As sloshed septuagenarian lounge singer Kiki Durane of the Tony-nominated performance duo Kiki & Herb, Justin Bond earned international acclaim for his impassioned, intensely ironic covers of popular songs. Since retiring those Kiki wrinkles in February 2008, the 46-year-old Shortbus star has shifted to songwriting on the solo EP Pink Slip, arranged and conducted by fellow "trans-fabulous" songstress Our Lady J. Getting dolled up for a concert and release party July 22 at New York's Highline Ballroom, the self-proclaimed "performance-activist" talks to Advocate.com about transgender tribulations -- and how to stay as hip as Debbie Harry.

Advocate.com: You've been called just about everything in the media when it comes to descriptions of your sexuality, but I've gathered from reading your blog that you dislike such labels. If people are going to label you whether you like it or not, which label would you prefer?
Justin Bond: God, I think about that every day and I have the hardest time coming up with an answer. But I guess you can just call me a "trans-fabulous performance-activist."

Is the hyper-feminine self-portrait you created for the Pink Slip cover an idealized version of yourself?
That portrait was done based on a photo of me at the Drag March in New York maybe seven or eight years ago. It's not an idealized version of myself now, but it's a portrait of an idealized self I would've had as a teenager. It makes me think of that line from Grey Gardens: "You see me as a woman. I see myself as a little girl." [Laughs] When I was young I drew portraits of women all the time so that I could put makeup on them because I was forbidden to wear makeup. Once I was able to wear my own makeup, I stopped drawing for years and years. Now that I've taken it back up, I still think it's really more about the makeup than the drawing.

Is there an underlying theme running through Pink Slip?
I guess the four original songs come from my pagan queer world view, which is about placing value on nature and the nature of nature -- our nature as people and how we relate to each other. It's interesting to me how we relate to ourselves within the context of a world that's so full of material things. We're witnessing the decline of capitalism and trying to figure out where to place our energy, our focus, and our passion. That's really heavy, I guess. [Laughs] Basically, the themes are nature, love, and connectedness.

Why did you also cover "Weird Fishes" by Radiohead?
I love that song. I believe more in the Holy Spirit than in the Father and the Son. I think that our souls or spirits are energy, and our energies are essentially floating around when we're not incarnated into human form. But when we're in human form, our spirits are contained in these bodies that give us the opportunity to reach out and physically connect with other spirits. It's really abstract, but I think that's what that song is about. It's such a romantic notion that the only time you're ever able to physically connect with a beloved is when you're alive. That tangible connection is one of the greatest gifts of being alive, and that song expresses that idea so beautifully.

In addition to singing, your live shows are known for your witty yet thoughtful anecdotes and observations. Do you prepare topics in advance or is it a very "Jesus, take the wheel" situation?
It's a combination of both. I always think of my monologues as jazz; I have the theme and the outline, but then I just go off on variations, try new things, and see what happens. It makes it really fun. Sandra Bernhard does that, and that's why I love to see her perform repeatedly. If she's at Joe's Pub I'll go maybe three times so I can see how she changes her act each night, because it's so interesting to watch her work.

Is anything in current events worthy of a riff at your EP release concert?
The only thing I've been obsessing on is something I read recently about the treatment of trans and gay people in Iraq. The police there are rounding up homosexuals in Iraq and gluing their assholes shut with this very strong glue that's produced in Iran. Then they feed them some sort of food or medication that makes them have to shit. As they go to the hospital, a lot of times they're refused treatment because they're gay, so they die. This happened to, like, dozens of people in the past year and a half or something, and it has me so upset. I have to think of something funny or amusing because people don't want to hear about that, but I also feel compelled to mention it because it's the most horrible thing I've read in a long time. I was just interviewed by this woman in London who said something like, "Your work is very superficial fabulousness and camp haute couture, and yet I feel there's this level of deep emotion that surprises me." And I said, "Well, I don't think fabulousness and camp are superficial because people are being murdered around the world constantly for being fabulous and camp." Any type of feminine, outrageous, or unusual expression is basically license to kill.

