"Rappin' Duke"'s lyrics parody the hip hop bragging style popular at the time, wherein the rapper boasts of his/her seniority and superior rhymes and flow in his/her performance: "So ya think you're bad with your rap? / Well I'll tell ya, pilgrim, I started the crap. / When you were in diapers and wetting the sheets, / I was at the Ponderosa, rappin' to the beat." The lyrics also reference The Beverly Hillbillies TV theme song "The Ballad of Jed Clampett," with the words "Santa Barbara, that is / Swimmin' pools and movie stars," while also alluding to Ronald Reagan's presidency. (The acting careers of Wayne and Reagan overlapped for many years.) The song's constant refrain is "dah-ha, dah-ha," a parody of Wayne's distinctive laughter, sung to the music's slow beat.
The song uses the hip hop vernacular to make numerous pop cultural references from contemporary hip hop musicians such as Kurtis Blow and Run-DMC, to parodying the opening of Chaka Khan's 1984 hit "I Feel for You." "Rappin' Duke" was widely played in 1985, peaking at 73 on the 1985 Hot R&B/Hip-Hop Songs Billboard chart; and also charting on the Hot Dance Music/Maxi-Singles Sales for 1985. The song's success led to Brown opening in 1985 and 1986 for such artists as Bobby Brown and Stevie Wonder.
Brown signed with Tommy Boy Records after the album ¿Que Pasa? ran its course on the charts.
The video opens with an African-American cowboy alternately walking and back-sliding onscreen with a boombox propped on his shoulder, obscuring his face. He is replaced by various images from old cowboy movies: gun battles, rope tricks, and the like, as well as other assorted images vaguely connected with the song lyrics. Halfway through the song, the cowboy — his features always hidden — reappears poolside, together with a trio of swimsuit-clad women. He shows them a few tricks, including moonwalking in his cowboy boots, and then ends up in the pool with the girls. The video fades out with the cowboy staggering into the sunset.