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During the 2020 pandemic quarantine Bond performed weekly House of Whimsy livestream concerts as Auntie Glam.

— Part of the fictional biography for Kiki and Herb.

Beginning in January 2014, Bond appeared alongside Stephen Spinella in the Classic Stage Company production of the Bertolt Brecht play, A Man's A Man (Man Equals Man), with new music by Duncan Sheik. The show ran Off-Broadway at the Company's theater on 13th Street in Manhattan's East Village, with Bond playing the part of Leokadia Begbick, a role originated by Brecht's wife, Helene Weigel. Bond left the show early to go abroad, premiering sold-out shows of Love is Crazy in Paris and New York. More performances are scheduled for London in February 2015.

In December 2014, Bond's wide range and appeal, as well as the personal struggles that have informed all of Bond's work, were once more on display in Star of Light! An Evening of Bi-Polar Witchy Wonder, which opened at Joe's Pub on Lafayette near Manhattan's Astor Place. One critic found in it "a surprisingly upbeat holiday show full of sad stories and songs" both eclectic and smartly executed, noting "a psychedelic intensity to Bond's voice reminiscent of Grace Slick of Jefferson Airplane." Backups included Matt Ray on piano, Claudia Chopek on violin, and NathAnn Carrera on guitar.

In the summer of 2014, Bond curated and emceed a cabaret season at the Spiegeltent at the Bard SummerScape Festival in the Hudson Valley, NY. Bond is set to reprise this emcee role in summer 2015, with guests including Alan Cumming, Suzanne Vega, Martha Wainwright, Stephen Merritt, and Lea Delaria.

Bond has decided to clarify an identity as a trans-person, explaining that "for me to claim to be either a man or a woman, feels like a lie. My identity falls somewhere in the middle and is constantly shifting." Bond undergoes hormone treatment to appear more feminine, and reported feeling great as a result, noting that "I like the way my body looks. Emotionally, it's evened me out." Eschewing gender reassignment surgery, Bond explained that "I like my penis, and I am keeping it, but I am creating a transbody—a physical record on my body and a medical record that I am a transgendered person." In 2011, Bond also adopted the middle name of 'Vivian', subsequently identifying as "Justin Vivian Bond" instead of "Justin Bond".

In concert at the end of 2014, Bond disclosed having received an invitation to return home for Thanksgiving, conditional upon leaving behind "that fake woman." Acknowledging that "a lot of trans-kids get kicked out of their homes," Bond mused "I didn't until I was 51. So I think I'm gonna make it." Elsewhere, Bond has said that "if it wasn't for my family and the rage they engendered in me, I wouldn't be here."

After graduation, Bond moved into the city to work briefly at Details magazine with Lumet. Returning to Maryland, Bond found roles in regional dinner theaters, often doubling as a server. This work led to a brief stint as assistant to the maitre d' of the Roof Terrace Restaurant in the John F. Kennedy Center for the Performing Arts, where Bond witnessed a memorable performance by Ella Fitzgerald. Bond took the job partly to find out "whether or not I could, if I had to, make a living in the 'straight' world" as a "normal, middle-class, semi-closeted gay..." According to Bond, this experiment provided the confidence to "plunge into my life as a gender non-conforming queer in San Francisco a year later believing that I could – in case of emergency – break the glass ceiling by returning to my closeted white male privilege again one day if need be." Bond moved to San Francisco in 1988.

Bond's new show, Mx America, was slated to open in Australia in February 2013.

In 2012, Bond toured nationally with lesbian-feminist, spoken-word collective Sister Spit. promoting the new album. Later that year, Bond opened the new holiday show, Snow Angel, with Amber Martin on vocals, NathAnn Carrera on guitar, and Brett Every on piano. Depending on the outcome of the presidential election, the name was intended to refer either to "the whimsical joy of making fun shapes in the snow," or "the imprint you would leave in the snow if you were being raped."

