Madeleine Sackler started off her career editing films. She directed and produced her first film, The Lottery, in 2010 and was shortlisted for an academy award. Two years later she directed and produced Duke 91 & 92: Back to Back, a documentary about the Duke Blue Devils' repeat basketball national championship seasons. Dangerous Acts Starring the Unstable Elements of Belarus (2013) debuted at the Toronto International Film Festival in 2013 and is comprised of smuggled footage from the oppressive Belarussian regime. Dangerous Acts won an Emmy Award and received the Grand Jury prize at One World International Human Rights Documentary Film Festival, the Golden Butterfly at The Hague Movies that Matter Festival, Best Documentary at the Minneapolis St. Paul International Film Festival, the Audience Award at Lighthouse International Film Festival, and 3 awards at Biografilm Festival, including the Audience Award.
With her film company, Great Curve Films, Madeleine Sackler went on to direct and produce two films which she filmed entirely within a maximum-security prison: the documentary, It's a Hard Truth Ain't It, and the critically acclaimed feature film O.G., starring Jeffrey Wright and Theothus Carter. She received the Bill Webber Award for Community Service from Hudson Link for Higher Education in Prison for the two films.