- Breakthrough Hit: "Bump n' Grind".
- Chart Displacement: He had two #1 singles. Surely they were "I Believe I Can Fly" and "Ignition", right? They were actually the still remembered "Bump n' Grind" and the long-forgotten "I'm Your Angel" (featuring Céline Dion).
- Follow the Leader: He is sometimes accused of sounding like Aaron Hall. Also, "Gotham City" was a rather blatant attempt at recapturing the success of "Kiss From a Rose" from Batman Forever.
- Role-Ending Misdemeanor: The sexual misconduct cases he accumulated over the course of a decade came back to bite him in the ass in May 2018 when Spotify stopped promoting his music in accordance with their policy on "hate content and hateful conduct", although the music was still available on the service. Then, in the first week of January 2019, the six-part miniseries Surviving R. Kelly was released, going into even greater detail about Kelly's sexual misconduct than anything before it, which culminated in a series of more recent revelationsincluding at least one comparing him to Ramón Rojo from A Fistful of Dollars in all but name (for context, such revelations detail how he coerced women to live with him and separated them from their families). Soon, Kelly became the subject of a criminal investigation in Georgia, an arrest warrant was put out for his manager, Kelly was dropped by RCA Records, and numerous prominent people, including Chance the Rapper and Lady Gaga, publicly regretted ever working with him. By February, Kelly's lawyer had turned himself in, and Kelly himself was charged with ten counts of sexual abuse, all but one of which involved underage girls; at this point, it appears to be less a question of if his career is over than a question of when.
- What Could Have Been: He was supposed to collaborate with Tupac Shakur on The Best of Both Worlds.
Trivia / R. Kelly