Christmas Rappin' by Kurtis Blow: Download
This was the first Hip-Hop song released on a major label. Kurtis recorded this with the help of producers Robert Ford and J.B. Moore. They took it to Mercury Records, who signed Kurtis to a 2-single deal, under the condition that If both singles were successful, he would get an album deal. This was the first single, and it did very well. The second single was "The Breaks," and it became the first rap song to be certified as a gold record, selling over 500,000 copies. Kurtis got the album deal and became the first rapper signed to a major label.
Christmas in Hollis by Run DMC: Download
It's hard to believe Run DMC's "Christmas in Hollis" came out 20 years ago. The song was included on the 1987 A Very Special Christmas album, the first in a series of compilations to benefit the Special Olympics.
Millie Pulled a Pistol on Santa by De La Soul: Download
Great rap single from 1991 with a message that definitely clashes with the season. Millie is the daughter of the singer's social worker, suffering sexual abuse at her father's hands. Dad has a side gig as a Macy's Santa; you can see where this is going. Powerful stuff, but you might not want to hoist eggnog toasts while it's playing.
Santa's Rap Party by Super Jay: Download
For Y'all Disco heads, here's an underground pearl...courtesy of Peter Brown. He first came to fame with the first million-selling 12" dance single, "Do Ya Wanna Get Funky With Me." Brown was a pioneer in home recording, having recorded his seminal hit in his bedroom. (His '70s-era home recording studio is pictured on the cover of Westside/DNA's Get Funky With Me: The Best of the TK Years.) He also co-wrote Madonna's 1985 pop hit, "Material Girl,". Not too bad huh.