FORTUNE — Ben Horowitz grew up listening to hip-hop and to this day remains an unabashed fan. It’s the music that he listens to, what’s in his head a lot of the time and what often inspires him to write some management lessons on his blog. Horowitz, who has become friends with some of hip-hop’s biggest stars, also believes there is a connection between rappers, who had to overcome obstacles and bootstrap their careers, and entrepreneurs.
At Fortune’s request, he created a playlist of his all-time favorite hip-hop songs, and you can read annotations of these classics over at Rap Genius, a site Andreessen Horowitz invested $15 million in.
MORE: Ben Horowitz: Silicon Valley’s stealth power
“Juicy,” The Notorious B.I.G. (Annotated lyrics)
“I Ain’t No Joke,” Eric B. and Rakim (Annotated lyrics)
“Rebel Without a Pause,” Public Enemy (Annotated lyrics)
“The Message,” Nas (Annotated lyrics)
MORE: Q&A with Nas: The rapper and the venture capitalist
http://www.youtube.com/watch?v=ws3Ks0FGxYM
“Can’t Tell Me Nothing,” Kanye West (Annotated lyrics)
“Let Me Ride,” Dr. Dre (Annotated lyrics)
“Mind Playing Tricks on Me,” Geto Boys (Annotated lyrics)
http://www.youtube.com/watch?v=-M8GszEN9MM
“A Week Ago,” Jay-Z (Annotated lyrics)
“Swiss Francs,” Ryan Leslie (Annotated lyrics)
“Keep Ya Head Up,” 2Pac Shakur (Annotated lyrics)
http://www.youtube.com/watch?v=cPx87Z6zHRQ