The first thing David Milch, 74, wrote for television was a 1982 episode of Hill Street Blues. Before that, he'd primarily been an academic. He graduated summa cum laude from Yale, taught seminars on fiction and poetry, earned an MFA from the Iowa Writers Workshop and worked on a two-volume textbook anthology of American literature. This would all fit nicely on an up-and-coming English lit professor's résumé, except he also got kicked out of Yale Law School for being arrested after, according to The New York Times, "he destroyed a police car's roof lights with a shotgun blast." (Some form of psychedelic, probably LSD, was involved.)

Getting the Hill Street Blues script assignment was his exit visa from academia. "I knew that you don't get a lot of chances," Milch told the Los Angeles Times in 1998. "The first script I turned in had a lot of problems because I had never seen a script, but I listened pretty hard." That third-season episode, "Trial by Fury," went on to win an Emmy, a WGA award and a Humanitas prize that paid him $15,000. (Milch used the money to buy a racehorse.) "David's a star," said late Hill Street co-creator Steven Bochco in 1994. "Whatever it is that makes certain individuals utterly compelling, David has." Milch and Bochco went on to create ABC's legendary NYPD Blue (for which he won two more writing Emmys) and a flop, Brooklyn South, for CBS. But in 2004, Milch was back on top with HBO's acclaimed Deadwood. Then, even for a guy who weathered some notable ups and downs, Milch had a major rise and fall with Luck.

The 2011 HBO series starring Dustin Hoffman took off as a critical success, but three horses died during production, and the show was canceled in the second season. Then Milch's gambling excesses caught up with him. In 2016, The Hollywood Reporter estimated Milch had earned more than $100 million from TV writing and owed the IRS $17 million. He announced in April that he has Alzheimer's. The long-awaited Deadwood movie premiered May 31 on HBO.

This story first appeared in a June stand-alone issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.