The potential career avenues that stand before the aging rap star are unquestionably bleak. When faced with the notion of an endlessly improbable comeback album or a gig in reality television, it makes sense for an emcee to volley that golden charisma into a career on the silver screen—and none have traversed the extreme peaks and valleys of both careers quite so noticeably as O’Shea “Ice Cube” Jackson. And though dude’s mounting catalog of mediocre comeback records and shitty films might make him a pretty easy target, there was a brief time when Cube seemed able to wing walk his way into totally legit careers in two mediums. But that was a long time ago.

• Boyz n the Hood/Death Certificate (1991)—Just as his second solo record was striking the platinum bell, Cube made his big screen debut in Boyz n the Hood. John Singleton’s genre-defining gangsta flick introduced the magnificently Jheri-curled Cube as “Doughboy,” a nuanced, appropriately thuggish version of himself.

• Friday (1995)/Recording hiatus (1993-1998)—After more or less single-handedly engineering the archetype of what would become a multi-billion-dollar industry with four consecutive solo albums between 1990-1993, Cube took a long breather to focus on film work, starring in the absurdly successful Friday, which firmly established Cube as a likeable leading man—a development that would successfully curtail his emcee believability indefinitely.

• Are We There Yet? (2005)/Laugh Now, Cry Later (2006)—Though the decade that followed certainly brought more bad (Anaconda, Torque, Ghosts of Mars) than good (Three Kings), Cube never totally washed his hands of tough guy plausibility until he lost that fight with the CG deer in Are We There Yet?. Though followed up with the hard-edged Laugh Now, Cry Later—his third in a line of lackluster comeback albums—Cube’s fate was sealed the minute he signed on for this Mr. Mom bullshit. Next up: The sequel, Are We Done Yet?, out next week.