Bond starred as Warhol Superstar Jackie Curtis in Jukebox Jackie as part of the 50th anniversary season of La MaMa Experimental Theatre Club between May and June 2012. "I've always been really interested in Jackie, Holly Woodlawn, and Candy Darling," Bond recounted in an interview at the time, "because they, along with Renee Richards and Christine Jorgensen, were the first famous trans people. When I was young, they were really the only trans people to which I had been exposed." According to Bond, the project originated as a revival of one of Jackie's "crazy, amphetamine-fueled" plays, but Bond (and director Scott Wittman) "couldn't really make sense of them" and turned to reportage instead. "I always liked Jackie," Bond said, "because Jackie wasn't willing to say, 'I am a woman trapped in a man's body,' she'd say, 'I'm trans, I'm not a man. I'm not a woman. I'm Jackie.' Which, by the way, was the last line of the show."

Identifying as a queer performer infused Bond's art with an activist ethos from the beginning. In addition, Bond has labored tirelessly in support of queer causes and organizations and has been numbered "amongst New York City's most beloved performers . . . remarkable for their generosity of spirit..." Bond participated in the original Gay Shame event in New York in 1998, performing as Kiki and Herb and recorded in the Scott Berry documentary, Gay Shame '98. On September 25, 2012, Bond hosted a special edition of Weimar as a fundraiser for the reelection of U.S. President, Barack Obama. In November, Bond announced a performance to benefit the Ali Forney Center for LGBT youth in the wake of Hurricane Sandy. Ahead of the 2014 Olympics in Sochi, Bond appeared in a video by Brooklyn-based Potpourri of Pearls, protesting Russian mistreatment of LGBT persons.

In 2012, Bond announced the creation of a signature fragrance by Ralf Schwieger, a "trans-scent" for all genders called The Afternoon of a Faun after the French poem and modernist ballet of the same name, and issued under the French label Etat libre d'Orange. It was launched in February 2013, at Manhattan's Museum of Arts and Design on Columbus Circle.

Bond received a 2012 Lambda Literary Award for the memoir, Tango: My Childhood Backwards and in High Heels. Also in 2012, powerHouse Books released Susie Says, a picture book combining Gina Garan photos of the 1970s fashion doll, Susie Sad Eyes, with bon mots from Bond's Twitter account.

2011 saw the opening of The Fall of the House of Whimsy exhibition at Participant, Inc., an alternative, Manhattan gallery that hosted an installation of "artifacts, media, and ephemera" from Bond's nearby loft (then slated for demolition) including original Bond photographs and watercolors. The "spectral" photographs reflected mostly unoccupied interiors of the loft, while the paintings, portraits and self-portraits, have been described as "light, aerie images," whose subjects fade in and out. Also on display was a music video of the Bond composition, American Wedding.

Justin Bond: Christmas Spells opened in December 2010 at Abrons Arts Center on Grand Street in Manhattan's Lower East Side. The two-part show included a trademark cabaret performance of holiday tunes, showcasing an original composition, Could Baby Jesus in His Manger Foresee the Hate Sprung From That Night? This was followed by a theatrical adaptation of a short story by a Bond pal, the artist and gender-theorist Kate Bornstein. Dixie Belle: The Further Adventures of Huckleberry Finn, was conceived as a holiday epistle informing Tom Sawyer of the author's gender-bending adventures in a New Orleans bordello after the Civil War. The letter was read by Bond and enacted by the drag troupe Pixie Harlots. In December 2015 an EP also called Christmas Spells was released including 3 songs (Have Yourself a Merry Little Christmas, Remember (Christmas) and Christmas Spells).

The EP and the two albums that followed likewise appear to have arisen rather spontaneously, differing largely in terms of the original material they contained as a result of Bond's decision to venture into songwriting. Wanting to get something out quickly and not sure how to do it, Bond released a five track EP Pink Slip in June 2009 featuring four original songs ("The New Depression," "May Queen," "The Puppet Song," "Michael in Blue") and a cover of Radiohead's "Arpeggi/Weird Fishes". Pink Slip was recorded at Le Poisson Rouge and Bond hoped income from the EP would help fund the recording of an album. Both of the albums were self-financed, and both were the result of a collaboration with pianist/producer Thomas Bartlett of the band Doveman. The first, Dendrophile (2011), contained a mix of original compositions and covers modeled on a type of "early-'70s folk-pop variety album" in the spirit of Judy Collins, featuring a duet with English singer-songwriter Beth Orton. The title apparently references the creative energy arising from self-acceptance, and is "all about honoring your nature, and nature itself." Bond used Kickstarter to finance the release of a second album, Silver Wells, in 2012. The album was conceived as an homage to the 1970 Joan Didion novel, Play it as it Lays, which fortified Bond against the isolation that Bond experienced as a child. The album features covers of songs made famous by Ronee Blakley, Kate Bush, Leonard Cohen, Tracy Chapman, Joni Mitchell, Mark Eitzel, Bertolt Brecht and Kurt Weill, among others, and has been described as "intimate" and "confessional" in tone. Bond put the songs together as a set list for a show, only later deciding to go into the studio with Bartlett.

