When it comes to the battle of great rappers of the ’90s, I don’t like to take sides in the Biggie vs. Tupac argument. As a West Coaster, I grew up being much more familiar with Tupac’s music, but can certainly appreciate Notorious B.I.G.

A couple weeks ago, I saw an amazing documentary called Bastards of the Party. The documentary, directed by Cle Shaheed Sloan, focused on the beginnings of the gang wars in California, tracing it back to the Black Panthers and beyond. Sloan appeared as an actor in The Replacements, Training Day and Tears of the Sun, but is also known for being an inactive member of the Bloods. At the end of the documentary, there’s a long memorial for all of the members of the gang community that Sloan knew who had died. While the names, pictures and dates of the many men who have passed scroll by, Tupac’s “So Many Tears” provides a fitting message, but also a compelling one.

The combination of Bastards of the Party and “So Many Tears” provided another interesting contrast, because while Sloan argued that it is indeed possible to walk away from one of these gangs, Tupac constantly sings of being stuck. But one of the things I’ve always appreciated about Tupac is his constant questioning of what he’s doing, knowing it’s wrong, but explaining his actions by showing the hand he was dealt, and constantly juxtaposing the two. In “So Many Tears,” he sings in the first verse – “call on the sirens, seen him murdered in the streets, is there a heaven for a G?” then he goes on to sing about his certainty of his own death, yet also his remorse and his anger.

While he certainly suffered from a less glossy production than Biggie, it’s songs like this that make me appreciate Tupac’s introspection. Though he’s singing about a very small world, his themes of being cursed, stuck, and angry with oneself are ones that apply to many of us.

Tupac: “So Many Tears” (download)