21. Drake, Room for Improvement (2006)
The title of Drake's debut mixtape is remarkably prescient. The Toronto superstar-to-be was already showing a ton of talent and promise, but he hadn't yet discovered many of the future trademarks that made him stand out on future projects: Minimalist, ambient production, surprisingly introspective lyrics and, of course, post-808s and Heartbreak auto-tuned crooning. Six years later, Drake's certainly improved everything, from his mic skills, to his arm candy (hi, Rihanna), to the number of zeros in his bank account.