When Reagan was in office, people called him the “Teflon president” because attacks against him had a way of not sticking. It’s one of the definitions of a successful president, that the opposition is flummoxed, it’s hard to carve out a coherent contra point of view that resonates with people. Reagan was hard to satirize because those who liked him, of whom there were many, just ignored or dismissed the satire. Similarly, President Obama has been difficult to lampoon; when he became president there was some talk among comedians to the effect that he was hard to make fun of—I haven’t seen much in the meantime to contradict this.
In any case, in the 1980s the idea of turning Reagan into a rapper was well-nigh irresistible. In 1982, perhaps predictably, Rich Little was first out of the gate with his “President’s Rap,” which featured no rap at all, merely a loooooong (9 minutes!) chunk of his Reagan schtick over a bed of Tom Tom Club’s “Genius of Love.” The song relates in some way to Saturday Night Live (although I could find no evidence that Little ever appeared on SNL)—at one point he has Reagan crying “Live, from New York, it’s Saturday Night!” and the song features a cameo by, of all possible personages, Mr. Bill, a plasticine axiom of the show’s Belushi years. You are encouraged to regard the use of Mr. Bill (not to mention Hervé Villechaize) as an index of how toothless these Reagan rap satires were.
In 1984 Air Force 1 threw together “See The Light, Feel The Heat,” which played a series of Reagan soundbites over some beats. Again, not a true rap—it’s all sampling.
In Reagan’s second term Ron & the D.C. Crew came out with “Ronnie’s Rap”—this is probably the best Reagan rap from a rapping perspective. The vocalist does a very nice job with the Reagan impression, and the lyrics are solid too:
Met with Gorbachev in ‘85
to talk about how everyone could stay alive.
And though he seemed to be a guy with class,
if he doesn’t play ball, we’ll nuke his ... country!
The only Reagan rap I could find with an actual video is unfortunately one about which I’m unclear on the details. On YouTube it’s identified merely as “Rappin’ Ron Reagan” and I don’t know who the artist is or what year it came out. In the video Reagan pops out of his presidential limo in the ghetto in the effort to “try to get those mothers to the polls,” if I understood that verse right. There’s some cringeworthy ebonics, the actor neither looks nor sounds particularly like Reagan, and yet I appreciate the effort. The satire, such as it is, is probably the most biting of the bunch, and the jokes are probably the strongest. Also it has breakdancing in it—“Don’t need cardboard for my shoulder spins”—actually, that very fact probably indicates that it’s pretty early, 1982 or 1983.
Most of the songs just love to include references to “Nancy” (his wife) and “Ed” (Meese, his attorney general)—even here we see why it was so difficult to make fun of Reagan. If you’re highlighting the fact that he dotes on his wife, you’ve probably lost the battle.