When Keeping It Real Goes Wrong: Acoustic Edition

Dave Chapelle teaches us that the art of "keeping it real" may sometimes go awry. According to urbandictionary.com, this occurs when "in the act of keeping it real, the outcome is unexpected and usually has a negative effect on the individual who decided to keep it real."

Singer-songwriters are not immune from this phenomenon.

When Keeping It Real Goes Wrong: Acoustic Edition
Photo illustration by John Seaborn Gray

1. John Mayer's Confederate Flag-Toting Wiener: Did you know that John Mayer's dick auditioned for the lead role in American History X? Just kidding, but by his own account, it would don a Klan hood if it could.

In a Playboy interview this year, Mayer was asked if black women have ever "thrown" themselves at him. He responded by saying: "My dick is sort of like a white supremacist. I've got a Benetton heart and a fuckin' David Duke cock. I'm going to start dating separately from my dick." Umm. Gross. And offensive.

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After an onslaught of backlash from the likes of Talib Kweli, Margaret Cho and Ice-T, Mayer apologized for his statements on Twitter. Just when we started to think you were kind of cool for your spot on Dave Chappelle's "White People Dancing" skit, it turns out your wiener wanted to lynch him.

2. Lauryn Hill Cries... A Lot: Lauryn Hill's meteoric rise off the success of 1997's The Miseducation of Lauryn Hill - undeniably one of the most important albums of the '90s, and probably of all time - culminated in 10 Grammy Award nominations and solidified her place as a voice of the burgeoning neo-soul movement and of a generation. All at the tender age of 23.

When Keeping It Real Goes Wrong: Acoustic Edition

Post-Miseducation, Lauryn threw herself into self-imposed banishment, spurning a controlling label and the demands of living up to her public persona. She resurfaced in 2001 for a taped performance for MTV Unplugged 2.0 before a small studio audience, performing 13 new compositions.

The performance was marked by her frequent asides to the audience on the pressures of fame and her time soul-searching. She openly cried on a couple of occasions when speaking on her husband and children. Critics were divided on the performance. USA Today gave it 3 and a half out of 4 stars. But Rolling Stone called it "a public breakdown."

We personally think the critics were a bit rough on Lauryn. Why don't y'all try going from "that one chick in the Fugees" to one of the most gifted artists of a generation seemingly overnight?

Please come back, Lauryn. We miss you.

3. The MTV Unplugged That Almost Wasn't: The 1989 debut of MTV's Unplugged almost didn't happen thanks to the members of Squeeze who clearly didn't quite get the memo. On the day of the premier, frontmen Chris Difford and Glen Tilbrook showed up with electric guitars.

Producer Alex Coletti said: "Very funny, guys. Where are the acoustics? It's unplugged." Difford and Tilbrook looked at each other dumbfounded. Luckily the entire crew's scramble around town turned up a couple of acoustic guitars. Reading apparently isn't Squeeze's strong suit.

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