Selections mine, summary by Wikipedia, except where noted. Ordered by date.

Helter Skelter: The True Story of the Manson Murders – 1974
Helter Skelter: The True Story of The Manson Murders is a 1974 book by Vincent Bugliosi and Curt Gentry. Bugliosi had served as the prosecutor in the 1970 trial of Charles Manson. The book presents his firsthand account of the cases of Manson, Susan Atkins, Patricia Krenwinkel, and other members of the self-described Manson Family. It is the best-selling true crime book in history.

One L – 1977
One L tells author Scott Turow’s experience as a first-year Harvard Law School student. The book takes place in Cambridge, Massachusetts where Harvard University is located. First years, or One-L’s as they are often called, all face similar issues in their initial year of law school. Harvard, known for its reputation as one of the best law schools in the country, takes only about 12% of applicants.

Homicide: A Year on the Killing Streets – 1991
Homicide: A Year on the Killing Streets is a 1991 non-fiction book written by Baltimore Sun reporter David Simon describing a year spent with detectives from the Baltimore Police Department Homicide Unit. The book received the 1992 Edgar Award in the Best Fact Crime category.

Newjack: Guarding Sing Sing – 2000
Newjack: Guarding Sing Sing is a nonfiction book by journalist and professor Ted Conover published in 2000 by Vintage Books. In the book, Conover recounts his experience of learning firsthand about the New York State prison system by becoming a correctional officer for nearly a year. Conover sought the job of correctional officer after the New York State Department of Correctional Services denied his request to shadow the department’s employees in a journalist role.

The Last Face You’ll Ever See: The Private Life of the American Death Penalty – 2001
(Amazon summary)
In fascinating detail, Ivan Solotaroff introduces us to men who carry out executions. Although the emphasis is on the personal lives of these men and of those they have to put to death, The Last Face You’ll Ever See also addresses some of the deeper issues of the death penalty and connects the veiled, elusive figure of the executioner to the vast majority of Americans who have claimed to support executions since 1977. Why do we do it? Or, more exactly, why do we want to?

The Last Face You’ll Ever See is not about the polarizing issues of the death penalty — it is a firsthand report about the culture of executions: the executioners, the death-row inmates, and everyone involved in the act. An engrossing, unsettling, and provocative book, this work will forever affect anyone who reads it.

The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron – 2003
The Smartest Guys in the Room: The Amazing Rise and Scandalous Fall of Enron is a book by Bethany McLean and Peter Elkind, first published in 2003 by Portfolio Trade. In 2005, it was adapted into a documentary film, Enron: The Smartest Guys in the Room.

McLean and Elkind worked on the book when they both were Fortune senior writers. McLean had written a March 5, 2001 article for Fortune called, “Is Enron overpriced?”

The book is not only about the Enron scandal, but also describes the authors’ effort in following the developing story as it happened. It is based on hundreds of interviews and details from personal calendars, performance reviews, e-mails, and other documents. BusinessWeek called it, “The best book about the Enron debacle to date.”

Random Family: Love, Drugs, Trouble, and Coming of Age in the Bronx – 2003
Random Family: Love, Drugs, Trouble, and Coming of Age in the Bronx is a 2003 narrative non-fiction study of urban life by American writer Adrian Nicole LeBlanc.
The book, LeBlanc’s first, took more than 10 years to research and write. Random Family is a nonfiction account of the struggles of two women and their family as they deal with love, drug dealers, babies and prison time in the Bronx. LeBlanc began the long period of research after reporting on a piece in Newsday about the trial of “a hugely successful heroin dealer” named George ‘Boy George’ Rivera.

Blue Blood – 2004
… Blue Blood (2004), which covers Conlon’s years in the NYPD, his work conducting street-level narcotics enforcement in the Housing Bureau, his family’s law enforcement background, and various anecdotes about the history of policing. The book received a favorable review on the cover of The New York Times Book Review, debuted at #9 on the Times Best Seller list, and remained on the list for two weeks.[citation needed]

Just Mercy: A Story of Justice and Redemption – 2014
Just Mercy: A Story of Justice and Redemption (2014) is a memoir by American attorney Bryan Stevenson that documents his career defending disadvantaged clients. The book, focusing on injustices in the United States judicial system, alternates chapters between documenting Stevenson’s efforts to overturn the wrongful conviction of Walter McMillian and his work on other cases, including children who receive life sentences, and other poor or marginalized clients.

The Second Chance Club: Hardship and Hope After Prison – 2020
(Amazon summary)
A former parole officer shines a bright light on a huge yet hidden part of our justice system through the intertwining stories of seven parolees striving to survive the chaos that awaits them after prison in this illuminating and dramatic book.

Prompted by a dead-end retail job and a vague desire to increase the amount of justice in his hometown, Jason Hardy became a parole officer in New Orleans at the worst possible moment. Louisiana’s incarceration rates were the highest in the US and his department’s caseload had just been increased to 220 “offenders” per parole officer, whereas the national average is around 100. Almost immediately, he discovered that the biggest problem with our prison system is what we do—and don’t do—when people get out of prison.