“Girl, don’t you know that the world is just a big place for us to go out and fuck up in it?”

With Boyz n the Hood already under his belt, wonderkid John Singleton was still only 24 years old when he wrote and directed this nuanced romantic drama about the relationship and creative struggles of a young hairdresser (played by Janet Jackson, sporting her now-iconic braids). Tupac Shakur co-stars as a troubled USPS driver who takes Jackson and their friends on a drama-fueled road trip through California. Jackson and Shakur were at the height of their fame when the film came out, and their chemistry lights up the screen all the way from South Central LA to Oakland. Co-starring scene-stealer Regina King with cameos by the likes of Q-Tip, Tone Loc, Maya Angelou, and the true originators of rap, The Last Poets.

Ayana Contreras is Content Director of Vocalo. She is an avid collector of vintage vinyl records, and shares her knowledge as host of Reclaimed Soul on both Vocalo and WBEZ. As a DJ, she has shared the stage with a variety of artists, from Roy Ayers to Gang of Four.