Dave Chappelle Avoids His Worst Instincts to Anchor a Very Funny SNL

And Your Host…

[Note: Please skip down past the monologue clip if you’d rather not hear my thoughts on why Dave Chappelle’s booking tonight is so divisive. You’ve been warned.]

There’s a trap in being a certain kind of comedian. Building your brand as lone wise man in a world of fools (and it’s almost always a man) inevitably runs up against the reality that you can’t know everything. And if you’ve bought into your own schtick, reflection, adjustment, or—god forbid—apology is out of the question.

So you double down on the stuff you got called out for since, as you’ve been told by fans for your entire career, you are right. Invariably. Inviolably. And, in Dave Chappelle’s case, disqualifyingly. 

Of course, Chappelle’s career hasn’t really become disqualified from anything in the years since his anti-trans bigotry became the most identified theme of his stand-up. He won a Grammy for an album packed with bigoted nonsense against the trans community after he was “cancelled.” He headlines wherever he goes, and invites the most popular of his comic peers to perform literally at his house. 

And now he’s back hosting Saturday Night Live, his fourth such gig a gleeful “f*ck you” to those who’d been relived when he didn’t show up for the post-election hosting slot he’s occupied in recent years. For Lorne Michaels, himself riding the crest of a valedictory “comic genius” wave, booking Dave Chappelle in 2025 not only thumbs the eyes of those “cancel culture” forces the 80-year-old comedy impresario has increasingly railed against in his later years, but acts as his own “How dare you?” to those who’d question his taste and decision making. 

I’ve thought a lot about all this in the lead-up to tonight’s show, and lost not a little sleep over it. Apart from the slew of boorish, grammatically sketchy online idiocy any criticism of Dave Chappelle inspires (don’t worry, I stopped reading your comments a decade ago), that “How dare you?” factor is always lurking. 

Dave Chappelle is a legend, both in stand-up and sketch comedy. And he is, without question, a genius. The way he’s cultivated a guru-like air in his stage persona—the low, measured tone, the defiantly relaxed puffs of punctuating cigarette smoke—only adds to the idea that Dave Chappelle is… correct. I’m as guilty of cutting one of my comic heroes (because he was that) the slack of the disciple. I reviewed one of the first of his specials to edge into transphobia and I glided past it as Chappelle’s comic due. He’s a comic genius and I’m not, so he got a pass.

The thing is, hero worship is an act of willful blindness if you let it be. Drawn to the talent, the charisma, and the myriad gifts they’ve given you in their work, you let things slide, assuming that nothing your hero says or does can be just plain wrong, or ugly, or plain f*cking stupid. Unchecked, this blinkered fandom can lead you into some truly dark places yourself—even as it reveals to the world some dark, ugly, and f*cking stupid places inside yourself. (Here I’ll let the coming Monday’s inauguration speak for itself.) 

Since I’m no self-professed comic genius and all, I’ve had to pull up since and admit to myself that I’d missed the disappointing blind spots in Chappelle’s act. (Notably, my editors at the time never asked me to review one of his specials again.) 

And so here I am, reviewing Dave on Saturday Night Live. Stripping away the starry gaze of fawning fandom for the clearer spectacles of someone who’s learned through hard experience not to elevate anybody past reproach or criticism, I can still admire Chappelle the craftsman, Chappelle the comic force. And I can feel the loss of a hero as I watch the later Dave expertly pushing buttons for their own sake, his confrontational gaze’s implied “How f*cking dare you?” anticipating my any objection.

Last time he hosted, I wasn’t alone in thinking his material about “the Jews” (two words he claimed he wasn’t allowed to put together) was downright creepy. (As a statement from an SNL legend pointed out in advance of tonight’s episode.) And while anti-trans and anti-LGBTQ bigotry is now a central platform of the controlling political party in America, I’m going to go ahead and say that I think Chappelle’s continued attacks of trans people are f*cking bullsh*t. 

I don’t imagine Chappelle thought his passing trans material would become so identified with him and his comedy. But that’s the trap—called out on his bigotry, he had no choice but to double down. So now he finds himself championed by bigoted yahoos of the type he famously mocked and abandoned for laughing wrong at Chappelle’s Show. Dave Chappelle is now championed as much by braying loudmouths for whom punching down is sport, as he is by fans of great stand-up. Like that defiant cigarette, Dave Chappelle is addicted to a toxic habit.

