And the award for worst pairing goes to...

The Video Music Awards have always been known to put together truly odd pairs of celebrities, case in point the infamous due of drag queen <a class="taxInlineTagLink" id="PECLB003589" title="RuPaul" href="/topic/entertainment/rupaul-PECLB003589.topic">RuPaul</a> and the aging comic legend  Milton Berle.This year, like every year, there were the good (<a class="taxInlineTagLink" id="PECLB001576" title="Eminem" href="/topic/entertainment/music/eminem-PECLB001576.topic">Eminem</a> and Tracy Morgan), the indifferent (Ne-Yo and <a class="taxInlineTagLink" id="PECLB005282" title="Chace Crawford" href="/topic/entertainment/chace-crawford-PECLB005282.topic">Chace Crawford</a>) and the painful (<a class="taxInlineTagLink" id="PECLB000528" title="Jack Black" href="/topic/entertainment/jack-black-PECLB000528.topic">Jack Black</a> and <a class="taxInlineTagLink" id="PECLB005362" title="Leighton Meester" href="/topic/entertainment/television/leighton-meester-PECLB005362.topic">Leighton Meester</a>). The two only received a pity chuckle or two from the crowd, and considering Jack Black's unexplained outfit, that was being kind.
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( Christopher Polk / Getty Images )

The Video Music Awards have always been known to put together truly odd pairs of celebrities, case in point the infamous due of drag queen RuPaul and the aging comic legend Milton Berle.This year, like every year, there were the good (Eminem and Tracy Morgan), the indifferent (Ne-Yo and Chace Crawford) and the painful (Jack Black and Leighton Meester). The two only received a pity chuckle or two from the crowd, and considering Jack Black's unexplained outfit, that was being kind.

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