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Movies like Chicago at the Crossroad (2019)

The best movies like Chicago at the Crossroad (2019) are The Perfect Neighbor (2025), O.J.: Made in America (2016) and Whitey: United States of America v. James J. Bulger (2014). If Chicago at the Crossroad hooked you with its crime and documentary, these 30 similar films are what to watch next, and every pick says why it matches.

Quick picks

  1. The Perfect Neighbor (2025)

    Police bodycam footage reveals how a long-running neighborhood dispute turned fatal in this documentary about fear, prejudice and Stand Your Ground laws.

    Why it matches: Recommended by TMDB viewers · both crime & documentary

    Popcorn FlickMovies like this
  2. O.J.: Made in America (2016)

    A chronicle of the rise and fall of O.J. Simpson, whose high-profile murder trial exposed the extent of American racial tensions, revealing a fractured and divided nation.

    Why it matches: Recommended by TMDB viewers · both documentary & crime

    Absolute CinemaMovies like this
  3. Whitey: United States of America v. James J. Bulger (2014)

    A documentary that captures the sensational trial of infamous gangster James 'Whitey' Bulger, using the legal proceedings as a springboard to explore allegations of corruption within the highest levels of law enforcement. Academy Award-nominated filmmaker Joe Berlinger examines Bulger's relationship with the FBI and Department of Justice that allowed him to reign over a criminal empire in Boston for decades.

    Why it matches: Recommended by TMDB viewers · both crime & documentary

    Popcorn FlickMovies like this
  4. The Killing of America (1981)

    A documentary of the decline of America, composed of archival material and exclusive footage, carnage, madness, and mayhem with an unapologetic sincerity on the factual depiction of violence in the industrialized nation of the United States. Featuring a juxtaposition of detailed accounts of terrible acts, brutal behavior, and interviews from experts and convicted killers alike.

    Why it matches: Recommended by TMDB viewers · both documentary & crime

    Worth the HypeMovies like this
  5. The Mystery of D.B. Cooper (2020)

    This documentary brings to life the stories of four people believed by their family and friends to be “DB Cooper,” a man who hijacked a 727 flying out of Seattle and jumped from the plane over the wilds of Washington State with a parachute and $200,000, never to be heard from again.

    Why it matches: Recommended by TMDB viewers · both documentary & crime

    Popcorn FlickMovies like this
  6. Ted Bundy: Mind of a Monster (2019)

    New exclusive access and never before heard testimony gives a unique insight into the mind of America's most notorious serial killer, Ted Bundy. Breathtaking archive from the time and the voice of Bundy himself, reveals the monster inside the man.

    Why it matches: Recommended by TMDB viewers · both crime & documentary

    Worth the HypeMovies like this
  7. Tales of the Grim Sleeper (2014)

    When Lonnie Franklin Jr. was arrested in South Central Los Angeles in 2010 as the suspected murderer of a string of young black women, police hailed it as the culmination of 20 years of investigations. Four years later documentary filmmaker Nick Broomfield took his camera to the alleged killer’s neighborhood for another view.

    Why it matches: Recommended by TMDB viewers · both crime & documentary

    Popcorn FlickMovies like this
  8. Deliver Us from Evil (2006)

    Documentary filmmaker Amy Berg investigates the life of 30-year pedophile Father Oliver O'Grady and exposes the corruption inside the Catholic Church that allowed him to abuse countless children. Victims' stories and a disturbing interview with O'Grady offer a view into the troubled mind of the spiritual leader who moved from parish to parish gaining trust ... all the while betraying so many.

    Why it matches: Recommended by TMDB viewers · both crime & documentary

    Worth the HypeMovies like this
  9. Long Shot (2017)

    When Juan Catalan is arrested for a murder he insists he didn't commit, he builds his case for innocence around unexpected raw footage.

    Why it matches: Recommended by TMDB viewers · both crime & documentary

    Worth the HypeMovies like this
  10. Maternal Instinct (2026)

    Police pull over a woman who claims she just gave birth. But the baby — and the blood — aren't hers. Twisted lies unravel in this true-crime documentary.

    Why it matches: Recommended by TMDB viewers · both documentary & crime

    Worth the HypeMovies like this
  11. Oklahoma City Bombing: American Terror (2025)

    This gripping documentary revisits the shocking 1995 bombing of an Oklahoma City federal building, the deadliest act of domestic terrorism in US history.

    Why it matches: Recommended by TMDB viewers · both documentary & crime

    Popcorn FlickMovies like this
  12. Out of Thin Air (2017)

    Set within the stark Icelandic landscape, OUT OF THIN AIR examines the 1976 police investigation into the disappearance of two men in the early 1970s.

    Why it matches: Recommended by TMDB viewers · both documentary & crime

  13. H.H. Holmes: America's First Serial Killer (2004)

    Torture chambers, acid vats, greased chutes and gassing rooms were just some of the devices of death designed by the Torture Doctor, H.H. Holmes in his castle of horrors. Follows Holmes' entire life as a criminal mastermind.

