Just pulled up my list, I agree with 1990-1997, I have Big Pun for 1998 but DMX is also valid, I had Mos Def 1999, agree with everything 2000-2012 (thanks for also including Lupe), 2013 I had Drake but Rocky makes sense too, 2014 I had Freddie Gibbs but I'm biased, 2015 agree, 2016 as much as I hate to put Drake again I have him there right now mostly cuz I just haven't heard enough Chance, after that I have yet to really compile but I do have Future for 2024 no doubt
1979-1989 - Don't Know
1990 - Ice Cube
1991 - Q-Tip
1992 - Redman
1993 - Snoop Dogg
1994 - Nas
1995 - Biggie
1996 - 2Pac
1997 - Biggie
1998 - DMX
1999 - Dr Dre
2000 - Eminem
2001 - Jay-Z
2002 - Eminem
2003 - 50 Cent
2004 - MF Doom
2005 - Common
2006 - Lupe Fiasco
2007 - Ye
2008 - Wayne
2009 - Mos Def
2010 - Ye
2011 - A$AP Rocky
2012 - Drake
2013 - Kendrick
2014 - J. Cole
2015 - Kendrick
2016 - Chance
2017 - Kendrick
2018 - Pusha T
2019 - Tyler, The Creator
2020 - Freddie Gibbs
2021 - Tyler, The Creator
2022 - Kendrick
2023 - Travis Scott
2024 - Future
1990: Ice Cube
1991: Q-Tip
1992: Dr. Dre
1993: Snoop
1994: Nas
1995: Biggie
1996: Tupac
1997: Biggie
1998: DMX
1999: Jay-Z
2000: Eminem
2001: Jay-Z
2002: Eminem
2003: 50
2004: MF Doom
2005: Kanye
2006: Lupe Fiasco
2007: Kanye
2008: Wayne
2009: Jay-Z
2010: Kanye
2011: Drake
2012: Kendrick
2013: ASAP Rocky
2014: Cole
2015: Kendrick
2016: Chance
2017: Kendrick
2018: Pusha T
2019: Tyler
2020: Nas
2021: Tyler
2022: 21 Savage
2023: Travis
2024: Kendrick
2025: Kendrick (so far)