The goal of a stand-up comic is to both shock and amuse an audience. Many of the greatest stand-ups, from George Carlin and Richard Pryor to Eddie Murphy and Chris Rock, have developed long careers based on their brilliant, humourous takes on real-life issues.

Dave Chappelle’s case is an interesting one to consider. The 43-year-old comedian spent over a decade out of the spotlight after infamously walking away from a $50 million contract for his beloved Comedy Central series Chappelle’s Show. Now, he’s trying to make a comeback.

Following a hosting gig on Saturday Night Live last November, Chappelle signed a deal with Netflix worth $60 million to produce two stand-up specials, both of which premiered on March 21.

Although the specials seem to have been well-received among Chappelle’s fans, some of the jokes have landed him in hot water. Throughout the specials, Chappelle cracks jokes aimed at the LGBTQ+ community, and is receiving a swath of criticism in return.

This is not the first time the comedian has come under fire from the LGBTQ+ community. Shortly before the presidential election, he accused the LGBTQ+ community of stifling discussion of racism in America.

“They should not be having that conversation in front of black people,” Chappelle told a crowd during a performance in New York last November. “If you’re putting sexism and homophobia and transphobia in front of racism, you should be ashamed of yourself.”

Comedy, and stand-up in particular, is supposed to push the boundaries with regards to real-life issues. By finding humour in these serious issues, not only are we able to laugh at ourselves, but we’re able to start conversations about important issues.

Comedians like Chappelle have been hailed for doing just this. Many sketches from Chappelle’s Show both poked fun at and commented on racial issues, such as the Racial Draft sketch, or one sketch in which Chappelle played a blind white supremacist who is Black.

It seems that Chappelle has retained much of the comedic edge that made him popular to begin with. Why, then, do audiences seem more uncomfortable with his comedy now than they were 10 or 20 years ago?

The answer may be that the comedy audience has moved on to more progressive views, making Chappelle’s comedic style outdated. What audiences found shocking and hilarious about his material a decade or so ago, they now find shocking and offensive.

Chappelle should not be faulted for this, though, seeing as many comedians have a certain edge associated with their routine; toning it down would only hinder the creative process.

Yet during Chappelle’s hiatus, so much has changed in regards to the topics he frequently discusses in his comedy. The conversation surrounding feminism and LGBTQ+ rights has only gotten louder, and with Donald Trump’s presidency threatening much of the progress made during the earlier part of the decade, members of that group may feel legitimately threatened when someone cracks jokes about them.

Perhaps the greatest change to have occurred during Chappelle’s absence from the field of comedy was the emergence of social media, which played a role in the ascension of a new generation of comedians, including Aziz Ansari and Amy Schumer.

Performers such as Ansari and Schumer have struck a chord with fans due to their unique blend of observational humour and their willingness to advocate on behalf of feminism and LGBTQ+ rights.

If Chappelle wishes to be a part of the conversation by remaining a relevant and topical comedian, he should find a way to reassess his style. However, he should also make sure to keep his edge, as great stand-up comedy thrives on accompanying the audience into uncharted territory.