With a musical voice self-described as "kind of woody and full with a lot of vibration",[4] 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.

[7] They 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.

[10] A turning point occurred when Kate Bornstein cast Bond in her play Hidden: A Gender, using the life of the French, intersex person Herculine Barbin as an autobiographical device.

"[11] With the assistance of Kenny Mellman, they created the lounge act Dixie McCall's Patterns for Living around the persona of actress and singer Julie London.

[12] 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.

Bond is best known for originating the role of washed-up lounge singer Kiki DuRane, "an alcoholic battle-axe with a throat full of razor-blades.

"[20] The New York Times called Kiki "the town's most endearingly unhinged chanteuse",[21] comparing Bond favorably to more conventional performers for whom "the point is never the prettiness of the voice.

'[27] 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.

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.

Bond's first album was 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.

They 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.

[36] The first, Dendrophile (2011), contained a mix of original compositions and covers modeled on a type of "early-'70s folk-pop variety album"[36] in the spirit of Judy Collins, featuring a duet with English singer-songwriter Beth Orton.

[38] 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.

In 2008, the GLAAD-nominated show Lustre premiered at PS122 in the East Village, then toured the UK with stops in London and Manchester as part of the It's Queer Up North Arts Festival.

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?

"I've always been really interested in Jackie, Holly Woodlawn, and Candy Darling," they recounted in an interview at the time, "because they, along with Renée Richards and Christine Jorgensen, were the first famous trans people.

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.

[19] In the movie, directed by fellow Radical Faerie John Cameron Mitchell, they 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.

Revelation Films released the concert DVD in November 2009 under the title A Not So Silent Night (Kate & Anna McGarrigle/Rufus & Martha Wainwright).

[47] In May 2011, they 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.

In November, Bond announced a performance to benefit the Ali Forney Center for LGBT youth in the wake of Hurricane Sandy.

[49] Ahead of the 2014 Olympics in Sochi, they appeared in a video by Brooklyn-based Potpourri of Pearls, protesting Russian mistreatment of LGBT persons.

[52] In the summer of 2014, Bond curated and emceed a cabaret season at the Spiegeltent at the Bard SummerScape Festival in the Hudson Valley, New York.

They are set to reprise this emcee role in summer 2015, with guests including Alan Cumming, Suzanne Vega, Martha Wainwright, Stephen Merritt, and Lea Delaria.

[53] In July 2020 Bond was announced as part of the cast of Audible's adaptation of Neil Gaiman's The Sandman series, playing the role of Desire of the Endless.

[56] 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."