Chan's work concerns topics including geopolitics, globalization, and their responding political climates, war documentation, violence, deviance, and pornography, language, and new media.

[3] Chan's essays and interviews have appeared in Artforum, Frieze, Flash Art, October, Tate, Parkett, Texte Zur Kunst, Bomb, and other magazines and journals.

Hong Kong's air quality had a deleterious effect on Chan's health, so his family relocated to Sioux City, Iowa in 1980, and later moved to Omaha, Nebraska.

[5] One such project was Alternumerics (2000), a series of fonts available for use on Macs and PCs that transform what the user types into both legible and illegible blocks of text that explore both the "relationship between language and interactivity" and the "fissure between what we write and what we mean.

[8] Following a 2002 trip to Iraq with the anti-war activists Voices in the Wilderness, Chan's work became increasingly concerned with war and politics.

Chan gathered Re: The Operation, Baghdad in no Particular Order, and Now Promise Now Threat into a single collection he named The Tin Drum Trilogy.

[10] It was there that he premiered My Birds...Trash...The Future (2004), a 17-minute two-channel animation featuring characters based on murder victims Pier Paolo Pasolini and Biggie Smalls adrift in a bleak landscape populated by a lone tree, birds from the Biblical book of Leviticus, hunters, and paparazzi in yellow Hummers.

The audio for the animation was broadcast from the muzzle of a toy gun that required viewers to lift it to one of their ears in order to hear it.

In a formal break with his previous animations, Chan designed 7 Lights to be projected on the walls and floor of its venue, instead of on a rectangular screen.

[6] He started a "shadow fund" with Creative Time that matched the production cost of the play and was later donated to organizations in New Orleans involved in post-Katrina recovery.

[16] Parallels were drawn by critics between the violent sexual orgies depicted in Sade and the abuse of prisoners at Abu Ghraib.

In a return to his earlier Alternumerics project, Chan produced a collection of fonts based on the writings of Marquis de Sade.

A carrot is a stick.”[19] Badlands Unlimited has since published over 50 paper books, e-books, and artist editions, including works of Etel Adnan, Cory Arcangel, Bernadette Corporation, Ian Cheng, Petra Cortright, Aruna D’Souza, Marcel Duchamp, Carroll Dunham, Claudia La Rocco, Hans Ulrich Obrist, Craig Owens, Yvonne Rainer, Rachel Rose, Dread Scott, Cauleen Smith, Martine Syms, Lynne Tillman, and Calvin Tomkins.

Chan ended his hiatus in April 2014 with the opening of the six-month-long show "Selected Works" in Schaulager, Basel.

Chan calls these new works “Breathers.” Each Breather consists of a fabric shell attached to one or more specially modified fans.

According to Chan, he employs techniques from fashion design, physics, and other fields to influence how the air flows from the fans to create different kinds of motion.

I wanted to control the movement of these works as nimbly as I could control the animations when I was working on a computer.”[22][23][24] In 2018, Chan collaborated with the Greek-based non profit organization NEON to present Odysseus and the Bathers, an exhibition curated by Sam Thorne, Director of Nottingham Contemporary at the Museum of Cycladic Art in Athens, Greece.

From 2002 to 2006, Chan was part of an American aid and activist group that opposed the US-led invasions and is called Voices in the Wilderness, and he worked in Baghdad in 2002.

[45] Artists Emilie Clark and Lytle Shaw were arrested for a "quality of life infraction" for taping a photo to a metal lamppost.

In 2004, Chan collaborated with Josh Breitbart, Nadxi Mannello, and Elise Gardella to create A People's Guide to The Republican National Convention (2004).