Don Cheadle’s not letting all that War Machine money go to his head, or his work ethic, as exhibited in his Monday sit-down with Conan O’Brien. Apart from popping by Conan’s pandemic temporary HQ of Largo at the Coronet for an in-person (if socially distanced) chat, the acclaimed actor is starring in the third season of Showtime’s Black Monday, squaring off against LeBron James in the upcoming Space Jam sequel, costarring alongside Benicio Del Toro and Jon Hamm in Steven Soderbergh’s Detroit-set noir No Sudden Moves, and displacing Daniel Stern as the narrator of The Wonder Years reboot. Oh, and he has a little MCU TV franchise coming out at some point, to keep that War Machine machine humming along.
So, pretty busy guy. Still, as Cheadle told super-fan O’Brien, there was a time when the nine-time Emmy/one-time Oscar nominee contemplated completely dominating several different entertainment fields instead. Still a huge jazz aficionado today, Cheadle told Conan that his initial plans to be the next Cannonball Adderley or Charlie Parker were only derailed by the fact that jazz required some serious math-like study of form and structure. “I would just go into a fog,” admitted Cheadle, who then sat still for O’Brien’s boastful attempt at jazz scatting. (Pretty impressive high note, it has to be grudgingly admitted.)
Then there was stand-up, a form which the 17-year-old Cheadle thought confidently he had mastered after he and a high school pal snuck onto and open mic stage for two well-received comedy sets. (Cheadle tip for young aspiring comics: Jokes about pooping popes and the “objectively unfunny” antics of comics page stalwarts Nancy and Sluggo always kill.) Sadly—or fortunately, considering Cheadle’s eventual acting success and the joy he’s brought to our lives—the third time (with eager family and friends in attendance) showed the duo that comedy is, indeed, harder than drama, as their epic bombing put an end to that dream.
Rocking a snappy bowler in a way only a Don Cheadle can, the actor then reminisced about how even his chosen art form has seen him sometimes muddling his way through. Recalling the memorably heartbreaking and hilarious Boogie Nights scene where his failed stereo salesman and perpetually downtrodden porn industry character actor Buck Swope trots out a new “Earth, Wind & Fire”-meets-Rick James party ensemble, Cheadle explained the “Japanese koan” that was Paul Thomas Anderson’s direction. (Cheadle tip: If you need to play your character’s existential ennui and hopelessness, spend your take puzzling the difference between “feeling nothing” and “doing nothing.”)