Label: Gangland/Def Jam Records
Worst Song: "Jimmy Choo" f/ Ashanti


Shyne was serving a 10-year prison sentence when Def Jam decided to sign him to a seven-figure recording contract in 2004. Honestly, Shyne should have gotten another five years for highway robbery after he signed that deal. GBA was a publicity stunt that worked for a minute—it peaked at No. 3 on the Billboard 200 chart—but was ultimately a record made up of leftover songs recorded prior to Shyne's jail stint.

At the time we figured Shyne's deal was the worst million dollars that Def Jam had ever spent. That is, until last year when Shyne got out of prison, released some of the worst music we've ever heard, and then signed another multi-million dollar deal with Def Jam. Yo L.A. Reid, WTF?!