[6][7] Crary served on the jury of the 2005 Tribeca Film Festival alongside Alan Cumming, Whoopi Goldberg, Darren Arronofsky, Tom Wolfe, Damon Dash, Jeff Bezos, and others.

William S. Burroughs: A Man Within premiered at the 2010 Slamdance Film Festival and was acquired for distribution in North America by Oscilloscope Laboratories, in Australia by Madman Entertainment, in Germany by Neue Visionen, and in France by Arte.

[16][17] The film features interviews with Bruce LaBruce, Kathleen Hanna, Kim Gordon, Rick Castro, John Waters, Peaches, Dennis Cooper, and others.

[32] The film, entitled Elvis From Hell, will feature original interviews with Nick Cave, Debbie Harry, Mick Harvey, Jim Jarmusch, Mark Lanegan, Moby, Kid Congo Powers, Jack White, and others.

[45] In 2005, Sight & Sound's Stephen Dalton characterized Crary's experimental video pieces as "short meditative loops" that "often deliver a kōan-like punchline.

[48] On April 16, 2015, Crary previewed selections from a forthcoming conceptual photo book which depicts the former New York City residences of celebrated creative personalities, such as Jean-Michel Basquiat, William S. Burroughs, Diane Arbus, Bob Dylan, J.D.

[49][50] Although more significantly known for his subsequent film work, Crary at first came to public attention in the mid to late 1990s as a hip-hop turntabilist, mixtape deejay and occasional producer, using the stage name DJ S.T.R.E.S.S.

During this time, he performed as a supporting act on tours for such artists as De La Soul, Jungle Brothers, Smif-n-Wessun, Heltah Skeltah, and Chuck D of Public Enemy.

[51] He also released a number of self-produced mixtapes, which are notable for featuring some of the earliest appearances of artists like El-P, Mos Def, and Eminem, as well as original freestyles by The Roots, KRS-One, and Jeru The Damaja.

In April 2012, artist Seth Kim-Cohen used Crary's film Kill Your Idols as a basis for his solo exhibition, Tomorrow Is The Question?

[66] In 2016, Crary was included in the book Downtown Manhattan 78-82: De la No Wave aux Dancefloors, published in France by Le Texte Vivant.