On August 25, 1999 the film In Too Deep hit theaters worldwide. This classic crime drama remains a gripping exploration of loyalty, morality, and the blurred lines between law enforcement and the criminal underworld. Directed by Michael Rymer, the film features an all-star cast, including Omar Epps, LL Cool J, Nia Long, Stanley Tucci, Hill Harper, Pam Grier, and more.
Epps and LL Cool J delivered standout performances as an undercover cop and a ruthless crime lord, respectively. Adding to the film’s legacy, its hip-hop-infused soundtrack, released by Columbia Records on August 24, 1999, peaked at No. 28 on the Billboard 200 and No. 8 on the Top R&B/Hip-Hop Albums chart. The soundtrack also marked the debut of 50 Cent with his single “How to Rob,” further cementing In Too Deep as a cultural touchstone in late ’90s cinema and music.
In celebration of the film’s 25th anniversary, let’s take a look at the cast of In Too Deep then and now.
In the film Epps portrayed an undercover cop who becomes dangerously immersed in the criminal underworld as J. Reid. His performance was a powerful depiction of the fine line between justice and corruption.
Prior to In Too Deep, Omar Epps had established himself as a staple in Black cinema. After shining in Juice, The Program, Major League II, and John Singleton’s Higher Learning. After the film, Epps had a longstanding role in House, as well as 2000’s Love & Basketball. He portrayed Malcolm on Power Book III: Raising Kanan for three seasons, and can be seen in the upcoming film The Deliverance.
LL Cool J took on the role of Dwayne Gittens, aka “God,” a feared crime lord. His portrayal of the menacing yet charismatic figure added depth to the film’s exploration of crime and morality.
Already an iconic hip-hop artist at the time In Too Deep was released, LL Cool J appeared in several films after 2003, including S.W.A.T. and Last Holiday, and has also been a cast member of NCIS: Los Angeles since 2009. At the time, he was still an active rapper, dropping four albums from 2004 – 2013.
Long played Myra, the love interest of J. Reid, who struggles with her partner’s dangerous double life. Her performance brought emotional complexity to the film.
Long has become synonymous with Black cinema. After starring in classics like Boyz N The Hood, Friday, and Love Jones, this actress created memorable moments for audiences worldwide, especially as Jordan Armstrong in The Best Man series. She also appeared in music videos for Dr. Dre, Ashanti, and Kanye West, as well winning an NAACP Image Award in 2004 and 2005 for her performance in Third Watch.
The supportive friend to Jeffrey Cole who adds a layer of tension and moral questioning to the narrative.
Harper has had a successful career in television, starring in CSI: NY and The Good Doctor. Beyond acting, he’s an author and motivational speaker, known for his activism in education, political advocacy, and financial literacy.
Pam Grier starred as Det. Angela Wilson, the tough, no-nonsense police officer who tries to keep Cole grounded in reality as he delves deeper into his undercover role.
Grier, an icon from her Coffy and Foxy Brown days, remains a beloved figure in cinema. She has appeared in shows like The L Word and films such as Just Wright. Her memoir Foxy: My Life in Three Acts offers insight into her legendary career.
Aunjanue portrayed Denise, a character intertwined in the dangerous world Cole navigates. Her role, though smaller, was impactful in grounding the story’s emotional stakes.
Ellis-Taylor has earned critical acclaim with roles in If Beale Street Could Talk, Lovecraft Country, and her Oscar-nominated performance in King Richard. She’s celebrated for her powerful on-screen presence and versatility.
Mýa appeared as Loretta, bringing a fresh energy to the film with her portrayal of a woman caught up in the criminal chaos.
Mýa continues to thrive as a singer, releasing albums independently and winning a Grammy for her album Smoove Jones. She also competed in Dancing with the Stars, where she showcased her dance talent.
Jermaine Dupri made a memorable appearance as Melvin, adding authenticity to the film’s portrayal of the urban music scene and street culture.
Dupri remains a powerhouse in the music industry, producing hits for artists like Usher, Mariah Carey, and Jay-Z. He’s also an inductee of the Songwriters Hall of Fame and continues to influence the industry as a producer and entrepreneur.
