Two years ago, reviewing a rare Dave Chappelle UK gig, I felt like a party pooper for pointing out the sometimes crass and chauvinistic tendencies behind Chappelle’s legend status and rock star veneer. Well, the party’s been well and truly pooped now, after the first two of Chappelle’s three new Netflix specials – for each of which he’s reportedly collecting $20m – met with anger at their apparent homophobia and transphobia. So: is Chappelle practising that classic comedy chestnut, “ironic bigotry”? Or can it be that a comic revered for his contribution to racial discourse in the US, primarily via his sketch series Chappelle’s Show, may be insensitive to discrimination based on sexuality and gender?

I could quote amply from the two sets – recorded in 2015 and 2016 – to cite Chappelle’s gay- and trans-bashing. Plenty other commentators have, to a degree that feels queasy – because it’s easy, and often unfair, to make comedians appear “offensive” out of context. But there’s no denying that Chappelle spends substantial time across the two shows joking about gay and transgender people, usually from the perspective of a bemused straight man who finds those other identities inherently amusing. In one routine, he dismisses a gay man’s campaign to remove the words “husband” and “wife” from marriage licenses by advising: “Whichever one of you is gayer, that’s the wife.” In another, he’s dismayed at having to “mess up my pronoun game” to accommodate a trans woman he mistakenly refers to as “he”.

“Just being real,” Chappelle keeps saying, by way of an apology. He’s not, then, being ironic, in the sense that (for example) Ricky Gervais’s jokes are ironic. Chappelle doesn’t couch these routines in winking inverted commas; nor does he wear a Gervais-a-like smirk to signal devil’s advocate intent. He does hedge the jokes with caveats, mind you, repeatedly claiming that he respects and defends everyone’s right to live as they please.

But that rings tenuous across the span of the two sets, which see the world exclusively through a straight, black male lens, making minimal effort to imagine what life is like for anyone else. (I should add that Chappelle’s material on women – lots of rape jokes and routines about the word “pussy” – are as retrograde as his LGBT material.)

Rich, powerful straight male with huge audience mocking the beleaguered isn’t a good look

I saw Gervais recently – touring his new show Humanity – and he too is cracking jokes about trans people. It’s a little deflating: two progressive icons of contemporary comedy (although Gervais couldn’t touch Chappelle for political potency) having such a tin ear for the touchstone issues of the generation below theirs. In part, this is about the successful comedian’s trajectory from underdog to top dog. When you’re at the bottom of the heap, you tend to punch upwards – and even if you punch sideways, your own powerlessness cuts you some slack. When you’re a lauded multimillionaire, the context of your jokes has changed. Rich, powerful straight male with huge audience mocking the beleaguered isn’t a good look.

It can work, though, if the joke has nuance, or if – however crass it all appears on paper – there’s some mollifying factor at play in the telling. I enjoyed Gervais’s show as a whole, and found that – when he did address sensitive subjects – he erred on just the right side of cruel. (That argument feels harder to sustain after his smug remarks last week on social media, when two grieving parents protested at his cot death material.) I could indulge one or two of Chappelle’s gay or trans gags, too – given that there’s excellent material elsewhere (the Martin Luther King/sneaker deal riff, say), that some (not all) of his provocative material is thoughtful and worth saying, and that in terms of technique, he’s such a masterly standup.

I also think it’s the comedian’s job, to an extent, to probe fault lines, social protocols and areas of discomfort. I’ll forgive their missteps (an occupational hazard) if they land blows on deserving targets too. But that’s not really what’s happening on Chappelle’s specials: these aren’t missteps, this is a concentrated campaign. A philosophy, even – Chappelle seems to think that the struggle for sexual and gender equality is in competition with antiracism. As if civil rights is a zero-sum game, and the (relative, recent) headway made by trans activists represents a threat to Chappelle’s own cause.

The Netflix specials hint loudly at that. At one point, Chappelle expresses two opinions about trans people: one (positive) as an American, and one (sceptical) as a black American. At another, he rebukes a white woman for equating her (feminist) struggle with his (antiracist) one. But Chappelle has made the point more stridently since the specials were filmed. In a New York gig last autumn (the one where he seemed to defend Donald Trump’s “pussy-grabbing”), he reportedly scorned intersectionality (ie awareness that identity groups aren’t silos, but intersect with one another), arguing: “If you’re putting sexism and homophobia and transphobia in front of racism, you should be ashamed of yourself.”

If that’s what he believes – well, it’s a blinkered way of looking at things. It’s also won Chappelle some (presumably) unwelcome new admirers on the political right – and is making his comedy harder to love. There’s still plenty to enjoy about his two new Netflix specials, but there’s no denying that the (ex-)great man’s halo has come a bit loose since their release. On the third and final instalment, to be released later this year, rests more than just another $20m: Chappelle has a reputation to recover.