Comedy Clash: Watch Shaggy’s Hilarious Appearance on ‘Fallon’

In what easily qualifies as “the most dancehall moment” in any era of The Tonight Show—Carson, Leno or Fallon—Shaggy found himself in a deejay clash of sorts on last evening’s show. As Jimmy Fallon put the battle with announcer Steve Higgins, it was a “Shaggy Off, a rap battle to find out who’s the better Shaggy—Higgins, or Shaggy the rapper.” And what we thought might be a re-hashing of the old “square old white guy doing ‘It Wasn’t Me'” gag (Remember Mike Ford, the Bill Clinton lookalike from Late Night at the Apollo back in the day?) turned out to be something much better, right from the moment Shaggy introduced himself with the words: “large up.” After starting things off with some jokes, Mr. Boombastic even broke from comedy to offer a proper demonstration in Jamaican-style toasting, while The Roots’ Black Thought tossed out a capella airhorns.

This wasn’t the first time Shaggy and The Roots have connected in a hip-hop meets reggae style. We’d be remiss not to point you to our own “Caribbean segment” at the 2011 Okayplayer Holiday Jam, when Shaggy led an all-star bashment revue that also included appearances from Patra, Rayvon, Red Fox, Mr. Easy and master of ceremonies Rahzel, backed up by The Roots. Watch last night’s “Shaggy Off” and that original jam session, in all of its unedited glory, below: