[2] She participated in LaChapelle's Artists and Prostitutes 1985–2005 exhibit in New York City, where she "lived" in a voyeuristic, life-sized set.

Realizing she was transgender from an early age, Lepore began sewing costumes for Bambi in exchange for female hormones.

In the early 1990s, Lepore intended to establish herself as an iconic nightlife figure (including becoming a key member of the Club Kids).

After meeting photographer David LaChapelle one evening, while hosting at Bowery Bar, she began collaborating with him and became a ‘muse’ of sorts for his work.

[11][13] Lepore has appeared in numerous pop culture and fashion publications, including French Playboy, Ponytail, DAMn and TUSH.

In 2016, Lepore had a major role in José André Sibaja's film The Zanctuary, where she played a drug dealer called Miss Divine.

Other cast members included Joey Arias and Sophia Lamar, with whom she also appeared in 2018 documentary I Hate New York from Spanish director Gustavo Sanchez.

Lepore has had cameos in music videos for artists including Elton John, Thalía, The Dandy Warhols, Girl in a Coma,[15] Grace Jones, Keanan Duffty, Sharon Needles, TIGA (for his cover of "Sunglasses at Night"),[16] and the alt rock band The Drums (for "Days").

Lepore's first single, "Deeper," was a 2003 trance dance song written by Wigstock drag queen Lady Bunny.

[20] The tour benefited the Human Rights Campaign, PFLAG and the Matthew Shepard Foundation, and it included Erasure, Debbie Harry, The Gossip, Rufus Wainwright, The Dresden Dolls, The MisShapes, Rosie O'Donnell, Indigo Girls, The Cliks, and other special guests.

[citation needed] In October 1999, Swatch released "Time Tranny", a watch designed by LaChapelle with Lepore on the face, which displays a printed crack on the glass and marble stripes as the background.

[24] In April 2006, Integrity Toys launched an Amanda Lepore doll produced by Jason Wu as a benefit for AIDS charities.