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Dave Chappelle reportedly still telling transphobic jokes

the comedian makes controversial commentary on trans people in the military, Caitlyn Jenner

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(Screenshot via YouTube.)

Comedian Dave Chappelle, known for his controversial social commentary, is coming under fire for telling transphobic jokes in his recent stand-up show.

The 43-year-old D.C. native kicked off a 16-show run at Radio City Music Hall in New York City. Jesse David Fox of Vulture wrote a report of the show and said Chappelle began his show with 20-minutes of transgender jokes.

“He started by talking about how he was ‘shocked!’ by Trump’s ban on transgender officers in the military, because he didn’t realize there were any trans people in the military. ‘Sounds like a secret weapon to me,’ he continued. ‘If I was in ISIS in the trenches fighting against the United States and all of the sudden I see a man with a beard and big D-cups titties just rushing my foxhole and shit, I’d be horrified,'” Fox writes.

Fox went on that Chappelle appeared to show some remorse for his jokes but only continued to make more transphobic jokes.

“Later, he told a story about receiving a fan letter that derided his trans jokes, to which he replied, ‘A weird thing happened to me in this moment — it honestly made me feel bad that I made somebody else feel bad.’ That was, however, just misdirection for another series of trans jokes,” Fox continued.

Chappelle also opted for a Caitlyn Jenner joke, making fun of the former Olympian appearing in Sports Illustrated.

“‘I read in the paper that Caitlyn Jenner was contemplating posing nude in an upcoming issue of Sports Illustrated. And I knew it was politically incorrect to say, so I figured I’d just say it for everybody — yuck. Fuck, man, I just want to read some stats, like why are you cramming man-pu*sy in the middle of the sports page like that?'” Fox writes.

Chappelle also joked that the only reason transgender issues have come to the forefront is because of race.

“He then tried to make a fairly complicated point about his own frustration with ‘all this talk about how they feel inside,’ because ‘since when has America given a fuck about how anyone feels inside?’ He ended by arguing that sometimes he thinks ‘the only reason all of us are talking about transgenders is because white men want to do it. If it was just blacks and Mexican like, ‘Hey, y’all, we feel like girls inside.’ They’d be like, ‘Shut up, nigger, no one asked how you felt,'” Fox writes.

Chappelle’s latest stand-up shows have been heavily saturated with transgender jokes. In one of his Netflix specials, Chappelle also made controversial LGBT jokes and called out LGBT activists for slamming his shows.

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Photos

PHOTOS: WorldPride Street Festival and Closing Concert

Doechii, Khalid among performers

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Doechii performs at the WorldPride Closing Concert on Sunday, June 8. (Washington Blade photo by Michael Key)

WorldPride 2025 concluded with the WorldPride Street Festival and Closing Concert held along Pennsylvania Ave., N.W. on Sunday, June 8. Performers on the main stage included Doechii, Khalid, Courtney Act, Parker Matthews, 2AM Ricky, Suzie Toot, MkX and Brooke Eden.

(Washington Blade photos by Michael Key)

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PHOTOS: WorldPride Parade

Thousands march for LGBTQ rights

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The 2025 WorldPride Parade (Washington Blade photo by Michael Key)

The 2025 WorldPride Parade was held in Washington, D.C. on Saturday, June 7. Laverne Cox and Renée Rapp were the grand marshals. 

(Washington Blade photos by Michael Key and Robert Rapanut)

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Theater

A hilarious ‘Twelfth Night’ at Folger full of ‘elegant kink’

Nonbinary actor Alyssa Keegan stars as Duke Orsino

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Alyssa Keegan (Photo courtesy Folger Theatre)

‘Twelfth Night’
Through June 22
Folger Theatre
201 East Capitol St., S.E.
$20-$84
Folger.edu

Nonbinary actor Alyssa Keegan (they/them)loves tapping into the multitudes within. 

Currently Keegan plays the melancholic Duke Orsino in Folger Theatre’s production of Shakespeare’s romantic comedy “Twelfth Night.” Director Mei Ann Teo describes the production as “sexy, hilarious, and devastating” and full of “elegant kink.” 

Washington-based, Keegan enjoys a busy and celebrated career. Her vast biography includes Come From Away at Ford’s Theatre; Cat on a Hot Tin Roof (Helen Hayes Award, Best Actress) and Paula Vogel’s How I Learned to Drive, both at Round House Theatre; Diana Son’s Stop Kiss directedby Holly Twyford for No Rules Theatre Company; and Contractions at Studio Theatre, to name just a few. 

In addition to acting, Keegan works as a polyamory and ethical non-monogamy life and relationship coach, an area of interest that grew out of personal exploration. For them, coaching seems to work hand in hand with acting. 

WASHINGTON BLADE: You’re playing the lovesick Orsino in Twelfth Night. How did that come about? 

ALYSSA KEEGAN: The director was looking to cast a group of actors with diverse identities; throughout auditions, there were no constraints regarding anyone’s assigned sex at birth. It was really a free for all. 

BLADE: What’s your approach to the fetching, cod-piece clad nobleman?

KEEGAN: Offstage I identify as completely nonbinary; I love riding in this neutral middle space. But I also love cosplay. The ability to do that in the play gives me permission to dive completely into maleness. 

So, when I made that decision to play Orsino as a bio male, suddenly the part really cracked open for me. I began looking for clues about his thoughts and opinions about things like his past relationships and his decision not to date older women.

Underneath his mask of bravura and sexuality, and his firmness of feelings, he’s quite lonely and has never really felt loved. It makes sense to me why his love for Olivia is so misguided and why he might fall in love with the Cesario/Viola character.

BLADE: As an actor, do you ever risk taking on the feelings of your characters? 

KEEGAN: Prior to my mental health education, yes, and that could be toxic for me. I’ve since learned that the nervous system can’t tell the difference between real emotional distress and a that of a fully embodied character. 

So, I created and share the Empowered Performer Project. [a holistic approach to performance that emphasizes the mental and emotional well-being of performing artists]. It utilizes somatic tools that help enormously when stepping into a character. 

BLADE: Has changing the way you work affected your performances?

KEEGAN: I think I’m much better now. I used to have nearly debilitating stage fright. I’d spend all day dreading going onstage. I thought that was just part of the job. Now, I’ve learned to talk to my body. Prior to a performance, I can now spend my offstage time calmly gardening, working with my mental health clients, or playing with my kid. I’m just present in my life in a different way. 

BLADE: Is Orsino your first time playing a male role?

KEEGAN: No. In fact, the very first time I played a male role was at the American Shakespeare Center in Staunton, Va. I played Hipolito in Thomas Middleton’s The Revenger’s Tragedy. 

As Hipolito, I felt utterly male in the moment, so much so that I had audience members see me later after the show and they were surprised that I was female. They thought I was a young guy in the role. There’s something very powerful in that.

BLADE: Do you have a favorite part? Male or female? 

KEEGAN: That’s tough but I think it’s Maggie the Cat. I played the hyper-female Maggie in Tennessee Williams’ Cat on a Hot Tin Roof at Round House. In the first act she didn’t stop talking for 51 minutes opposite Gregory Wooddell as Brick who barely had to speak. That lift was probably the heaviest I’ve ever been asked to do in acting. 

BLADE: What about Folger’s Twelfth Night might be especially appealing to queer audiences?

KEEGAN: First and foremost is presentation. 99% of the cast identify as queer in some way. 

The approach to Shakespeare’s text is one of the most bold and playful that I have ever seen.  It’s unabashedly queer. The actors are here to celebrate and be loud and colorful and to advocate. It’s a powerful production, especially to do so close to the Capitol building, and that’s not lost on any of us.

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