- The single "P.S.K. (What Does It Mean?)" was the first Gangsta Rap track, as the song loosely alluded to the gang Park Side Killas. Ice-T admitted that this was his inspiration to rap about his own gang experiences.
- His collaborations with independent film director Abel Ferrara, who used Schoolly D songs in quite a few of his movies, including King of New York and Bad Lieutenant, as well as letting Schoolly D score his movie R Xmas. He even has a feature especially devoted to him on the DVD release of King of New York.
- His song "Signifying Rapper" was the result of a lawsuit due to the fact that it was based around the Led Zeppelin song "Kashmir". The rock band didn't even notice until the song was featured in Bad Lieutenant.
- Aqua Teen Hunger Force featured him as a narrator and music creator.
His career has produced many notable albums and classic Hip-Hop tracks.
- Schoolly D (1985)
- Saturday Night! The Album (1987)
- Smoke Some Kill (1988)
- Am I Black Enough for You? (1989)
- How a Black Man Feels (1991)
- Welcome to America (1994)
- Reservoir Dog (1995)
- Funk 'N Pussy (2000)
- International Supersport (2010)
Tropes associated with Schoolly D and his works include:
- All Men Are Perverts: Comes up a bit. In "No Good Nigga", he brags that he'll "fuck you if you're green", if you bring him home to her mother, he'll have sex with her, too, and even says "I might fuck your cat".
- All Women Are Lustful: "Mr. Big Dick"
- But Not Too Black: Subverted with "Am I Black Enough For You?"
- Gangsta Rap: Ur-Example. "P.S.K. (What Does It Mean?)" was specifically cited by Ice-T as the first Gangsta Rap song.
- Long Song, Short Scene: The version of "Am I Black Enough For You?" heard in King of New York has a different beat from the album version. It was never released in any form outside of this movie. Most people loading up the album version on YouTube expect to hear the version from the movie.
- Rap Rock: "Signifying Rapper", despite the same album's anti-rock, pro-rap stance.
- Two-Faced Aside: Smoke Some Kill contains two tracks devoted to bashing rock music. On the same album as "Signifying Rapper", a guitar-fueled takeoff of "Kashmir".
- Jimmy Page sued Schoolly D for using "Kashmir" in "Signifying Rapper", yet Page and Tom Morello played the exact same riffs in Puff Daddy's 1998 Godzilla single "Come with Me", opening a huge amount of criticism. Abel Ferrara in particular slammed Page, since removing "Signifying Rapper" from Bad Lieutenant ruined the movie in Ferrara's view. Not to mention, Led Zeppelin was really guilty of plagiarisms in their early days, having been hit with similiar lawsuits for taking riffs and lyrics from blues bands and not crediting them. Thus, their lawsuit against "Signifying Rapper" is really not justified.