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And that’s a damn shame, because Chappelle’s monologue tonight was outstanding. Looking razor-sharp in a suit rather than the boiler suit he’s favored in recent years, Chappelle was even sharper. Easing himself onto a provided stool and unhurriedly smoking his cigarette down to the filter throughout, Chappelle ran through his roster of topics (the L.A. wildfires, Diddy, and Trump, inevitably) with the storytelling confidence that’s his signature. 

Throughout, Chappelle played his audience like a virtuoso. Addressing his absence from the post-election episode, the host asserted dominance over his host, claiming that he’d been asked, but put Lorne off until he finally caved in as a favor. (Picturing Chappelle telling Michaels “Naw man, I’m cool” is pretty baller.)

Chappelle winked at the crowd, first in tone and then literally after claiming, “I’m tired of being controversial.” To be clear, “controversial” is not the issue—far from it. The best comedians confront audiences with their own blind spots and unquestioned assumptions, big and small, and make them laugh even as they bridle at the confrontation. (The trick is not being adamantly wrong while attacking the wrong targets, but we’ve covered that.)

Calling jokes about the still-happening fires “way too soon,” Chappelle yet plowed ahead. Decrying those leaving unsympathetic comments on stories of rich Californians (like Chappelle’s Men in Tights co-star Cary Elwes) losing their homes led to Chappelle swerving to state, “That’s why I hate poor people.” A joke that started out by mocking the conspiracy peddlers rushing to whip up hate and disinformation saw Chappelle deadpan his way into an explosive laugh as he intoned, “As a rational thinking person, you have to consider the possibility that God hates these people.” His follow-up exclamation, “Sodomites!” and a succeeding joke about West Hollywood (“You can’t burn what’s already flaming”) walked several lines simultaneously without betraying the internal irony. (At least according to this old straight guy who’s willing to hear otherwise from LGBTQ people. You know, since I’m not a comic genius and all.)

Same goes for his segue into the Trump material Chappelle claimed he was preparing to “get rid of” before inauguration. Chappelle is masterful at drawing audiences in by getting serious and soulful about something he actually cares about, then yanking the rug out without invalidating the premise. Chappelle brought real, personal outrage to Donald Trump and the GOP’s lies about Ohio’s Haitian immigrant community, noting how he lives literally next door to Springfield and how he made a point of supporting that community’s beleaguered-by-bigots restaurants after Trump whipped up a racist frenzy about kidnapped and devoured pets. That Chappelle then made a joke about not know what exactly he ate at those restaurants (“but it fell right off the bone”) is a rhetorical twist that winks at the manufactured controversy but doesn’t overshadow his earlier rundown of just how industrious and necessary that maligned community was to their new home and how ludicrous were Trump’s lies. Again, this is the Dave Chappelle that makes you remember.

His Diddy material was less pointed, but funnier, a wide-ranging peep into a scandal everyone assumes he had more knowledge of than he claims. The punchline about finding out he’s too ugly to have been invited to the under-investigation music mogul’s “freak-offs” comes at the end of one of those somber, searching set-ups, and it’s all the better for it. I have no idea about the rumor Chappelle relates about Diddy and a certain beloved sitcom dad (even he admits it’s from the internet sewer), but he uses the alleged anecdote to hang a series of solid jokes. (And throws in an undisguised jerk-off pantomime the FCC might have thoughts about.)

It’s here also that Chappelle, discussing the 55-year-old Diddy’s age (“This n***er’s paying half price at the movies!”) where the 51-year-old Chappelle delivers the telling advice, “You’re supposed to evolve and grow past your mistakes.” Indeed.

Closing out the marathon monologue, Chappelle was, once again, in guru mode of the sort one imagines Lorne Michaels and SNL were trying to book for the post-election show. (Stand-in and Chappelle Show pal Bill Burr shanked that one pretty hard, as it turns out.) Noting how “most of” the nation’s flags will be at half-staff for the inauguration (unless your governor is a Republican looking to do some preemptive boot-licking) to honor Jimmy Carter’s passing, Chappelle told a story. About Carter’s visit to Palestine, which the former President called by name in the title of his book, Palestine, Peace Not Apartheid, angering many of his Israeli hosts. Choosing to visit the beleaguered occupied region despite the Israeli government withholding protection out of spite was, according to Chappelle, unironically decent and heroic.

