earlier assault charge, eight years; entered prison later that year

Before the stretch: A member of the rap group Underground Kingz, Pimp C had enough juice to generate a “Free Pimp C” campaign before entering prison. He had not released a solo album yet, though a collection of freestyles was issued while behind bars.

After the stretch: Six months after release in 2006, Pimp C’s debut, “Pimpalation,” hit the streets, and in 2007 UGK’s fifth, self-titled album hit No. 1. But late that year Pimp C was found dead of an overdose related to a breathing condition.