It’s not often that two of the biggest stars in their respective genres are cast opposite of each other in leading roles in a major motion picture film, but that is what occurred in 1993 when director John Singleton tapped Janet Jackson and Tupac Shakur to headline his romantic drama Poetic Justice. The follow-up to Singleton’s 1991 Oscar-nominated coming-of-age film Boyz n the Hood, Poetic Justice arrived at a time when movies centered around black love were plentiful, but set itself apart from the pack not only due to its sheer star power, but breakout performances from its supporting cast, which included Regina King, Joe Torry, and Tyra Ferrell.

Poetic Justice‘s lead character Justice (Janet Jackson), a hairstylist who is coping with witnessing the murder of her boyfriend, finds herself tagging along with her friend Iesha (Regina King), her boyfriend Chicago (Joe Torry) and his co-worker Lucky (Tupac Shakur) on a road trip to Oakland, but quickly runs into conflict when she and Lucky struggle to co-exist. Drama and romance ensues between all four parties, as they attempt to make it to their destination while tending to matters of the heart.

Released on July 23, 1993, Poetic Justice was a massive hit, debuting at No. 1 at the box office during its opening weekend and grossing over $27 million domestically, nearly doubling its $14 million budget. Jackson, who contributed the theme song “Again” to the soundtrack, would earn an Academy Award nomination for Best Original Song, as well the award for Best Female Performance at the MTV Awards, making it one of her more acclaimed performances as an actress.

In the wake of Poetic Justice‘s release, many of its stars would go on to reach even greater success in their respective careers, however, they will always be remembered for their roles in the film, which has gone on to become a timestamp for pop and urban culture in the 90s and continues to resonate with a new generation of fans more than two decades later. With today being the 25th anniversary of it hitting theaters, REVOLT thought it was only right to celebrate by sharing 10 reasons we feel Poetic Justice is an undisputed classic and one of the quintessential films of its era.

1 | Q-Tip’s cameo

During the early 90s, no movie targeting the urban community was complete without a cameo from a rap star. One artist that showed off their acting chops while getting air time on the big screen was A Tribe Called Quest member Q-Tip, who was cast in the role of Markell. The boyfriend of Janet Jackson’s character Justice, Markell would be shot at point-blank range while in the car with Justice after running into some rivals at a drive-thru movie during the opening minutes of the film, starting Poetic Justice off on a tragic note. In spite of his time on screen being brief, Q-Tip’s charm and charisma was evident, resulting in the Queens native appearing in a number of films over the years, most notably the 2001 film Prison Song, as well as Brown Sugar, She Hate Me, and Cadillac Records.

2 | Lucky and Tone Loc’s solidarity

Rapper Tone Loc appears in Poetic Justice as J Bone, a crack dealer who has fathered a child with the same woman as Lucky (Tupac Shakur). In spite of their disparaging digs towards one another, the two men have a mutual respect for one another, which becomes evident when Lucky gets into a fight with a man his baby mother is sleeping with while neglecting her children. After becoming aware of the altercation, J Bone completes a drug transaction in the middle of the commotion, but wastes no time jumping in and helping Lucky pummel his opponent with a barrage of punches, kicks and stomps. His presence in the film may have been marginal, but Tone Loc’s chemistry with Tupac during their scenes is electric and undeniable, making it one of the more memorable pairings of rappers on the big screen.

3 | Its poetic moments

Poetic Justice lives up to its name as Jackson’s character recites poems throughout, most notably “Alone” and “Phenomenal Woman” by famed poet Maya Angelou, who also makes an appearance in the film. Serving as the backdrop to some of the film’s most moving moments, “Alone” and “Phenomenal Woman” give Poetic Justice added character and substance, and helped introduce a generation to the greatness of Angelou.

4 | The road trip to Oakland

Nothing brings people together or tears them apart quite like a road trip, which we learned from watching Justice, Lucky, Chicago and Iesha’s experience. Over the course of the trip, all four characters experience a range of emotions and moments that will alter their lives forever and discover things about themselves that would impact their outlook on life. From shooting water pistols at the rest stop, to heated arguments and quickies in the back of the mail truck, Poetic Justice showed the good, bad and ugly of the co-ed road trip and romanticized the idea of mixing work with a little bit of pleasure.

5 | It taught us how to properly crash a cookout

One of the most endearing scenes from Poetic Justice occurs when Lucky, Justice, Iesha and Chicago stumble upon a cookout for a family reunion, which they join under the guise of being relatives of the family themselves. From Lucky ingratiating himself to cousin Pete, to Iesha and Chicago’s exchange with the matriarchs of the family, the family reunion is remembered as one of the key moments from the film and resonated with a nation of young, black partycrashers while proving that, at the end of it all, we’re all one big family.

6 | Regina King’s performance

After capturing the hearts of black America in her role as Brenda Jenkins on the sitcom 227 as a teenager, Regina King did what many other child actors have failed to do and successfully transitioned into adulthood, beginning with her movie debut in the 1991 John Singleton film Boyz n The Hood. However, two years later, Singleton cast King as Iesha in Poetic Justice, a role that would truly showcase her talents and ability to captivate an audience. The best friend of Justice and a borderline alcoholic, Iesha’s character is one that struck a chord with viewers in a big way and stole the show from both Tupac and Janet Jackson at times. From her scathing takedown of Chicago to her sisterhood with Justice, King’s portrayal of Iesha was one that solidified her as a viable supporting actress and stands as one of the breakout roles of her career.

7 | Chicago’s meltdown

Comedian Joe Torry first gained notoriety as one of the faces of Def Comedy Jam during the early 90s, but made another big splash with his role as Chicago. A coworker of Lucky and Iesha’s boyfriend, Chicago’s inflated sense of self and comedic one-liners initially make him a favorable character, however, his insecurity, coupled with Iesha’s apparent lack of respect for him, turns the mail truck into a powder keg which explodes and culminates in an act of domestic violence and creates division among himself and his partner-in-crime. Plus, Lucky throwing Chicago’s trusty brush into the canyon was one of the most hilarious, yet fitting moments in one of the best movies of the decade.

8 | The battle of the sexes

One constant theme throughout Poetic Justice was its commentary on the state of relations between men and women, with both sides weighing in on the issue. Moments like the infamous salon scene where Lucky first encounters Justice and her man-eating boss Jessie, and his intense arguments with Justice during their trek to Oakland are just a few of a handful of instances in Poetic Justice that tackle men and women’s gripes with one another and the disconnect that occurs at times within the black community as a result.

9 | It showed Tupac’s range as an actor

Wowing audiences with his portrayal of Bishop in the 1991 film Juice, Tupac Shakur was touted as an artist with the acting chops to thrive in Hollywood. However, being typecast into roles as a thug or criminal has stunted the careers of many actors, let along artists looking to make the transition into film. So when Tupac was cast as Lucky, a law-abiding mailman and caring father looking to help his cousin pursue their dream, the role was the polar opposite of Bishop and was a testament of his range as an actor and his ability to play characters that didn’t align with his image as a rapper.

10 | Janet Jackson’s show of strength and vulnerability

Long before feminism became a topic of discussion in the mainstream, Poetic Justice helped introduce a nation of black women to the movement through Jackson’s character Justice, who demanded respect from men like Lucky and helped uplift women like her friend Iesha and inspired them to love themselves. In addition to her strength and lack of tolerance for being objectified or called out of her name, Justice also displays a vulnerability that belies her hardened exterior, particular in her comfort of Lucky and their unlikely romance.

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