#5 - Gay Ray, the Reggae Gay [Explicit]
The quote that introduces this clip over at Funny or Die says it all: “I’m simultaneously an offensive homophobic cliche and a culturally-insensitive stereotype.” Gay Ray washes his dreadlocks with Paul Mitchell tea tree lemon sage conditioner and proclaims, “It’s always been mi dream to fuse dancehall skanking with the choreography of Bob Fosse.”
#4 - Craig “Leftside” Parkes, “I Love Breast”
Not totally fake reggae since Leftside is an authentic dancehall star but his going Weird Al on his bashment colleague Vegas was too good to pass up. Minus points for not actually shooting a video—this could have been top ranked if he did a full on production. But even a camera-phone skit like his for-insiders-only Sharon Burke impression, Leftside’s humor is always dead-on.
#3 - Cedric the Entertainer Presents, “Rasta Tom”
Toting an extra-large Glad bag full of weed onstage and fulfilling all the usual reggae-singer stereotypes, this one-off character from Cedric’s short-lived Fox sketch comedy show takes an unpredictable turn when he starts singing about his “White Woman Queen.” It only gets worse from there. “If you like sellout music, then come with me, come again.”
#2 - Eddie Murphy on Saturday Night Live, “Kill the White People
He thought they were going to sing “Day-O.” The original and gold standard of joke reggae songs. We could talk about the levels of genius in this skit all day long but it comes down to two big factors. 1) like most of Eddie’s musical impressions (Little Richard, James Brown, Jesse Jackson singing “Heimytown”) from the salad days, it actually works as music and the more retardedly simple they try to make it sound, the better it is. 2) it’s funny because it’s true.
#1 - Marlon Wayans on In Living Color, “Mr. Ugly Man”
As funny as In Living Color‘s Carrey-as-Snow skit was, this gem (from the classic LP “Rough & Ugly Vol. 1″) is the most memorable and oft-cited dancehall-themed clip from every Jamerican’s favorite—or least favorite—’90s TV show. An egalitarian Marlon Wayans even let T’Keyah Crystal Kemah get some of the choice lines: “Champion lover, don’t come home tonight/Ugly brother, if you do don’t turn on the lights.”