In the early 1990s, troubling portraits began to appear more often and even emerge. Here is a gallery of troubling portraits (sources: Google News Archive, Google Scholar, Google Books)

Before 1985 (3 known cases, all listed below)

  • 1965: Nuclear confusion. “Although [An Inquiry into Enoughness, by Daniel Lang] produces no solutions, his ‘inquiry into’ provides a vivid and troubling portrait of the nuclear confusion we live in.”
  • 1979: The Supreme Court and the U.S. “He has drawn on his legal and personal experience to present a rich and troubling portrait of the court and the country.”
  • 1984: The Kid’s father. “And in addition to being musical and sexy and light-hearted, ‘Purple Rain’ also is dark and depressing, presenting a troubling portrait of the Kid’s father, who beats his wife and has thereby traumatized his son into seeking refuge in his own music and private lair.”

1986-1994 (approx. 70 cases, examples listed below)

  • 1986: Rural American rot. “[Sean Penn] again proves himself the best actor of his generation in ‘At Close Range,’ a powerful, uneven, troubling portrait of rural American rot.”
  • 1987: Sexism and racism. “The play [Darrah Cloud’s The Stick Wife] is termed ‘an expressionistic comedy’ and is an imaginative yet troubling portrait of sexism and racism.”
  • 1987: Ronald Reagan. “As the Iran-contra hearings fade off into the sunset, they leave behind a troubling portrait of a president who was strangely victimized both by his best and worst impulses.”
  • 1989: St. Paul (Minnesota). “Demographics and statistics paint a troubling portrait of St. Paul as it enters the next decade:”
  • 1989: Man’s alienation from nature. “Yet a consistent theme of ecological obsession pervades [The Pixies’ Doolittle]; the result is a troubling portrait of man’s alienation from nature”
  • 1990: America’s Children. “A federal commission Thursday painted a troubling portrait of America’s children, saying that too many are reaching adulthood ‘unhealthy, illiterate, unemployable and lacking both moral direction and a vision of a secure future.’”
  • 1991: The Albanian People. “Mr. Kadare thus accommodates his former Government’s nationalist ideology, yet at the same time draws a nuanced, troubling portrait of the Albanian people.”
  • 1992: Courtney Love. “A profile of Love in the September issue of Vanity Fair offers a troubling portrait of the lead singer for Los Angeles band Hole and her rock-star husband, who grew up in Aberdeen.”
  • 1992: Ross Perot. “[…] a troubling portrait emerges of the independent presidential candidate.”
  • 1993: Elizabeth Holtzman. “In a report released yesterday after a reluctant Ms. Holtzman gave her assent, the department paints a troubling portrait of a public official so driven and distracted by ambition that, at best, she put politics ahead of her office’s responsibilities.”
  • 1994: The Holocaust. “Director Marcel Ophuls’ 1988 Oscar winner is a troubling portrait of unimaginable evil.”
  • 1994: Portland (Maine). “Portland confronts a troubling portrait of itself in this week’s US News and World Report.”

1995-2004 (over 100 cases, examples listed below)

