Somewhere Charles Hamilton must be thinking, Well, at least I’m not that guy. Once in a position to achieve crossover success, Yung Berg followed up his 2007 hit single “Sexy Lady” with four unfortunate episodes in 2008, listed below. Just when we thought the Chicago native’s luck had changed, following a quiet 2009, Berg’s history of defamation started up again this past March, when a former sex partner dissed him on Twitter. Since we here at XXL can’t decide which of the guy’s stories is the worst, it’s up to you, dear readers, to evaluate his track record. Revisit the scarred artist’s five most embarrassing moments here, and vote for the biggest failure. Grief counselors are standing by.

1. July 2008—Dark-Skinned Disrespect: While being interviewed on Shade 45’s Lip Service, Berg admits that he’s “kinda racist” and doesn’t “like dark butts too much.” To be more precise, he prefers ladies whose skin color is “no darker” than his own. Angering your female demographic is never smart business for a young LL Cool J type.

2. August 2008—The Chain Snatching: Berg, scheduled to headline Detroit radio station Hot 102.7’s Summer Jamz, misses the performance after being beat down the night before outside of local nightclub Plan B. In the midst of the scuffle, his gaudy Transformers neck piece is stolen. Where’s Optimus Prime when you need him?

3. October 2008—Maino’s Unholy Act: Brooklyn’s own Maino goes public with news that he smacked Yung Berg in an Atlanta nightclub. Berg’s “disrespectful” ways, he says, led the BK native to do “God’s work.” Not even a thug’s prayer could salvage Berg’s street credibility.

4. October 2008—The R&B Beef: As a guest on Power 106’s Big Boy’s Neighborhood, in Los Angeles, Ne-Yo is asked which artist he’d like to serve with a “three-finger slap.” His victim of choice? Yung Berg, of course, for “not tryin’ to do nothin’ original.” Beware the wrath of a lover turned fighter.

5. March 2010—The Scorned Video Model: Part of a sex tape starring Yung Berg is leaked online by Jenna Shea, an old Eye Candy–like jump-off of his pissed over an unpaid YB music-video appearance. She then tells her Twitter followers that she’s seen Berg get “robbed” and “pistol-whipped” and that he was “cryin’.” At this point, who could blame him?