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10 Terrible Financial Choices in Music History

7. Jay-Z and R. Kelly's worlds collide
As noted earlier, Jay-Z doesn't make bad businesses decisions often, and -- at the time -- this seemed like a no-brainer. He had just wrapped up a radio-fueled feud with Nas that is now the stuff of hip-hop legend, his album The Blueprint just went double platinum and produced his highest-charting song to date -- the party anthem Izzo (H.O.V.A). Its follow-up pulled off the same sales feat while giving him the biggest commercial success of his career thus far with help from future wife Beyonce Knowles on '03 Bonnie and Clyde.

R. Kelly, meanwhile, had just worked with Jay-Z on the tracks Guilty 'Til Proven Innocent and Fiesta, just had a hit single with The World's Greatest from the movie Ali and was putting the finishing touches on his highly successful Chocolate Factory album and hits such as Step In The Name of Love, Ignition and Snake. On paper, a collaboration album and tour seemed like a great idea. Certain realities made it less than ideal.

In February 2002, a videotape surfaced of R. Kelly allegedly having sex with and urinating on a 14-year-old girl. As R. Kelly and Jay-Z's album Best of Both Worlds hit stores, cops were searching Kelly's Florida home for evidence. Kelly was indicted on child pornography charges and arrested in January 2003. The album's tour was postponed until 2004, but even that couldn't save the enterprise as friction between R. Kelly and Jay-Z came to a boil during a performance at Madison Square Garden (MSG) when R. Kelly quit the show, claiming two members of the audience flashed guns at him. Saying Kelly had held up the show for much of the tour and tested his patience for the last time, Jay-Z kicked Kelly off of the bill and completed the final leg with a "Jay-Z & Friends" lineup.

Though Jay-Z and R. Kelly both recovered nicely -- with Jay-Z's album sales and business ventures flourishing and R. Kelly being acquitted of all charges in 2008 -- the tour was an unmitigated disaster and Best of Both Worlds' 1 million in U.S. sales (or 500,000 per headliner) was a professional low for all parties involved.

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