Born Craig Philip Robinson on Oct. 25, 1971, in Chicago, IL, he developed a flair for comedy early in life, entertaining his family with his imitations of Richard Nixon. His father recognized his talents and encouraged a curious reversal of roles wherein Craig would read him and other family members stories such as “The Three Little Pigs” and insert his own offbeat real-world embellishments. He also studied music as a youth, becoming particularly proficient on keyboard instruments. After high school, he attended Illinois State University in Normal, IL, where friends urged him to try stand-up comedy. In 1994, he returned to Chicago to earn a master’s degree in education at Saint Xavier University, going on to teach music at the city’s Horace Mann Elementary and to take improv classes at The Second City. Initially bombing, he added the twist of sitting on stage behind his Roland keyboard and telling tales of personal heartache while accompanying himself. In 1999, he moved to Los Angeles, where he hooked up with fellow Second City – and comedy bellwether “Mr. Show” (HBO, 1995-98) – alum Jerry Minor, to create the stage act, L. Witherspoon & Chucky.
A faux R&B act with Minor as L. Witherspoon, a smooth-as-silk singer à la R. Kelly, and Robinson as Chucky, his keyboardist and backup singer, they played live and made it on to national TV on HBO’s “Real Time with Bill Maher” (2003- ), often performing their “hit” song “Somebody’s F*cking My Lady” (it turns out it is Chucky). Robinson began picking up TV work, initially guest shots on such comedies as “Lucky” (FX, 2003), “The Bernie Mac Show” (FOX, 2001-06) and “Arrested Development” (FOX, 2003-06). In 2005, the producers of the American version of “The Office” (NBC, 2005- ), cast him as Darryl Philbin, the stoic, blue-collar warehouse manager occasionally made to suffer through and abide the machinations of the show’s loopy white-collar denizens. Though initially just comprising the occasional appearance, Darryl was written more and more into the show and eventually made a regular castmember. Robinson found himself more in demand, picking up a curious job in the Korean CGI-heavy monster film “D-War” (2007); as big a hit in Korea as it was a flop in the U.S., and brief parts in Tyler Perry’s “Daddy’s Little Girls” (2007) and “Walk Hard: The Dewey Cox Story” (2007).
Also in 2007, director Judd Apatow – just off the success of his ribald, largely improvised comedy “The 40 Year Old Virgin” (2005) starring Steve Carell and Seth Rogen – cast Robinson in his next untoward outing, “Knocked Up,” the tale of a mismatched couple (Seth Rogen and Katherine Heigl) whose drunken coupling inadvertently results in a pregnancy. Robinson, in only a few minutes of screen time, shone as the doorman at a hipster club. The next year would see him twice reteamed with Rogen; initially as the complex drug capo in the messy stoner/action film hybrid, “Pineapple Express” (2008). And when director Kevin Smith tapped Rogen for his own bawdy outing, “Zack and Miri Make a Porno” (2008), Rogen pushed for Robinson for the role of his best friend. For the Apatovian comedy about two down-on-their-luck friends (Rogen and Elizabeth Banks) who decide to make an adult film, Robinson played a wife-beset coffee-shop worker recruited by Rogen’s character to be the film’s “producer,” to great comic effect; particularly in a memorably, mostly improvised scene between him and Tisha Campbell-Martin. The New York Times made particular note that Robinson “is fast becoming the most dependable comic counterpuncher in the business and who needs some bigger roles or a sitcom of his own right away.”
But some lows accompanied his career highs. In August 2008, police officers pulled Robinson over in L.A. on a traffic violation and determined him to be intoxicated; a subsequent search of his car turned up illegal drugs. Subsequent investigation found him to be under the influence of cocaine, amphetamines and marijuana. The next week Robinson pled guilty to possession of a controlled substance, but he agreed to attend drug education classes, with the charges to be dismissed upon his completion of the program. The bust did little to disrupt his upward trajectory. Robinson had a flurry of cameos in the likes of “Fanboys” (2008), “Prop 8: The Musical” (2008), “Miss March” (2009), “Post Grad” (2009), “The Goods: Live Hard, Sell Hard” (2009), “Night at the Museum: Battle of the Smithsonian” (2009), and “Shrek Forever After” (2010), as well as turning up in select comic one-offs such as the Gunn brothers’ web series “PG Porn” and Comedy Central’s “Reno 911” (2003-09). He snared his biggest billing to date in the John Cusack-produced feature “Hot Tub Time Machine” (2010), with Robinson starring alongside Cusack and Rob Corddry as guys in the throes of mid-life crises who pass out in a resort hot tub and wake up to find themselves transported back to the 1980s with a chance to change their lives for the better. Robinson received excellent reviews for his work in the goofy comedy.
While continuing his work on both “The Office” and “Eastbound and Down,” Robinson added another recurring role to his arsenal, appearing regularly on “The Cleveland Show” (Fox 2009-2013) as LeVar “Freight Train” Brown, the domineering father of Cleveland Brown (Mike Henry). Robinson’s first leading role in a film came in Tina Gordon Chism’s “Peeples” (2013), a romantic comedy in which he played Wade Walker, a well-meaning but hapless man attempting to ingratiate himself to the upper-middle-class family of his new fiancée (Kerry Washington). He also rejoined his “Pineapple Express” cohorts for “This Is The End” (2013), a film written and directed by Seth Rogen and Evan Goldberg in which Robinson, Rogen, Jonah Hill, James Franco and Danny McBride play fictionalized versions of themselves stranded in the Hollywood Hills in the aftermath of the apocalypse.