Richman's first big role was in the hit 1986 drama film River's Edge as Tony, he also starred in 2 other films that year, Thrashin' and Modern Girls. He appeared in the 1987 film The Allnighter and the 1988 sequel film, Fright Night Part 2. In 1989, he played a role in the cult film Heathers. His other films include Kiss Kiss Bang Bang (2005), The Education of Charlie Banks (2007) and a minor role in Oliver Stone's Natural Born Killers and Adam Collis Sunset Strip.
In 1991, Richman developed a professional relationship with Axl Rose from Guns N' Roses that led to him directing their video for a cover of Paul McCartney's "Live and Let Die". He is featured prominently in the Guns N' Roses home video titled, Making F@#$ing Videos Part 1 which chronicles his involvement in co-writing the promotional video for the GN'R hit "Don't Cry". Richman's involvement with the band landed him the inclusion of his photo in the booklet of their multi-platinum selling Use Your Illusion I and Use Your Illusion II albums. Richman had a small speaking role in the spoken word section of their cover of "Knockin' on Heaven's Door".