Finally addressing Donald Trump himself, as is a legend’s prerogative (“I know you watch the show”), Chappelle made the sort of damning comparison that, in a better America, would carry enormous weight. “I don’t know if thats a good President,” Chappelle said of Carter, “but that right there I’m sure is a great man.” Noting that the presidency is “no place for petty people,” Chappelle, again speaking directly to an incoming president whose baby-sensitive ego is guaranteed to be watching, concluded, “Good luck. Please do better next time.”

It’s moments like this that make me mourn what I’ve lost in Dave Chappelle, even as I acknowledge, with the dreadful wisdom of age and perpetual disillusionment, that seeing people for who they really are is the smarter play. There’s nobody with the comic authority who could stand on that stage, stare straight down the barrel, and urge Donald Trump to not “forget your humanity” with as much power. Now, Donald Trump is constitutionally bereft of humanity and will react with nothing but scorn and grade school-level insults, but even his most feverish cultists can’t ignore where this criticism is coming from. That’s the power of Dave Chappelle. And that’s why it’s so damned disillusioning that he can’t take his own advice.

The Best and the Rest

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The Best: While running a distant second in the Chappelle comic legacy, Dave’s skills as a sketch performer are nothing to sneeze at. Deprived of his old pre-taped safety net means nothing, as, in the evacuation sketch, Chappelle proved himself a force of comic nature. The one sketch to address the wildfires, the premise sees the evacuation alert send family man Chappelle into a frenzy of manic panic, as he smashes a wall with a sledgehammer to retrieve a Walter White-sized cache of cash, reveals a secret compartment full of guns and a thumb drive he orders bewildered wife Ego Nwodim to hide up herself, opens the secret bookcase where his even more secret French family lives, and berates son Devon Walker for having been raised too soft to deal with Michael Longfellow’s Serbian assassin. Chappelle also graphically guts the adorable family pooch (puppet) to yank out the cellphone into which he barks orders in Mandarin, the sketch’s second deployment of the trusty spurting blood rig.

The whole sketch whirls along on Chappelle’s unerring dynamism, never pausing to over-explain or belabor the premise. It’s just Dave committing to a sketch as a character, something his hosting stints usually don’t have much time for. (Again, those monologues chomp up a show-unbalancing amount of screen time.) When the alert turns out to be a false alarm, all Chappelle’s outed shady dad can do is look around his blood-spattered home, sarcastically clap his bloody hands in the face of his disgusted family, and tell them to pull the pager out of the cat’s ass if the unfortunate creature ever turns up. Not a sketch about the wildfires per se, the piece piggybacks on a topical tragedy to establish its human, and deeply funny, stakes. Outstanding stuff.

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The Worst: As usual, there wasn’t a whole lot of space left for sketches on a Chappelle-hosted show. Dave did fine work in a few pieces right at the top and then was completely absent from live sketches after Update. Not that there were many, so it falls to the police sketch for this slot.

I question the whole idea behind this one—Devon Walker’s boyfriend is so afraid of offending his missing girlfriend by giving her actual weight, age, or occupation that he listens to Kenan’s janitor (or Kenan’s pantomimed advice anyway), leaving the sketch artist to whip up the idealized image of a boardwalk caricaturist. One: Who doesn’t have a photograph? Two: The whole thing smacks of relationship stereotypes to the extent that Walker comes off like an uncaring jerk. (Mikey Day and Bowen Yang’s attending cops play straight man with a similar lack of urgency as to the safety of a missing woman.)

It was a good night for Walker who—as my time on a recent podcast taught me—is shockingly the cast member with the least screen time in the first half of Season 50. But it’s not especially impactful screen time, as—no shocker here—Kenan gets the sketch’s only laughs. Thompson can play a sly, beaming background character like this without breaking stride, and his janitor delivers his questionable advice with silently amusing physicality. (His “mind blown” gesture after Walker triumphantly one-ups his pandering description of the, again, missing woman is yet pretty funny.)

The Rest: As noted, no room for any other sketches not slotted into their own sections below.

