The Monster Single of the Year award was first introduced to the MTV Music Video Awards in 2007, as they were revamped that year and a few new awards were introduced. When the VMAs returned to their old format in 2008, though, this award was not brought back.
| Year | Winner | Nominees |
|---|---|---|
| 2007 | Rihanna (featuring Jay-Z) — "Umbrella" |
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