In 2000, Cannon made the jump to film with a brief appearance in the romantic comedy, “Whatever It Takes,” followed by another small role in the hit sequel, “Men In Black II” (2002). That same year, Cannon had a breakout role as the star of "The Nick Cannon Show” (Nickelodeon, 2001-2003), on which he also served as creator and executive producer. But it was the feature "Drumline” (2003) that propelled him into stardom. In this coming-of-age tale centered in the world of showstyle marching bands, Cannon played Devon, a drummer from Harlem with a chip on his shoulder who earns a scholarship to a fictional Atlanta university. Though his brash attitude rubs the band director (Orlando Jones) and drumline captain (Leonard Roberts) the wrong way, Devon is given the chance to display his incredible talent, but he must learn to be part of the team. “Drumline” was a surprise hit, making over $56 million at the box office against its modest budget, while earning steady kudos from critics.

Off the success of “Drumline,” Cannon began landing more roles in feature films. In “Love Don’t Cost a Thing” (2003), a remake of “Can’t Buy Me Love” (1987), he played an egghead teenager dedicated to his studies and building an engine that will get him into college. But when the school’s popular girl (Christina Milian) wrecks her mom’s Escalade, the übergeek hatches a plan that forces her to be his girlfriend for two weeks while he repairs the damaged vehicle. Despite the charm of the two leads, the flimsy romantic comedy fell flat with audiences and critics alike. After voicing Louis in “Garfield” (2004), he waxed poetic as the Thoreau-quoting assistant to a private investigator (Richard Jenkins) in the dance-themed romantic comedy, “Shall We Dance?” (2004). Cannon then concocted the idea for “The Underclassman” (2005), a by-the-book yawner about a maverick cop (Cannon) whose youthful looks allow him to go undercover at an elite private high school after a student turns up murdered. Clichéd action, lame one-liners and box office misery ensued.