His work includes the documentary films The War Room, A Perfect Candidate, Thin, The September Issue, The World According to Dick Cheney and Listen to Me Marlon; the non-fiction television series Black.

White., American High, Martha , Freshman Diaries and 30 Days; the prime time drama series Nashville; the scripted podcast, The Oval Office Tapes; and the feature film If I Stay.

"[24] In 1994, Cutler and co-director/producer David Van Taylor spent eleven months following the U.S. Senate campaign of Lt. Col. Oliver North who was running as a Republican to take the seat occupied by Democrat Charles S.

[32] The following January, the Edgewise short Monte Hellman: American Auteur (directed by George Hickenlooper) was screened in competition at the Sundance Film Festival.

[33] In 1999, Cutler set out to create the first network "nonfiction drama," a form of documentary serial storytelling that was new to American commercial prime time television.

Over the course of the year, they collected more than 2800 hours of footage, 70 percent of which was shot by Cutler's crews, and the rest of which was filmed by the students themselves with digital cameras provided by the filmmakers.

As a follow-up to American High, Showtime commissioned Cutler to spend the 2002–2003 school year with a group of freshmen at the University of Texas in Austin.

[40] As with American High Cutler and his team assembled a group of students, filmed them cinema verite style for the full school year and provided them with digital cameras so that they could contribute their own footage to the project as well.

[40] When Freshman Diaries premiered on Showtime in August, 2003, Steve Johnson wrote in The Chicago Tribune, "Yes, the new 'reality' genre has dominated television, too often with simple-minded tributes to hormones and humiliation.

[41] David Zurawik of The Baltimore Sun wrote, "This is the place where the immediacy, and edge, of reality TV meets the power of the documentary film to show us the world as seen through the eyes of others".

[45] Also in 2005, Cutler was invited by executive producer Joe Berlinger to contribute a film to the History Channel's documentary series, Ten Days That Unexpectedly Changed America.

[49] While The September Issue features a host of Vogue personalities, designers, models, photographers, and others, its principal subject is the conflict-laden but deeply symbiotic relationship between the powerful, influential and notoriously frosty Wintour and her passionate fire-haired Creative Director Grace Coddington.

[48] The September Issue received its World Premiere at the 2009 Sundance Film Festival, where it screened in competition and won the Grand Jury Prize for Cinematography.

[33] Hick Town tells the story of then-Denver Mayor (later Colorado Governor) John Hickenlooper, who was the director's cousin, as the city of Denver was gearing up to host the 2008 Democratic National Convention.

[64] In October 2020, R. J. Cutler launched his production company This Machine Filmworks with the backing of Industrial Media (now Sony Pictures Television Nonfiction).

[68] Cutler made a deal to merge his production company's projects with Evolution Film and Tape, effectively shutting down Actual Reality Pictures.

[68] In 2010, HBO ordered a pilot of Spring/Fall, a show set in the fashion industry and executive produced by Cutler, Jimmy Miller, and writer Kate Robin.

[71] In 2011, ABC ordered a pilot for Nashville, executive produced by Cutler, Callie Khouri and Steve Buchanan, president of Gaylord Entertainment (owner of the Grand Ole Opry.

[79] In 2013, CBS signed Cutler to direct the pilot of The Ordained, executive produced by Frank Marshall and written by Lisa Takeuchi Cullen.

[80] The show about a Kennedy-like political family starred Charlie Cox, Sam Neill, Audra McDonald, Jorge Garcia and Hope Davis.

[83][84] In 2014, CBS announced that it had entered into a two-year first-look television deal with Cutler to develop, produce and direct scripted projects.

[87] He listed his Best Movies Ever for Newsweek as Oliver Stone’s Wall Street, Elia Kazan’s On the Waterfront, Woody Allen’s Crimes and Misdemeanors, Preston Sturges’ The Lady Eve, Bob Fosse’s All That Jazz, Terrence Malick’s Badlands, Barbara Kopple’s Harlan County, USA and Sidney Lumet’s Dog Day Afternoon.

[88] While making The September Issue Cutler was influenced by Robert Drew’s Crisis, the Maysles Brothers’ Gimme Shelter, George Cukor’s Philadelphia Story and Preston Sturges’ The Lady Eve.