Song: "The Watcher" (1999)
Album: 2001

How does one of the originators of the original gangster rap group enter his third decade in the rap game after a not-insignificant absence? Ask Dre, who took to his mid-life crisis with grace, coming across as a veteran adjusting to the rapidly changing tides of both his life and rap, with a weirdly abstract existential anxiety slowly forming some kind of acceptance. If you're gonna age—and if you're going to be one of the first great rappers to attempt career success at a late age, and find it—you should probably do it with some level of self-awareness. Dre did it from the start, and separated himself from every other rapper that's going to get old and try rapping in the process.