Weekend Update Update

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It was no Dave Chappelle monologue or anything, but tonight’s Update clocked in at a whopping 15-plus minutes, comprising Jost and Che and two extended desk pieces. All of them hit in different ways, making for a more varied and weighty middle stretch of a top-heavy show.

Going into America’s second round of self-inflicted chaos and ugliness, perhaps Jost and Che have the right idea. As the cold open suggested, nobody in the media (except maybe John Oliver—please come back soon) has any strategy how to deal with this preening creep’s daily toxic spill of alternating brain-sludge gibberish and hateful policy, so simply flooding the zone right back with mockery and ridicule is at least fighting absurdity with absurdity. The jokes tonight were signature Jost and Che—pointed and glib, delivered with an above-it-all smirk.

But the jokes were good, even beyond the public service aspect of reminding viewers of each horrifying cabinet pick, subserviently greedy oligarch, and occasional terrifying presidential portrait. Jost mocked Trump’s laughably try-hard tough guy lighting as being illuminated from below by “the fires of hell.” Che, joining most late-night comics in these waning days of the Biden administration, slipped in one of those super-hilarious “Biden sure is old” film clips, but Jost at least nodded to the relatively sane and stable world we’re leaving by noting how Biden’s farewell address carried an unspoken refrain of “you ungrateful bastards.”

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Che mocked alpha male Trump moving his inauguration inside the Capitol ’cause it’s gonna be chilly (“Hey, just like last time!,” he joked over a photo of the January 6 insurrectionists scaling the walls), while Jost made a joke about Mark Zuckerberg blowing Trump in subservient fealty. Jost mocked the upcoming farce that is Robert F. Kennedy Jr’s confirmation hearing by mocking his ever-darkening tan being set to Tropic Thunder setting, and used the brewing feud between MAGA meatballs Steve Bannon and Elon Musk to make Bannon as Jabba joke.

Jost and Che have honed their double act to such an effortless edge that plucking out the hard hitting gags from the rest is a matter of speed-enjoying. (Che joked about an aircraft carrier named after Bill Clinton being “covered in seamen,” to give example of the latter.) But, again, the record-shattering tenure of Jost and Che hasn’t been about making Update into a coherent fake news satire, but to show off the talents of two very funny, very different comics at their smart-alecky best.

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Michael Longfellow made a long-awaited return as himself, performing a chunk of stand-up about TikTok, which went dark as the show was airing. Leaning into his persona as devilish millennial, Longfellow called his outrage at the congress and SCOTUS-approved ban as “the first political opinion I’ve ever had,” and cited such TikTok-endorsed facts as Jesus Christ being Chinese and prescribing him adderall for proof of the app’s usefulness.

Che played able straight man as he pointed out the very real privacy concerns surrounding the Chinese-owned app, with Longfellow responding in his eternally amusing detached manner that he’s not really worried that a website knows he’s into “thicc Latinas,” even as he frets about what he’s going to watch at the movies now. He also tries to swipe Che’s understandable objections away in the air, to no avail.

Longfellow’s whole vibe is a natural fit for SNL—he makes a great mischievous game show host and (looking at rumors of Che and Jost’s departure) would bring some early Chevy Chase energy to the Update desk. Like Walker, I was surprised at just how little the show has used him this season so far, so here’s hoping this appearance means a broader scope for the guy going forward.

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And then there’s Sarah Sherman in full Nosferatu makeup. Another big night for Sherman saw her kitted out like old school Max Schreck to complain about not getting even an audition for Robert Eggers’ updated vampire flick. Of course, any Sherman Update appearance is going to veer into Jost abuse at some point, so most of the laughs came from her reaching out her impressively spindly spider-fingers to the flinching Jost’s face, claiming that she’s been horrified by the anchor’s exposed penis, and calling out Jost’s supposed snootful of cocaine. I also like when SNL does a little stylistic tinkering to formula, as with Sherman’s shadow-first approach to the desk and the black-and-white scare pose insert shots. (You’ll see them on YouTube, studio audience.)

