To my own astonishment the legendary Ricky Walters b/k/a Slick Rick had never been featured in a “Top 10” on this website. I’ve been binging on old school rap classics lately, although I use the term “old school” with a sense of irony given that when Rick was in his prime we were calling Melle Mel and Kurtis Blow “old school.” These days I realize any rapper whose career started more than 30 years ago seems ancient by today’s standards, but when a young Doug E. Fresh and MC Ricky D dropped “La-Di-Da-Di” it was for me and many others a marker that set the two generations apart. It’s also the perfect place to start this list. There’s no official video for this classic single, but there’s a vintage live performance that’s just as good.

1.) Doug E. Fresh and MC Ricky D – “La-Di-Da-Di (Live)”
2.) Slick Rick – “Children’s Story”
3. Slick Rick – “I Shouldn’t Have Done It”
4.) Slick Rick – “Hey Young World”
5.) Doug E. Fresh & MC Ricky D – “The Show (Live)”
6.) Slick Rick – “Teenage Love”
7.) Slick Rick f/ OutKast – “Street Talkin'”
8.) Slick Rick – “Can’t Dance/Midas Touch”
9.) Slick Rick – “It’s a Boy”
10.) Slick Rick – “Sittin’ In My Car”