In his big screen debut, DMX showed that he was a star on the rise in the Hype Williams-directed crime thriller Belly. Co-starring with Nas, Belly follows the different paths that the two drug dealers take. While Belly didn’t make a big splash at the theatres, with X’s electric performance as Tommy Bunz, the film became a cult classic.

Co-starring with Aalyiah and Jet-Li, Romeo Must Die, was a crime drama about a Chinese former police officer traveling to the United States in order to avenge his brother's death and his with the underground crime world. Romeo Must Die was a blockbuster hit grossing over 91 million dollars at the box office and establishing X as a force to be reckoned on the big screen.

Arguably one of the best Hip Hop documentaries of all time, Backstage gave a behind-the-scenes look at the 1999 Hard Knock Life Tour. Starring Hip Hop giants DMX, JAY-Z, Method Man, and Redman, Backstage featured live performances by several members of Def Jam's roster and gave an in-depth look at what really happens on tour. Plus, we got to see a freestyle between DMX and JAY-Z.

In the year 2000, DMX was the hottest rapper on the scene. He was everywhere including making T.V. appearances. On episode 18 of season 5 of Moesha, starring Brandy, X rips that stage with a live performance of “DMX (What’s My Name)” while the crew is on spring break.

From rhyming to acting in big-budget films, DMX could do it all. He even showed he could do live comedy by appearing on Mad TV. In this hilarious skit, X seeks advice on how to treat his woman from his mother, played by Aries Spears, who’s doing an impression on X. It’s mad funny!

Exit Wounds continued DMX’s hot streak in the theatres. Starring alongside Steven Segal, who plays Orin Boyd, a cop transferred to the worst precinct in the city, X plays Latrell Walker, a boss of a criminal organization who becomes a target of everybody. He connects with Boyd, and the unlikely decide to work together to expose the corruption in the police department. Exit Wounds was another box office X, grossing over $79.9 million worldwide.
 

In Cradle 2 The Grave, DMX plays Anthony Fait, a master thief who pulls off a major jewel heist and evades the SWAT team that's pursuing him. A Taiwanese agent named Su (Jet Li) is attempting to track Fait down so that he can retrieve the stolen black diamonds. But when Fait's daughter (Paige Hurd) is kidnapped by a rival criminal and Su's ex-partner (Mark Dacascos), Su must work with Fait to save the thief's daughter and get his revenge in the process. X and Jet-Li gave us another thrilling action flick.

Never Die Alone stars DMX, with David Arquette and Michael Ealy, and details the story of David (DMX) returning to New York City from the West Coast. When David is fatally stabbed and left for dead, a writer named Paul (Arquette) discovers him and takes him to the hospital. After David is pronounced dead, Paul finds out that the criminal has left him his personal belongings, including audio recordings of his life story. In one of his most dramatic roles, X proved he was a well-rounded actor.  

Dave Chappelle was on fire in 2004 with the hottest comedy show on T.V., Chappelle’s Show. The stand-up superstar would bring the best acts from Hip Hop to perform. He had to get DMX to grace the stage, who was at the top of his game as an MC and a film star. X came through as a guest and performed a scorching medley of “Get It On The Floor,” “DMX (What’s My Name),” and “Ruff Ryders Anthem'' accompanied by Swizz Beatz.

Top Five stars Chris Rock, Rosario Dawson, and Gabrielle Union, and follows comedian and film star Andre Allen (Rock), who’s doing an interview with journalist Chelsea Brown (Dawson) about his career. In one scene, Chris returns to stand up after being in jail and getting a pep talk from DMX. He tells Andre that he does not want to keep rapping and wants to sing instead. He then sings "Smile", as only X can. Although it was a brief cameo, X gave a scene-stealing performance by showing his comedic side.