When LaChapelle was 17 years old, he met Andy Warhol, who hired him as a photographer for Interview. Warhol reportedly told LaChapelle "Do whatever you want. Just make sure everybody looks good." LaChapelle's friends during this period included Keith Haring and Jean-Michel Basquiat. LaChapelle's images subsequently appeared on the covers and pages of magazines such as Details, GQ, i-D, The New York Times Magazine, Rolling Stone, The Face, Vanity Fair, Vogue Italia, and Vogue Paris.LaChapelle's work has been called "meticulously created in a high-gloss, color-popping, hyper-realistic style", and his photos are known to, "crackle with subversive – or at least hilarious – ideas, rude energy and laughter. They are full of juicy life." In 1995 David LaChapelle shot the famous 'kissing sailors' advertisement for Diesel. It was staged at the peace celebration of World War II and became one of the first public advertisements showing a gay or lesbian couple kissing. Much of its controversy was due it being published at height of the Don't ask, Don't tell debates in United States, which had led to the U.S. Government to bar openly gay, lesbian, or bisexual persons from military service. In a long article published by Frieze in 1996, the advertisement was credited for its "overarching tone of heavy-handed humor and sarcasm". In September 2011 when the Don't ask, Don't tell law was finally removed by President Barack Obama, Renzo Rosso, the founder and president of Diesel who originally had approved and pushed for the advertisement, said "16 years ago people wouldn't stop complaining about this ad. Now it's (open bi- and homosexuality in the U.S. Military) finally accepted legally.
The photograph "Deluge" at the "Thus Spoke LaChapelle" ("Tak Pravil LaChapelle") exhibition, Galerie Rudolfinum, Prague, 2011 Themes in LaChapelle's art photography, which he has developed in his Maui home, include salvation, redemption, paradise, and consumerism. It is clear that LaChapelle's moving in this, "new direction highlights his interest and understanding of both contemporary practice and art history". LaChapelle's images "both bizarre and gorgeous have forged a singular style that is unique, original, and perfectly unmistakeable. He has photographed personalities such as Tupac Shakur, Aaliyah, Madonna, Amanda Lepore, Eminem, Philip Johnson, Lance Armstrong, Pamela Anderson, Katy Perry, Lady Gaga, Whitney Houston, Jay Z, Nicki Minaj, Kanye West, Mariah Carey, Naomi Campbell, Uma Thurman, Elizabeth Taylor, David Beckham, Jeff Koons, Leonardo DiCaprio, Hillary Clinton, Muhummad Ali, Björk and Angelina Jolie. His photographs have been collected in a number of books. LaChapelle Land (1996) was selected as one of 101 "Seminal Photographic Books of the Twentieth Century" and is "highly valued by collectors".His second book, Hotel LaChapelle (1999), was described as a "garish, sexy, enchanting trip".[ Heaven to Hell (2006) featured "almost twice as many images as its predecessors", and "is an explosive compilation of new work by the visionary photographer." LaChapelle, Artists and Prostitutes (2006), a limited-edition, signed, numbered book 19.7 inches (50 cm) high and 13.6 inches (35 cm) wide, contains 688 pages of photographs taken between 1985 and 2005. Artists and Prostitutes was published by Taschen and includes a photograph of the publisher Benedikt Taschen in a sadomasochism scene. In the last decade LaChapelle has returned to a focus on fine art photography and has exhibited his work in several galleries and museums. LaChapelle has had solo museum exhibitions at the Barbican Museum in London (2002), Kausthaus Wien in Vienna (2002), Palazzo Reale in Milan
LaChapelle cites a number of artists who have influenced his photography. In a 2009 interview, he mentioned the Baroque painters Andrea Pozzo and Caravaggio as two of his favorites. Critics have noted that LaChapelle's work has been influenced by Salvador Dalí, Jeff Koons, Michelangelo, Cindy Sherman, and Andy Warhol. In a New York Times article by Amy M. Spindler, photographer Richard Avedon states "of all the photographers inventing surreal images. It was Mr. LaChapelle who has the potential to be the genre's Magritte. Helmut Newton has also contributed to the discourse on LaChapelle, stating in a NYT article by Cathy Horyn "He [LaChapelle] isn't very impressed by current photography. 'There's a lot of pornographic pictures taken by the young today...A lot of the nudity is gratuitous. But someone who makes me laugh is David LaChapelle. I think he is very bright, very funny, and good'"