A Brief History of "Weird Al" and Rhyme

Volcano Records
"Weird Al" the G.O.A.T.
This week sees the release of Mandatory Fun, the 14th studio album from the high priest of parody "Weird Al" Yankovic. Yankovic's uncanny ability to mimic and mock the stylings of his targets are always impressive, especially his endeavors into the world of hip-hop. While "Amish Paradise" and "White and Nerdy" are two of his biggest hits, Al's hip-hop history runs deep. Here's our complete history of "Weird Al's" hip-hop endeavors.

See also: The 10 Best Male Rappers of All Time

"Twister" 1988
While not a direct parody of a specific song, Al's also known for doing specific style parodies of certain artists. His first effort to rap on wax saw his take on Licensed to Ill-era Beastie Boys with "Twister." The penultimate song on Even Worse, it's largely forgotten in wake of that album's much more notable hits.

"Isle Thing" 1989
The third single from the soundtrack to his cult classic motion picture UHF, "Weird" Al's first official parody of a rap song came from Tone Loc's "Wild Thing." Rewritten about "Gilligan's Island," "Isle Thing" become one of the many Yankovic songs about television, a subject almost as near and dear to his heart as food.

"I Can't Watch This" "Taco Grande" 1992
Speaking of television and food, they became the subject of the two parodies on Al's next album 1992's Off the Deep End. Parodying MC Hammer's "U Can't Touch This" ("I Can't Watch This") and Gerado's "Rico Suave" ("Taco Grande") the hip-hop influence on the early 90s was evident, as also heard from the inclusion of Digital Underground's "Humpty Dance" and Vanilla Ice's "Ice Ice Baby" in the album's "Polka Your Eyes Out" medley.

"Amish Paradise" 1996
One of the biggest hits of Al's career came from his 1996 parody of Coolio's "Gangsta Paradise" with his song "Amish Paradise." While Coolio famously took issue with the parody, leading to Al now making sure he has permission from the artists themselves, they've allegedly since mended the fences. Fool.

"It's All About the Pentiums" 1999
One of Al's most ambitious videos came from his take on the rock remix of Puff Daddy and the Family's "It's All About the Benjamins" off of Running With Scissors. The very 1999 "It's All About the Pentiums" featured send-ups of numerous Bad Boy-era videos and boasted cameos from Drew Carey (playing his best Ma$e) and Emo Philips. The second single from Running With Scissors, the album also featured Pras' "Ghetto Superstar" and Beastie Boys' "Intergalactic" worked into the "Polka Power" medley.

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