Wolf worked as an advertising copywriter at Benton & Bowles creating commercials for Crest toothpaste, all the while writing screenplays in the hopes of a film career. It was at this time that he briefly collaborated on a screenplay with Oliver Stone, who was a struggling screenwriter at the time. He moved to Los Angeles, California after a few years and had three screenplays produced; one of these films, Masquerade starring Rob Lowe and Meg Tilly, was well received. He started his television career as a staff writer on Hill Street Blues and was nominated for his first Emmy for an episode (entitled "What Are Friends For?") on which he was the only writer. He moved from there to Miami Vice, where he was a supervising producer.
Wolf developed Chicago Fire, a drama about a group of men and women working at the Chicago Fire Department. The series was picked up by NBC in May 2012, and premiered on October 10, 2012, with meek numbers in the ratings and minimal reviews in the first few weeks before spiking to NBC's #2 scripted drama series, under Revolution. In March 2013, NBC announced intentions for a spin-off of Chicago Fire, revolving around the Chicago Police Department.Derek Haas, Michael W. Brandt, and Matt Olmstead are executive producers under Wolf. Afterwards, Wolf developed the unscripted show Cold Justice, a documentary drama, for TNT.
In addition to having been a classmate of former U.S. President George W. Bush, Wolf was an employer of Fred Thompson, who sought the Republican nomination for President in 2008 with help of the national attention he gained playing the district attorney on Law & Order. Wolf supported Thompson in his bid, as he did Bush. It was reported that Wolf contributed to Thompson's campaign before he officially announced he was running.
Wolf's future projects for NBC are an American adaption of the United Kingdom psychological legal drama series Injustice as well as a drama series revolving around a satanic cult, tenatively titled The Church. Wolf is writing the latter project with Howard Franklin. Wolf also has an untitled pilot about an insurance investigator on USA Network.
With Wolf pursuing projects other than Law & Order, he and current Law & Order: Special Victims Unit show runner/executive producer Warren Leight sometimes discuss the future of the Law & Order franchise and revitalizing it; Leight commenting "(Dick Wolf and I) sometimes talk in general terms of where (the franchise) could go. I'm curious to see if there's another iteration somewhere down the line."