Political Comedy Report

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I din’t hate the cold open, an MSNBC panel show headed by Sarah Sherman’s Rachel Maddow and finding one strong comic idea and sticking with it. The idea that the media has woefully failed America by chasing every idiot social media nonsense thumbed by Trump on his gold crapper rather than grappling with the very real and substantive threats he poses is—let’s call it—relevant. And so having Maddow and her panel promise to talk about the rise of unelected oligarchs stealing our democracy and Trump’s larcenous looting of the government while his hand-picked minions trample all concept of civil rights and the Constitution only to be interrupted by a series of network-branded news breaks like “Trump proposes trading Connecticut for Italy” and “Trump challenges Chinese President Xi Jinping to a UFC fight” is consistently funny and pointedly escalating.

I’m not enough of an MSNBC-head to know if the sketch’s digs at talking heads like Marcello Hernandez’s Ari Melber trying too hard to establish his youth cred with rap lyrics or Chloe Fineman’s Stephanie Ruhle being a preening sex kitten are anything, but it at least gave the characterizations a little juice. When Sherman’s Maddow, trying to steer things back to actual news only to bail out of her talk of Trump’s aluminum tariffs for being too boring even for her, it reinforces the point nicely that corporate news as presently evolved is constitutionally incapable of behaving like anything but a kitten with some dangly string when it comes to covering Donald Trump.

As for Trump himself, James Austin Johnson made his appearance as the hosts gave up and simply threw to Trump’s latest live gibberish, this time babbling on about the now in effect TikTok ban and introducing Bowen Yang’s George Santos as the newly created Secretary of Fact-Checking and Ambassador to Sephora. Twofold above-average for these sorts of cold opens, JAJ’s always eerily amusing Trump underscored the incoming president’s transactional loyalty and wind sock principles (TikTok’s fact-free targeted youth disinformation helped him win, so he loves it now), and the lunatic danger posed by Trump’s raft of unqualified nominee hatchet-men. Again, the bar is pretty low for these sorts of sketches, so simply maintaining a consistent point of view on a relevant topic is a promising sign going into the next four years of this.

Recurring Sketch Report

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It’s a good boost when a visiting comedy icon undisguisedly laughs during your sketch. So congrats to Marcello Hernandez, who visibly appeared to crack Chappelle up during the Immigrant Dad Talk Show. (Hernandez was the butt of the joke in one of this week’s promos, where GloRilla informed him that an effusive Dave only tells people they’re one of his favorite comics to be polite, but this seemed like the real deal.)

Immigrant Dad Talk Show is indeed a fine spotlight for breakout star Hernandez, even if the premise is a little one note. (First-gen immigrant dads disapprove of their assimilating kids’ softness, don’t you know.) Chappelle, on hand as Hernandez’s equally dismissive Black neighbor calls guest white dad Mikey day a p*ssy for being supportive and affectionate with his teen son, a stance the sketch essentially endorses by playing Day and son Andrew Dismukes’ “Tom Brady”-style mouth kiss for audience squeals and derision.

Still, Hernandez’s characterization is energetic and funny, even if he relies a bit too much on puns in his insults. (“Vegan talk about this after you eat this chicken,” he berates his son.) SNL loves a broad caricature, and broad immigrant comedy goes all the way back to its Wild and Crazy days, so tradition upheld, I guess. (I still recall how Tim Robbins’ increasingly prescient satire Bob Roberts had his fascist politician guest-hosting supposed edgy and subversive late-night show Cutting Edge Live, where he was eager to follow a sketch simple titled “The Immigrant Family.”)

That said, there are some subtler points buried amidst the garrulous stereotyping. The forced proximity of the three clashing dads brings up gentrification without ever saying the word. And, again, props to Marcello for impressing the right guest host.

Not Ready for Prime Time Power Rankings

As noted, a few cast members finally got some much needed airtime tonight. Longfellow reminded people what he can bring, and Devon reminded viewers he exists—and that he needs to get opportinities beyond “exasperated straight man.”

No such luck for Jane Wickline and Ashley Padilla, who were only in the dating show pre-tape. In mostly non-speaking roles at that. Still, no lines are better than no anything, as poor Emil Wakim discovered.

Kenan was in one sketch. He killed, because he’s Kenan, but the rumors that he’s easing himself out the door are feeling truer by the episode.

