Weber has directed several films, including Let's Get Lost (1988), a documentary about jazz musician Chet Baker, and Chop Suey (2001), a portrait of a wrestler.

Nan Bush, his longtime companion and agent, was able to secure a contract with Federated Department Stores to shoot the 1978 Bloomingdales mail catalog.

[13] His straightforward black-and-white shots, featuring an unclothed woman and man on a swing facing each other, two clothed men in bed, and model Marcus Schenkenberg suggestively holding jeans in front of himself in a shower, catapulted them both into the national spotlight.

[13][14] His photograph for Calvin Klein of Olympic athlete Tom Hintnaus in white briefs is an iconic image.

Some of Weber's earliest fashion photography appeared in the SoHo Weekly News and featured a spread of men wearing only underwear.

His editorial work has appeared in Vogue, GQ, Vanity Fair, Elle, Life, Interview, and Rolling Stones magazines.

While he originally intended to make a short to accompany an exhibition he was opening in Paris, Weber became very excited when he reviewed the dailies and decided to continue the story.Broken Noses (1987), the resulting feature documentary, was nominated for the Grand Jury Award at Sundance in 1988.

[3] But filming with Baker continued right through the presentation of Broken Noses in Cannes that year—with Weber ultimately assembling the footage of travel, recording sessions, and interviews into his second feature, Let's Get Lost (1988).

[3] Filming took a year with Weber approaching it, as he told The Times of London, "like his (Baker's) interpretation of a song, open-ended, not lyrical or strict.

One of his most engaging discoveries is the 91-year-old Sir Wilfred, who as a young desert explorer made photographs of Bedouin tribesman that prefigure Mr. Weber's own work.

(He) is a shameless old softie for whom dogs are emblematic of a happy home, (and)‘cherishes domestic security amid the fear created by the…attacks.

[3] In December 2017, model Jason Boyce sued Weber in New York State Supreme Court, claiming sexual assault, including inappropriate touching and kissing during a 2014 casting session.

[47] A second model, Mark Ricketson, came forward in December 2017 alleging similar claims and joined Boyce's lawsuit against Weber.

[5] In January 2019, it was reported that Weber asked to dismiss the original suit by Jason Boyce, with evidence provided that the model sent him racy photos and texts prior to and after the shoots.

In 1996 he directed the video for the Pet Shop Boys single "Se a vida é (That's the Way Life Is)" on location in a Wet 'n' Wild, a water park near Orlando, Florida.

His dedication to the All-American project is motivated by a desire to connect, inspire, and support the work of emerging artists.