He has shot advertising campaigns for Marc Jacobs, Aldo, Supreme, Sisley, Tom Ford, and Yves Saint Laurent among others, and also done work for magazines such as Rolling Stone, GQ, Vogue, Vanity Fair, Harper's Bazaar, i-D, and Vice.

[11] Following the divorce of his parents, Richardson moved to Woodstock, New York, with his mother and stepfather, English guitarist Jackie Lomax.

[14] He played bass for a variety of other punk bands in Southern California including Signal Street Alcoholics, Doggy Style, Baby Fist and Middle Finger.

[8][15] Richardson's mother reportedly gave him his first snapshot camera in 1982,[13] which he used to document his life and the punk rock scene in Ojai.

[13] In 1992, Richardson quit music and moved to the East Village neighborhood of New York City, where he began photographing young people partying and other nightlife.

[15] Following the showing, Richardson shot an advertising campaign for fashion designer Katharine Hamnett's spring 1995 collection.

[15][16] The campaign was noted for images of young women wearing short skirts with their pubic hair showing.

[16] Throughout his career, Richardson has shot the campaigns of fashion brands and designers such as: Marc Jacobs, Aldo, Supreme, Sisley, Tom Ford, and Yves Saint Laurent.

[21] In May 2012, a video of model Kate Upton performing the Cat Daddy dance for Richardson in his studio went viral.

[25] Richardson's "Feared by Men Desired by Women" was shown at an exhibition at London's Shine Gallery the following year.

[28] Mom + Dad, a show exhibiting work from Richardson's book of the same name, was held at Half Gallery in New York City in 2011.

In late 2013 Richardson did the treatment on the music video for "Do What U Want" by Lady Gaga and R. Kelly from her third studio album titled Artpop, but the film was never released.

On August 21, 2017, Richardson directed the Anitta music video, "Vai Malandra", at Vidigal, Rio de Janeiro.

There are several repeating themes in Richardson's work, notably that of putting high-profile celebrities in mundane situations and photographing them using traditionally pedestrian methods, such as the use of an instant camera.

[39] Richardson counts Larry Clark, Nan Goldin, Diane Arbus and Robert Frank as early influences on his artistic style.