Marcello had a big, first-past–the-monologue hit, but this was Sarah Sherman’s show, as so many have been this season. If any of you out there thought the erstwhile Sarah Squirm was going to be one of this cast’s go-to stars, you’re better at predicting stuff than I am.

Ten-To-Oneland Report

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Speaking of Chappelle’s sketch legacy, the tradition of Chappelle’s Show characters crossing over into a Sketch TV Universe (the STVU) continued as a filmed dating show sketch featured a quick-hit return of Chappelle’s pimp (sorry, “purveyor of precious goods and services”) Silky Johnson. The impeccably smooth Johnson popped in only to see all the female contestants immediately pop their balloons (the show’s voting system) as his misogynistic schtick played out.

Mocking reality TV is what it is at this point, but there were a few funny touches along with Chappelle (and sidekick Donnell Rawlings)’s welcome cameo. (The offscreen sound of a fusillade of popped balloons greeting Kenan’s unimpressive would-be suitor was great.) Overall, the filmed piece felt like something kept at the ready in case Chappelle’s monologue went typically over (tonight’s clocked in at a whopping, unhurried, and what I believe the brave souls at SNL By the Numbers will confirm as a record 17 minutes.) But it worked well enough even without the Chappelle’s Show nostalgia factor.

Stray Observations

Speaking of my site-mates at SNL By the Numbers, I was the guest on that podcast’s mid-season rundown episode last week. Tune in to find out what I look and sound like (eh), and stay for the eye-opening stat-work and a surprise appearance from my very impatient cat. Cooper.

Speaking of Cooper (full name Special Agent Dale Cooper), tonight’s RIP title card paid tribute to David Lynch, who died on Thursday. While I can’t recall any specific David Lynch/SNL connection off hand (apart from an offscreen impersonation cameo in Kyle McLachlan’s hilarious Twin Peaks-era monologue), it’s only right and proper for anyone with a platform to honor the passing of one of the truest, most original, and damnedest movie artists we’ve ever seen. we shall not see his like again.

Inspired by Chappelle’s monologue plea, I made a mid-review donation to www.socalfirefund.org, which was plugged during the show tonight. Join me it’s within your means.

Perhaps trying to insert some of that joke swap magic to the Nosferatu desk piece, Jost read out his thoughts on period sex (“If there’s blood on the field, play ball”) with the abashed cadence of someone reading a cue card joke for the first time on air.

NYC is putting f*cking spikes on subway gates to deter/maim $3 turnstile-jumpers? Eric Adams’ visit to Mar-a-Lago is making more and more sense.

GloRilla killed it, two times.

I don’t envy James Austin Johnson. Donald Trump has made it abundantly clear he’s going to use thin-skinned dictatorial abuses to punish critics and media outlets that dare make fun of him, so Johnson is right in the firing line. Of course, this being Saturday Night Live and Lorne being 2025-vintage Lorne, Johnson may be cushioned by preemptive self-censorship from a show whose rebellious, truth-to-power myth has always outpaced its actual comedy courage.

Episode Grade: A solid B.

Next week: Our host will be Timothée Chalamet alongside musical guest… Timothée Chalamet? Tune in to see how that all turns out.

6 Comments

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  1. drn211 says:

    There is no direct connection to Lynch. Bob Uecker who actually hosted the show should have been given the honor of that before goodnights card instead.

  2. Lina says:

    Hated nearly everything about this episode and its never-ending asshole parade. Literally, just men being assholes for the whole show. Sarah Sherman on update was by far the standout and the cold open was pretty on point. Ch*ppelle is just so high on his own supply. A revolting, arrogant, asshole, millionaire contrarian hypocrite of a man. And his monologue sucked.

    1. Lina says:

      And ya know what else? He has the most embarrassing fashion sense I’ve ever seen on a man, and it gets more stupid the older he gets.

    2. Patrick S. Tomlinson says:

      You sound like a real treat, Lina.

  3. Kasota Stone says:

    was he doing a Dick Gregory homage?

  4. Leo says:

    How much money do they save by having Chappelle on and doing a 17 minute monologue?

    It’s got to be much cheaper than someone doing a 5 minute monologue with production values.

    Also, the long monologue cuts a couple sketches out of the show so that saves a huge amount of money.

    So with Chappelle ‘s 17 minute monologue, what do they save? $200k? More?