Okay, sorry for overloading this thread with the book, but I'll list Shea's picks from some years and my quick thoughts on them
2003- "In Da Club" by 50 Cent
I thought, other than "Rapper's Delight" in 1979, this was the easiest pick of any. I mean, we can argue about 50 Cent's actual talent, but there is no doubt 2003 was his year and incredibly important.
2010- "Monster" by Kanye West, Rick Ross, Jay-Z, Nicki Minaj
He picked this mostly for what it did for Nicki Minaj, but since Nicki Minaj is a pop star and not a rapper, I felt like (I can't believe I'm going to say this) Wiz Khalifa's "Black and Yellow" was the song for what it for the laid back rap era that we are slowly phasing out from now. Honestly, there were good songs but not any incredibly important ones. This was a tough one to go through.
1994- "Juicy" by Notorious B.I.G.
Juicy is a great song. It's a very significant song. It put Biggie on the map. It's an MVP worthy song. It's not "NY State of Mind" by Nas. Not even close.
2001- "Takeover" by Jay-Z and "Ether" by Nas
He kind of cheated because he chose two songs and it makes sense considering how big this beef was so I didn't have a problem with how he broke it down. If I had to choose one song, I'd probably go with Move, ***** by Ludacris because that song basically put him on the map and along with Ms. Jackson (released in late 2000 by OutKast) made Atlanta rap.
2002- "Grindin" by Clipse
This was ridiculously hard. So you have "Grindin" by Clipse. You have "Lose Yourself" by Eminem. "Hot in Here" by Nelly. Hell, you could make a case for "Always on Time" by Ja Rule, "03' Bonnie and Clyde" with Jay-Z and Beyonce, or "Get Low" by Lil Jon and the Eastside Boys". Dear God, how do you pick that?