2Pac may have been a gangsta, but he had feelings too! This is a feminist anthem from Pac, with references to pro-choice politics and what one might call “rape culture”.

In a 1995 interview with LA Times journalist Chuck Philips, Tupac said:

I think the shit that I say, no one else says. Who was writing about Black women before ‘Keep Ya Head Up?’ Now everybody got a song about Black women. Who was writing about that when I was writing about that? Who was writing about their own problems? I wasn’t talking [blah blah blah], I was talking my real problems. I was really having problems with police. I was really having problems with life and just being Black and why the hell we gotta get stepped on so much? But then I’m making it, I thought I was successful when I’m still getting stepped on. How come I got a boot-print on my back and I’m successful? I just couldn’t believe that. So instead of me just bugging out and doing a post office move and just shooting everything up and going to jail for a million years, I just said, ‘Fuck it. I’m in here rapping. Why not just rap about some shit that’s really happening?’

The music video opens with an image about being dedicated to Latasha Harlins.

There are two follow-ups to this song, “Baby Don’t Cry (Keep Ya Head Up II)” and “Win (Keep Ya Head up Pt.3)” by E.D.I. Mean who is a member of 2Pac’s Outlawz.