Richardson was born in New York City, the son of Norma Kessler, an actress, and Bob Richardson, a fashion photographer who struggled with schizophrenia and drug abuse. Following the divorce of his parents, Richardson moved to Woodstock, New York, with his mother and step-father, Jackie Lomax. Richardson later moved to the Hollywood neighborhood of Los Angeles, where he attended Hollywood High School. He moved with his mother to Ojai, California, where he attended Nordhoff High School, when he was 16. Richardson originally wanted to be a punk rock musician rather than a photographer. He played bass guitar in the punk rock band The Invisible Government for four years. He played bass for a variety of other punk bands in Southern California including Signal Street Alcoholics (SSA), Doggy Style, Baby Fist and Middle Finger.
His mother reportedly gave Richardson his first snapshot camera in 1982. He used the camera to document his life and the punk rock scene in Ojai. In 1992, Richardson quit music and moved to the East Village neighborhood of New York City, where he began shooting scenes of young people partying and New York City's nightlife. It was in New York City that Richardson had his first "big break." His first published fashion photos appeared in Vibe in 1994. His Vibe spread was shown at Paris's International Festival de la Mode later that year. Following the showing, Richardson shot an advertising campaign for fashion designer Katharine Hamnett's spring 1995 collection. The campaign was noted for images of young women wearing short skirts with their pubic hair showing.
Richardson moved to London, England, following the Katharine Hamnett advertising campaign. In London he worked for European magazines such as The Face, i-D and Arena.
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. He has done work for magazines such as Rolling Stone, GQ, Vogue, Vanity Fair, Harper's Bazaar, i-D, and Vice.
Richardson has produced several campaigns for Diesel, including the 'Global Warming Ready' which won a Silver Lion for Print at Cannes Lions International Advertising Festival in 2007. Throughout the years he has also produced several private portraits for the company's founder, Renzo Rosso. In September 2011, they hosted a mutual book launch together with fashion editor Carine Roitfeld, at Colette in Paris.
In 2012 Richardson embarked on his first solo exhibition at Los Angeles's OHWOW Gallery. The exhibition was titled "TERRYWOOD" and ran from February 24 to March 31, 2012. In May 2012, a video of model Kate Upton performing the Cat Daddy dance for Richardson in his studio went viral. In December 2012, Lady Gaga announced that Richardson was filming a documentary about her life. Vice co-founder Gavin McInnes defended Richardson in 2004, saying his work was criticized by "first-year feminist types."
Richardson has been accused several times of using his influence to coerce models to engage in undesired sexual behaviors and poses during fashion shoots, including engaging in sexual acts with Richardson himself. Some models he has worked with, including Rie Rasmussen, Jamie Peck and Charlotte Waters, have accused Richardson of inappropriate sexual behaviour and exploiting young female models.
Richardson has said the allegations are false and he considers himself "considerate and respectful" of his photography subjects. Models including Noot Seear, Daisy Lowe and Charlotte Free have defended him. Marc Jacobs has said that Richardson is "not ill-spirited".
Richardson held his first gallery showing in 1998. The show, entitled "These Colors Don’t Run" and held at Alleged Gallery, coincided with the release of his first book entitled Hysteric Glamour. His work was later featured at another show entitled "Smile" at Alleged Gallery. Richardson had his first Paris show at Galarie Emmanuel Perrotin in 1999. Richardson's "Feared by Men Desired by Women" was shown at an exhibition at London's Shine Gallery the following year.
"Terryworld," an exhibition of Richardson's work of the name, was shown in 2004 at Deitch Gallery in New York City. The Orange County Museum of Art showed Richardson's work as part of a group show entitled "Beautiful Losers" in 2005. "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. The same year, photographs from Richardson's book Hong Kong were shown at Art Hong Kong. Richardson's work was later shown at Los Angeles's OHWOW Gallery. The exhibition was titled "TERRYWOOD" and ran from February 24 to March 31, 2012.
Richardson has directed music videos since the late 1990s. He directed videos for Death in Vegas and Primal Scream as well as alternate music video of the song "Find a New Way" by the band Young Love and Whirlwind Heat's "Purple" featuring models Susan Eldridge and Kemp Muhl. He directed the music video for "Red Lips" by Sky Ferreira. He also makes a cameo appearance in Thirty Seconds to Mars's video for "Hurricane". On August 29, 2013 he directed Beyoncé in a music video at Coney Island for her single "XO". He also directed "Wrecking Ball" by Miley Cyrus. 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, the film has yet to be released. On August 21, 2017, Terry Richardson directed a new Anitta's 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. His work also explores ideas of sexuality, with many of the pieces featured in his books Kibosh and Terryworld depicting full-frontal nudity and both simulated and actual sexual acts. Initially, many of Richardson's subjects would be shot before a white background but he eventually expanded to other backdrops. He is also known for posing with his subjects, often giving them his trademark glasses so they may "pretend to be him" or, in the case of actress Chloë Sevigny, posing them in makeup and costume so that they look like him. Richardson counts Larry Clark, Nan Goldin, Diane Arbus and Robert Frank as early influences on his artistic style. His work has been praised by Helmut Newton.
Richardson is also known for his nonsexual portraiture. He has taken portraits of a wide variety of celebrities and politicians, including Sharon Stone, Gwyneth Paltrow, Lil' Kim, Cameron Diaz, Megan Fox, Lindsay Lohan, Kat Dennings, Liza Minnelli, Katy Perry, Kate Moss, Miley Cyrus, Miranda Kerr, Kim Kardashian, Samuel L. Jackson, Azealia Banks, Tracy Morgan, Jared Leto, Amy Winehouse, Jon Bon Jovi, A$AP Rocky, Pharrell Williams, Marilyn Manson, Lil Wayne, Daft Punk, Lana Del Rey, Shaun White, LeBron James, and Barack Obama.(1998) Hysteric Glamour. Hysteric Glamour (Tokyo). OCLC 86068704.(1999) Son of Bob. Little More (Tokyo). ISBN 978-4-947648-87-7.(2000) Terry Richardson – Feared by Men, Desired by Women. Shine Gallery (London). ISBN 978-0-9538451-1-8.(2002) Too Much. Sisley (Italy).(2004) Terry – The Terry Richardson Purple Book. Purple Institute (Paris). OCLC 62146661.(2004) Terry Richardson. Stern Gruner + Jahr (Hamburg). ISBN 978-3-570-19443-0.(2004) Terryworld. By Dian Hanson. Tashen (Hong Kong; Los Angeles). ISBN 978-3-8365-0191-0.(2006) Kibosh. Damiani Editore (Bologna). ISBN 978-88-89431-30-6.(2006) Manimal. Hysteric Glamour (Tokyo).(2007) Rio, Cidade Maravilhosa. Diesel/Vintage Denin (Brazil).(2011) Hong Kong. Diesel (Hong Kong).(2011) Mom & Dad. Mörel Books (London).(2011) Lady Gaga x Terry Richardson. Grand Central Publishing (New York). ISBN 978-1-4555-1389-5.
In 2010, Richardson became involved with RxArt, a charity that donates art to children's hospitals. In 2014, Richardson participated in a charity egg hunt sponsored by the House of Fabergé in New York City. The hunt benefited Studio in a School, a classroom arts program, and Elephant Family, a wildlife conservation program.
Richardson was married to model Nikki Uberti from 1996 to 1999.
On March 19, 2016, Richardson's partner Alexandra Bolotow gave birth to twin boys, named Rex and Roman. Richardson posted on Instagram that it was the most intense, inspiring, exhilarating, and humbling experience of his life.