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.
21. Drake, Room for Improvement (2006)