In July 2009 Bond made an appearance on the Logo TV comedy series Jeffery & Cole Casserole, playing a Catholic nun who serves as the principal of the show's all-girl Catholic school.

Bond's solo career as a singer, emcee, cabaret artist, and actor, grew up alongside Kiki and Herb, and ultimately outlived them. Prior to retiring Kiki in 2008, Bond already was touring nationally and abroad, appearing in film, and recording under the name of Justin Bond. Post-Kiki, Bond continued to move freely between San Francisco and New York, frequently traveling to London and less frequently, to Australia. The period that followed differed largely in terms of the originality and variety of material as Bond experimented with new endeavors.

In 2008, the GLAAD-nominated show Lustre premiered at PS122 in the East Village to rave reviews before touring the UK with stops in London and Manchester as part of the It's Queer Up North Arts Festival. In December 2008, Bond appeared at London's Southbank Centre as Sinderella, in the original musical written by Martyn Jacques of the British cult trio Tiger Lillies. Bond was credited in the band's album of the same name. Bond has appeared with Carol Channing, Tilda Swinton, and Chocolate Genius, Inc., among others.

The musician Rufus Wainwright, son of Canadian folk singer Kate McGarrigle, was another rising star from the downtown club scene who befriended Bond at this time. In 2008, Bond participated in a Christmas show at the Knitting Factory that included Rufus Wainwright, members of Wainwright's family, Grammy Award-winner Emmylou Harris, Lou Reed, Velvet Underground, and performance artist Laurie Anderson. Revelation Films released the concert DVD in November 2009 under the title A Not So Silent Night (Kate & Anna McGarrigle/Rufus & Martha Wainwright). Bond has appeared in concert with Rufus Wainwright's sister, Martha Wainwright, whom Bond calls a "Taurean sister." In 2011, Bond stated that "we are going to celebrate our birthdays together this year." In May of that year, Bond appeared with various artists in "A Celebration of Kate McGarrigle," at New York City's Town Hall, to commemorate the passing of the Wainwrights' mother, who had succumbed to cancer the previous year. A DVD was released in 2013. In August 2012, Bond officiated at Rufus Wainwright's Long Island wedding.

After closing on Broadway, Bond took a brief hiatus in London to get away from Kiki, before returning later that year in preparation for the final, American tour. This was followed by a return to Carnegie Hall for a one-night show on December 12, 2007, billed as Kiki and Herb: The Second Coming – A Christmas Concert. The show played again at the Shepherd's Bush Empire in London. In spite of their retirement, Kiki and Herb appeared on a list of the top 40 favorite New Yorkers in Time Out New York in 2008. In a 2011 interview with The Guardian, Bond quipped that Kiki DuRane, if not actually deceased, was at least "in a nursing home in New Jersey."

Bond has hosted the Weimer New York variety show since its inception in 2007. Justin Bond is Close To You reinterpreted Karen Carpenter's album Close To You as part of Joe's Pub in the Park in Central Park in 2007, later moving to Australia's Sydney Opera House.

Their show Kiki & Herb: Alive on Broadway ran for five weeks in 2006, and was nominated for a 2007 Tony for Special Theatrical Event. One critic noted that onstage they are "Alive with a capital A, with all the human vitality and fallibility that that implies." A poster on tribe.net reported hearing them mentioned on an episode of Will and Grace early in 2006, noting that "now they have crossed over." Ironically, Bond was by then moving away from the stage act after more than a decade, having almost come to resent the "very intrusive" presence of Kiki and the demands associated with playing this "very dark" role. "I knew that if I kept doing Kiki I wouldn't have the energy to focus on what I really wanted to do," Bond explains, "which was write and perform as myself." "I created an invulnerable character in Kiki," Bond reflected elsewhere, "and as soon as I got rid of the character, there were a lot of bad habits that sort of fell away. I realized that I have to allow myself to be more vulnerable, more honest, if I'm going to be a performer." Locked into a stage act consisting of one other person, it appears that Bond had also begun to feel socially constrained.

