Stream It Or Skip It: ‘Chappelle’s Home Team Presents Donnell Rawlings: A New Day’ On Netflix, Where The Third Taping’s The Charm?

Dave Chappelle’s Home Team is a four-special series announced by Netflix in 2022, with installments so far released by Earthquake that year, and Luenell last year. Which makes Donnell Rawlings the third in Chappelle’s Home Team series, and it took Rawlings three tries to film his installment, finally getting it wrapped last November during the New York Comedy Festival. So is the third time the charm for Rawlings? Even if it’s not, he already seems quite content with where he’s at right now in both his personal and professional life. That much comes through most definitely.

CHAPPELLE’S HOME TEAM PRESENTS DONNELL RAWLINGS: A NEW DAY: STREAM IT OR SKIP IT?

The Gist: Rawlings, like Chappelle, grew up in and around Washington, D.C., but whereas Chappelle went straight into stand-up as a teen, Rawlings enlisted in the U.S. Air Force, serving both at home and abroad in South Korea.

When Rawlings did enter show business, he did so with flourish, not only as “Ashy Larry” and other characters on Chappelle’s Show, but also “Day-Day” on The Wire, and much more recently Alvin on BMF, Mr. Earl in Winning Time: The Rise of The Lakers Dynasty, and the voice of Dez in the Pixar/Disney+ film, Soul.

Although you’ve seen him showcased on Netflix in Snoop Dogg’s F*cn Around Comedy Special, or on tour with Chappelle, this is indeed Rawling’s first solo stand-up special, which clocks in just under a brisk 40 minutes, with the comedian riffing on getting older, feeling exotic while visiting New Zealand, and surviving both toxic relationships, dating, and co-parenting his young son.

Memorable Jokes: Rawlings gets off to a memorable start, with a vignette set to Nina Simone’s “Feeling Good” that opens in the country woods with birds chirping at sunrise, the comedian smiling while observing his son, then seemlessly cutting his stride into the Hard Rock Hotel’s venue near Manhattan’s Times Square, where Rawlings joins the music just in time to grab the mic and belt out: “And I’m feeling good!” Why? “Because I ain’t ashy no more!”

After a brief observational bit about that Alabama dock fight that went viral last summer, Rawlings turns the attention toward himself.

He acknowledges that a toxic relationship with a woman who claimed Rawlings was a narcissist prompted him to realize he sometimes feels like Taylor Swift in her hit song, “Anti-Hero.” On the flip side of life and the world, Rawlings explained how the lack of other black people in New Zealand made him feel exotic to the point where he thought he could trick white women into thinking he was Idris Elba. That worked until one woman recognized him: “That’s Ashy Larry, dummy!” 

Rawlings enjoyed much greater success dating white women in the States; that is, until he watched and listened to too much of Dr. Umar Johnson, whom the comedian called the blackest man on the internet.

Even so, Rawlings feels free enough to talk openly about his history of dating not only white women but also women young enough to be his daughter. “I’m older than my baby mother’s mother,” he acknowledges. He demonstrates through act-outs why he cannot bring himself to date women closer to his age, while simultaneously claiming a different rationale for why he dates so young. He’s too famous, he says. Or in words he has been saying for over 20 years now: “I’m rich bitch!”

Our Take: Rawlings is right to be feeling good, even if he’s co-parenting and seemingly unwilling to date women his own age, let alone sustain a relationship with these younger women, even when that woman is the mother of his son. But we don’t judge comedy by someone’s offstage personal conduct, do we?

I suppose if they address that conduct onstage, then we can assess how sincerely and how humorously they go about it. At times Rawlings is forthright about owning his faults; at others, he wants to make the case that he’s right to pursue toxic or inappropriate relationships.

The relationship that’s most curious, of course, is Rawlings’ longtime friendship and association with the comedian who got him on Netflix and executive-produced his debut special. Rawlings is five years Chappelle’s senior, but has always seemed less big brother and more wacky sidekick to the insanely famous Chappelle. That relationship is not only enhanced by Rawlings opening for Chappelle on tour some two decades after their Comedy Central series, but also by Rawlings deciding to relocate to Chappelle’s hometown of Yellow Springs, Ohio.

In that context, Rawling’s two bits that directly or indirectly mention the LGBTQ+ community are worth noting for how relatively tame and generous they are. Early in the set, Rawlings claims that gay black men make the best potato salad, and says he can back that up through first-hand experience tasting his older brother’s dish. Later, when Rawlings talks about the highlights and lowlights of co-parenting his 8-year-old son, he quips: “Being an older dad, I think I’m a dad that identifies as a mom.” Pause. “So does that make me trans-parent?”

It’s silly and punny, but it nods to our changing times without being needlessly cruel and unnecessary. If only Chappelle could be so transparent.

Our Call: It might not win any awards or hit your Top 10 list for putting the special in comedy special, but sometimes a straight-forward 40 minutes of comedy helps free you from the rigors of the real world and zone out for a few laughs. If that’s what you need, then by all means STREAM IT and perhaps you’ll also gain more insight into Chappelle’s world, too.

Sean L. McCarthy works the comedy beat. He also podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.