Some mf'er asked, kinda, so: The History of Hip-Hop, 1985-2008. Twenty-four songs for twenty-four years. This is, intentionally, a very mainstream list, aiming for songs-of-the-year and legendary figures and broad trends and whatnot. Sorry I missed your favorite (I missed my favorite, too), but please feel free to argue with me.
1985: LL Cool J - Rock the Bells
1986: Run DMC - My Adidas
1987: Eric B & Rakim - I Know You Got Soul
1988: Marley Marl f. Masta Ace, Craig G, Kool G Rap and Big Daddy Kane - The Symphony
1989: Public Enemy - Fight the Power
1990: A Tribe Called Quest - Can I Kick It?
1991: Geto Boys - Mind Playing Tricks On Me
1992: Dr. Dre f. Snoop Doggy Dogg - Deep Cover
1993: Notorious BIG - Party and Bullshit
1994: Nas - It Ain't Hard to Tell
1995: Method Man f. Mary J Blige - I'll Be There For You/You're All I Need To Get By
1996: De La Soul - Stakes is High
1997: Company Flow - Fire in Which You Burn
1998: Big L - Ebonics
1999: dead prez - Hip-Hop
2000: Eminem - Stan
2001: Talib Kweli & DJ Hi-Tek - Expansion Outro/For Women
2002: Scarface - My Block
2003: Jay-Z - 99 Problems
2004: MF DOOM - Hoe Cakes
2005: Cassidy - I'm a Hustla
2006: Clipse - Mr. Me Too
2007: UGK - International Players Anthem
2008: Lil Wayne - A Milli