In June 2006, Bond appeared with David Hoyle in a one-off entitled When David Met Justin at London's Bush Hall. Performing with the House of Whimsy Players at The Kitchen in October, Bond staged Re:Galli Blond (A Sissy Fix), "a self-penned musical spectacle of transgender oppression and uplift." Bond also appeared in Paul Festa's Apparition of the Eternal Church (2006).

In 2006, Bond appeared in the film Shortbus, as part of cast that included Sook-Yin Lee, PJ DeBoy, and Paul Dawson. In the movie, directed by fellow Radical Faerie John Cameron Mitchell, Bond played the mistress of ceremonies at the eponymous avant-garde salon Shortbus, singing the Scott Matthew number, "In the End," to the music of the Hungry March Band. One journalist commented that this expressed "in just one scene that heightened sense of simultaneous hope and despair in post–9/11 downtown New York City." Bond referred to the film as a "gorgeous little time capsule."

The duo traveled repeatedly to London, where Bond continued to work on an MA in scenography at Central St. Martin's College of Art and Design when not performing. London shows included Where Are We Now?, Kiki & Herb: There's a Stranger in the Manger, and Kiki & Herb Mount The President, the latter performed aboard HMS President in the River Thames. Bond had a Top 20 Single on the UK alternative chart and was named one of England's fifty funniest people by Time Out London. The mockumentaries entitled Kiki and Herb on the Rocks (2005) and Kiki and Herb Reloaded (2005) followed the pair to London and around the UK, respectively, featuring the composer Philip Glass, among others.

Jake Shears, lead singer of Scissor Sisters, has cited the Kiki and Herb Christmas Show as inspiration. Bond and Shears became friends, with the Scissor Sisters fronting for Kiki and Herb at The Knitting Factory, and with Bond later returning the favor after the band's eponymous debut album went platinum in the United Kingdom in 2004. Bond appeared in the 2017 Music Box Theatre performance of the Tales of the City musical, with score by Shears.

Kiki and Herb met with more critical acclaim with each successive appearance and developed a cult following. They received their first New York Times review for Have Another, (1999), a show that earned a GLAAD media award the following year. They performed extensively, namely in London's Soho Theatre and Queen Elizabeth Hall and New York's The Knitting Factory and Carnegie Hall, as well as a host of other venues worldwide. Their numerous collaborators included Debbie Harry of Blondie, comedian Sandra Bernhard, and Antony of Antony and the Johnsons. Their recordings included the Christmas album, Do You Hear What We Hear? (2000), and Kiki and Herb Will Die for You: Live at Carnegie Hall (2005). In 2004, Bond and Mellman did a cameo in the Sony Pictures release Imaginary Heroes, with script by Dan Harris. Appearing alongside Sigourney Weaver, Jeff Daniels, and Emile Hirsch, the duo reprised the Melanie Safka composition Tonight's the Kind of Night from Do You Hear What We Hear? Their stage act was captured on video in Kiki and Herb Live at the Knitting Factory (2007). They toured twice in the U.S., including the 2007 'Year of Magical Drinking Tour.'

Bond was namechecked in the 1999 Le Tigre song "Hot Topic" from the band's eponymous debut album.

Bond's first album came about unexpectedly, as the result of an improvised concert with experimental, electronic sound artist Bob Ostertag and a Japanese turntablist from the Tokyo noise underground, Otomo Yoshihide, at San Francisco's Great American Music Hall in 1997. Bond already appeared on two tracks ("Not Your Girl" and "The Man In The Blue Slip") on Ostertag's 1995 album, "Fear No Love", sharing co-lead vocals duties with Mike Patton. Other guests on the record were Fred Frith and Lynn Breedlove. At the behest of the record label Asphodel, an album was recorded in this location and in studio at Toast, with additional tracks and musicians added later. Since Otomo spoke little English and could not understand what Bond was saying, he watched the recording engineer through the glass and "when I see he laugh, I play something funny." The album was ultimately released under the Seeland label in 1999 as PantyChrist, with a European, promotional tour. Although it failed commercially, Ostertag viewed it from an artistic standpoint as "one of my most successful projects."