You've always been very outspoken when it comes to transgender politics. You even criticized those you called "privileged white people" and "disgusting sell-out pigs" of the Human Rights Campaign in New York magazine. Do you feel like you're helping to mend the gap between the transgender and gay communities?
Maybe there's been progress, but I don't think assimilationist gay men see trans people as their advocates. It seems like they're always going to be at an impasse until they learn to love and respect each other's differences, but that's a lot harder for rigid people who think in linear terms. People who aspire toward mainstream normality have philosophies that are in lines, squares, rectangles, and boxes; other people's way of thinking is more circular. It doesn't have anything to do with your gender or sexual preference; it's just the way you are. It's like the difference between Democrats and Republicans: They just don't understand each other, and there's no way to bridge that divide. I don't know if it'll ever be great, but if you can't talk to someone to get them to do the right thing, you have to shame them into it. The HRC talks about how they're inclusive, and they put "T" on the end of things, but there's not one mention of trans people in any of their literature. The letter "T" makes it look like they're doing the right thing, when in fact they aren't, because they just don't care. And saying that they just don't care is actually being generous.

Does Chaz Bono have potential to bring positive visibility to the trans community?
I don't know if he should be their poster child, but if Chaz is male-identified, then there's no other question that needs to be asked. If that's the path he's on, it's our job to honor it. I don't know Chaz Bono, but you hear stories of butch lesbians who are having a hard time with all these other lesbians becoming men, and a lot of people think it's just about basic misogyny and an attempt to access male privilege. I've been lovers with FTMs, and it's true: They can pass and they do all of a sudden have access to male privilege. For them it's a great thing, so you can't blame them for enjoying that. It's a complicated issue, but good for Chaz for taking the steps.

Your release party is being hosted by 20-something performers Jeffery Self and Cole Escola, and you recently made a cameo as a nun on their Logo series, Jeffery & Cole Casserole. Because the LGBT community is so often divided by ageism, it's good to see collaboration between two generations. Are you teaching the children well and letting them lead the way?
I've talked about this with John Cameron Mitchell. People our age have lost a lot of our mentors to AIDS, so John and I both have made a conscious effort to try to connect with the younger generations of gays. I do it selfishly because I'm so inspired by them, but I'm also inspired by Debbie Harry, who's a generation older than me. She's still so active in the downtown art scene, she comes to see everyone's shows, and she showed up to do backup vocals when we did our Kiki & Herb record. I see how that's kept her young, relevant, and so intensely cool, so I want to be like that. I don't want to be one of those people who alienates themselves and becomes brittle. I like to keep young people around me to keep myself flexible and engaged. Many of these young, up-and-coming performers inspired me to feel that it was possible to make a career change right in the middle of my most productive years.

Speaking of the kids, proceeds from your concert will benefit the Ali Forney Center, a nonprofit organization dedicated to helping homeless LGBT youths.
What they're doing is so important because gays, lesbians, and trans -- especially trans -- have such high suicide rates. Even today, people are sending their children out on the street, or the children have suffered such terrible abuse that they had to leave home. Homelessness, teenage prostitution, and no education about safer sex are matters of life and death. Anything we can do to save some kid's life, provide a safe haven, and make them into a strong person is the most important thing that we can do as a community. It's an amazing thing to be a part of.

Tell me about your London show Justin Does Tragedy in London.
Well, the National Portrait Gallery is doing an exhibition called "ICONIC," and they've asked a bunch of famous homosexuals to choose icons and iconic images other than those in the National Portrait Gallery's collection. I chose Vivien Leigh because I was obsessed with Scarlett O'Hara and Blanche DuBois when I was a teenager. Vivien Leigh was one of the greatest English actresses, and she played two of the most iconographic American Southern roles. I guess the show's all about the ugly duckling aspiring to be a swan; many years later, the ugly duckling is sitting in a bar, talking about when he had been a swan. But was he ever really a swan? That's where the tragedy comes in. How many times can the Phoenix rise back out of the ashes before it goes, "You know what? I'm tired of this." I think that's what happened to Michael Jackson: He rallied and rallied, and then he couldn't do it again, so he just died.

Do you see yourself as a tragic figure?
No, not really, but I definitely could have potentially been one. All of the signposts were there pointing toward tragedy, but somehow, by sheer force of will, I've managed to avoid it thus far.