  • 1997: Timothy Leary. “The book’s final pages, a gathering of testimony by the many friends who surrounded Leary in his last days, offer a troubling portrait of a complex, driven man, always on stage, outwardly upbeat but secretly torn by anger, bitterness and a pervasive sense of loneliness.”
  • 1998: New Line Cinema. “It paints a troubling portrait of a 31-year-old pioneering film company that carved out a niche with films like A Nightmare On Elm Street.”
  • 1998: Jack Kerouac. “Recounted without the context given in earlier biographies and the larger humanity of Kerouac’s work, the story is left as gossip, to sully further an already troubling portrait.”
  • 1999: Saddleback College. “The accrediting panel painted a far more troubling portrait of Saddleback College.”
  • 2000: Contemporary America. “Black and White is volatile and messy, but it’s also uncommonly rich in ideas, and it leaves you with a deeply troubling portrait of contemporary America”
  • 2001: Jesus Christ. “The most radical and, for orthodox Christians, troubling portrait is the one drawn by the Jesus Seminar, a Santa Rosa, Calif.-based group of about 50 non-denominational scholars who investigate scriptural accounts of what Jesus said and did during his life.”
  • 2001: Edgardo Alfonzo. “Mets manager Bobby Valentine offered a slightly more troubling portrait of Alfonzo, who has battled various minor back ailments throughout his career.”
  • 2001: Domesticity. “Whereas Seurat’s ‘Sunday’ shows a whole panoply of Parisian society enjoying itself in public, Signac’s ‘Sunday’ is a more intimate and ultimately more troubling portrait of domesticity.”
  • 2001: Jarius Phillips and Marquita McCord (persons accused in a Virginia rape case). “Through it all, a troubling portrait arose of Phillips, McCord and the crimes with which they had been charged.”
  • 2002: Paul Shanley. “Despite the release of hundreds of pages of documents that paint a troubling portrait of the Rev. Paul R. Shanley and his relationship with the Boston Diocese, the Ford Family wants more.”
  • 2004: Hester Prynne. “She paints a vivid, troubling portrait of a woman who has fallen through the cracks.”
  • 2004: Social inattentiveness to an underclass. “Without labouring the point, this skilfully assembled film [José Padilha’s Bus 174] makes the authorities’ bungling of the situation on the bus seem symptomatic of wider institutional failures; what emerges is a troubling portrait of social inattentiveness to an underclass that looks so much more desperate with its City of God ghetto glamour stripped away.”

2005-date (over 100 cases, examples listed below)

  • 2005: The professional baseball locker room. “The ensuing congressional investigation turned up a troubling portrait of a locker room in which such substances were passed and injected by some players.”
  • 2006: Bush’s handling of the Iraq occupation. “While the book is studded with familiar administration sound bites about the importance of deposing Mr. Hussein, it paints a troubling portrait of the administration’s handling of the occupation.”
  • 2006: Student life at the U.S. Naval Academy. “But though much has improved since women first arrived — and many female graduates express great loyalty to the storied 161-year-old institution — a complex and sometimes troubling portrait of student life emerges from three recent studies sponsored by the Defense Department.”
  • 2007: Robert Hawkins. “A troubling portrait emerged Thursday of the disturbed teen who turned a cheerful shopping center into a killing field in a bid to gain fame as he ended his life.”
  • 2007: Seung-Hui Cho. “Investigators revealed details Tuesday about Cho that painted a troubling portrait of young man waiting to explode.”
  • 2008: A fictional Jewish Neo-Nazi. “Written and directed by Henry Bean, ‘Noise,’ which Mr. Bean has called partly autobiographical, is the second part of a projected ‘fanatic trilogy’ that began with ‘The Believer,’ a deep, troubling portrait of a Jewish neo-Nazi.”
  • 2009: Nidal Malik Hasan. “Emerging portrait troubling: Suspect’s name linked to radical postings on Web”
  • 2010: The FBI’s investigation of the Oklahoma City bombing: “When it is examined, a troubling portrait emerges of an agency eager to tailor its investigation for the purposes of prosecuting a criminal case, rather than doggedly seeking out the truth.”
  • 2010: Joseph Stack. “Troubling Portrait Emerges of Pilot Who Crashed Into Texas Building”

Recently, some portraits have been emerging but not identified as troubling, though they might be. The significance of these reports is unknown.

  • 2009: Richard Poplawski. “The emerging portrait of Richard Poplawski: a white-supremacist radical”
  • 2010: Dr. Amy Bishop. “The emerging portrait of neurobiologist and murder suspect Amy Bishop shows a disconnect between how she saw herself and her life and the actual reality of her experience.”

The earliest troubling portrait (1916) was hypothetical. A fictional character in The Girl Philippa suggested the possibility that one could be painted. He said, “I see. A man could paint a troubling portrait of her — a sermon on canvas.”