Bond moved to New York City in 1994, in the midst of crackdown on queer clubs by then-mayor Rudy Giuliani. A quote from Bond relates that "I worked in many bars where the police would just come and shut us down and throw us all out on the street at two or three in the morning." Nevertheless, the act continued to evolve, generating a mythical backstory as the entertainers became "fixtures at downtown New York venues like Flamingo East, P.S. 122, and Fez." Journalist John Russell saw in Kiki "an icon to rival Hedwig." The New York Times has dubbed Kiki "the town's most endearingly unhinged chanteuse," comparing Bond favorably to more conventional performers for whom "the point is never the prettiness of the voice." Bond has said that "I think that the reason people liked Kiki so much is that she had just about everything wrong with her."

A turning point occurred when Kate Bornstein cast Bond in her new play, Hidden: A Gender, using the life of the French, intersex person Herculine Barbin as an autobiographical device. Bond "was not sure he could really pull off playing a girl," according to Bornstein, and feared the censure of "his gay male friends." In fact, the experience unleashed a reservoir of creative energy. With the assistance of a twenty-something Berkeley drop-out named Kenny Mellman, Bond created the award-nominated lounge act Dixie McCall's Patterns for Living around the persona of actress and singer Julie London. The duo played a number of gigs, both in and out of character; three years after attending Pride for the first time, Bond was hosting the show at the end of the parade. In 1993, Bond hosted the first San Francisco Drag King Contest at the DNA Lounge with Elvis Herselvis. In 1994, Bond appeared on film for the first time, as Amphetamine in John Moritsugu's Mod Fuck Explosion, and again the following year in Fanci's Persuasion.

Bond remembers this as a period of significant personal growth, both creative and political. It was here that Bond turned androgyny into a professional asset, developing an identity as a queer performer and activist. The first steps on this journey led through the Castro District, the vibrant, queer neighborhood mostly concentrated on Castro Street between Market and 19th in San Francisco. Bond started out broke, clerking in a gay bookstore to buy the coffee at Cafe Flore on Market and Noe, a bohemian salon that became a "spiritual home." Seated at the "Queen's Table" in the corner, Bond absorbed a variety of perspectives from all corners of the LGBT community, attending Gay Pride for the first time in 1989. Participation in Queer Nation and ACT UP, advocacy groups combatting HIV/AIDS, anti-gay violence, and media prejudice, gave Bond "a voice and a sort of grounding in politics" that were new. At some point, Bond adopted the stage name of Justin, later explaining that there were few fates worse than becoming an old, gay man named Chip.

Bond studied theater at Adelphi University on Long Island from 1981 to 1985. The newly minted freshman saw Simon and Garfunkel in concert in Central Park, but it was visiting Carnegie Hall for the first time to see Judy Collins that invoked the realization that "I had escaped my hometown and was finally beginning to live the life I'd dreamed of." Bond went to London to study theater in the summer of 1984, befriending fellow student Victoria Leacock, daughter of the filmmaker, Richard Leacock. Leacock knew Jenny Lumet, a granddaughter of Lena Horne, and managed to get Bond backstage to meet Horne, who appeared "icy, intimidating, beautiful and talented – everything I hoped to be one day." Bond later sported a pair of Horne earrings as a souvenir. Meanwhile, Adelphi advised Bond to become more "butch" to earn a living in soap operas.

Justin Vivian Bond (born May 9, 1963) is an American singer-songwriter, author, painter, performance artist, and actor. Described as "the best cabaret artist of their generation" and a "tornado of art and activism," Bond first achieved prominence under the pseudonym of Kiki DuRane in the stage duo Kiki and Herb, an act born out of a collaboration with long-time co-star Kenny Mellman. With a musical voice self-described as "kind of woody and full with a lot of vibration," Bond is a Tony-nominated (2007) performer who has received GLAAD (2000), Obie (2001), Bessie (2004), Ethyl (2007), and a Foundation for Contemporary Arts Grants to Artists (2012) awards. Bond is transgender and prefers the gender-inclusive honorific Mx. (in place of Ms./Mr.) and pronoun v (with vself instead of her/himself), a reference to Bond's middle name.