While the hip-hop love song isn’t so much of a rarity these days, there were only a handful back when Slick Rick’s “Teenage Love” came out at the end of ’88. Most rappers weren’t going anywhere near slow jams for fear of being seen as soft and losing their street credibility. Even after LL Cool J hit with “I Need Love” back in ’87, it was at the expense of his “hard” image-at least until Mama Said Knock You Out restored his badass image in the eyes of the (then) largely male and urban (urban as in city-dwelling, not urban as a substitute word for black) rap audience.

Very interesting, then, that Slick Rick chose the ballad “Teenage Love” as his debut solo single. He initially made a name for himself as a member of Doug E. Fresh’s Get Fresh Crew, scoring a quick classic with the legendary 12″ single “The Show/La Di Da Di” (two songs that got sung/rapped/chanted on the school bus DAILY). Three years passed between those hits and the release of his debut album The Great Adventures of Slick Rick-an eternity back in those days of hip-hop infancy. Rick left The Get Fresh Crew and got swagger-jacked by former classmate Dana Dane (who rode Rick’s style and British lilt all the way to Platinum sales), but that time away helped create a classic: Great Adventures is a five-star effort and it announced Rick as a first-class storyteller. “Teenage Love” (a song significantly more mature than it’s title indicates) was just one great narrative on an album full of them, from the cautionary tale “Children’s Story” to the hilarious “Indian Girl”, a song so politically incorrect it probably wouldn’t even be released these days.

Anyhow, if you don’t know the rest of the story, Great Adventures (in part due to the success of “Teenage Love”) was a runaway success, but Rick’s career was soon derailed due to ongoing legal problems stemming from an incident that eerily mirrors the lyrics of his own “Children’s Story”. He shot and wounded his cousin and then embarked on a high speed chase to elude police. He would up imprisoned for several years, and has faced the threat of deportation several times before receiving a full pardon recently. Rick (the only person in the free world who can still wear tons of jewelry and not look like a complete idiot) hasn’t recorded new material in a decade, but his status as hip-hop royalty is unquestionable.

…and check out the Big Daddy Kane cameo in this video!