Label: 1017 Brick Squad/Asylum/Warner Bros.
Saving grace: "What It's Gonna Be"
Clunker: "Gucci Time"
From 2007's Back to the Traphouse through 2009's The State Vs. Radric Davis, Gucci built a phenomenal grassroots buzz. He seemed at the verge of crossing over; a few poor decisions were made, both on the part of his label (the Usher-assisted "Spotlight" was not the wisest single) and on his own (his inability to stay out of prison). But when he emerged for his next album, 2010's The Appeal: Georgia's Most Wanted, the public seemed ready to give him another chance. He had a huge budget. What could go wrong?

Everything. "Sold 60,000 the first week, second-best selling album I ever had," he told us. "But I didn’t push it or promote it or push the right songs, things got leaked." The lead single, the Swizz Beatz-produced "Gucci Time," seemed to misunderstand his appeal (pun unintended) completely, trying to wed his Southern style to an "On to the Next One"-style East Coast banger. It couldn't even get on the Hot 100, where his previous album had placed three singles.

Meanwhile, radio stations in other cities were still spinning mixtape tracks like "Beat It Up." His label, attempting to force his record across the counters, pulled his mixtapes from free tape sites like DatPiff. Collaborations with artists like Ray J and Wyclef Jean felt more than a little tone-deaf. Despite some highlights, The Appeal marked the moment when Gucci became consigned to the underground eternally. By the next winter, he released his collaboration with V-Nasty, BAYTL, and dreams of Lil Wayne-level pop superstardom were put to bed. —David Drake