    Why it matches: Recommended by TMDB viewers · both crime & documentary

    Popcorn FlickMovies like this
  14. The Crash (2026)

    A teen slams her car into a building, killing her boyfriend and his friend. What seems like a tragic accident becomes a murder case.

    Why it matches: Recommended by TMDB viewers · both documentary & crime

    Popcorn FlickMovies like this
  15. Hoop Dreams (1994)

    Every school day, African-American teenagers William Gates and Arthur Agee travel 90 minutes each way from inner-city Chicago to St. Joseph High School in Westchester, Illinois, a predominately white suburban school well-known for the excellence of its basketball program. Gates and Agee dream of NBA stardom, and with the support of their close-knit families, they battle the social and physical obstacles that stand in their way. This acclaimed documentary was shot over the course of five years.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  16. All the Empty Rooms (2025)

    A journalist and a photographer set out to memorialize the bedrooms left behind by children killed in school shootings.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  17. Crips and Bloods: Made in America (2009)

    With a first-person look at the notorious Crips and Bloods, this film examines the conditions that have lead to decades of devastating gang violence among young African Americans growing up in South Los Angeles.

    Why it matches: Recommended by TMDB viewers · both documentary

    Popcorn FlickMovies like this
  18. A Toxic Love Story (2026)

    A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.

    Why it matches: Recommended by TMDB viewers · both documentary

    Popcorn FlickMovies like this
  19. 13th (2016)

    An in-depth look at the prison system in the United States and how it reveals the nation's history of racial inequality.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  20. Come See Me in the Good Light (2025)

    In an intimate and joyful story of love in the face of loss, celebrated poets Andrea Gibson and Megan Falley find strength—and unexpected hilarity—in what might be their final year together.

    Why it matches: Recommended by TMDB viewers · both documentary

    Worth the HypeMovies like this
  21. The Perfect Victim (2012)

    For over thirty years, three women have languished in Missouri State prison under unjust sentences for killing their abusive husbands. Denied the opportunity to enter the abuse into evidence, each of the women represents a system broken by outdated and media-sensationalized stereotypes. When a greater understanding of the "battered" syndrome change legal practices in 2000, Missouri's Governor crafts a new law demanding the parole board reevaluate each woman's case.

    Why it matches: Similar story and style · both crime & documentary

  22. Radical Disciple: The Story of Father Pfleger (2009)

    The story of Catholic iconoclast Michael Pfleger who made it his mission to transform the drug ravaged south side Chicago community surrounding his parish. In so doing, Father Mike has run directly into conflict with the local Catholic hierarchy. The film explores issues of racism, the power of the media, and the tension between Pfleger's 'gospel of the streets' versus traditional Church theology.

    Why it matches: Similar story and style · both documentary

  23. Judgment Night (1993)

    Four young friends, while taking a shortcut en route to a local boxing match, witness a brutal murder which leaves them running for their lives.

    Why it matches: Similar story and style · both crime

    Popcorn FlickMovies like this
  24. The Long Night (2025)

    When her brother disappears, Anna enlists a violent man from her past to extract the truth and drags her partner into a night of brutality that may cost them more than just their conscience.

    Why it matches: Similar story and style · both crime

  25. U.S. Marshals (1998)

    U.S. Marshal Sam Gerard is accompanying a plane load of convicts from Chicago to New York. The plane crashes spectacularly, and Mark Sheridan escapes. But when Diplomatic Security Agent John Royce is assigned to help Gerard recapture Sheridan, it becomes clear that Sheridan is more than just another murderer.

    Why it matches: Similar story and style · both crime

    Popcorn FlickMovies like this
  26. Murder by Numbers (2002)

    Tenacious homicide detective Cassie Mayweather and her still-green partner are working a murder case, attempting to profile two malevolently brilliant young men: cold, calculating killers whose dark secrets might explain their crimes.

    Why it matches: Similar story and style · both crime

    Popcorn FlickMovies like this
  27. True Romance (1993)

    Clarence marries hooker Alabama, steals cocaine from her pimp, and tries to sell it in Hollywood, while the owners of the coke try to reclaim it.

    Why it matches: Similar story and style · both crime

    Worth the HypeMovies like this
  28. Insomnia (2002)

    Two Los Angeles homicide detectives are dispatched to a northern town where the sun doesn't set to investigate the methodical murder of a local teen.

    Why it matches: Similar story and style · both crime

    Worth the HypeMovies like this
  29. Twitz from Pluto: Graff, Jackass and TV Casualty (2022)

    The story of two teenage extraterrestrial refugees from the planet Pluto, who escape to Earth after their planet is destroyed by the US government, as it was deemed “insignificant.” For many years prior, tensions between the Plutonians and the Earthlings had seen a steady incline, as Pluto held camps where Earthlings were experimented on and tortured. The two aliens make their crash landing, undertake human form and undergo the aliases “Hugh Jainus” and “E. Rection”. In an effort to wage revenge on the nation, with their brainwashed sidekick Potator under their wing, the trio hijack television stations worldwide and broadcast mind-numbingly stupid and ridiculous, yet insane and often violent programs to dumb down and distract the nation’s citizens from their devious plans. The tube tells the story...

    Why it matches: Similar story and style · both crime

  30. Revolver Rani (2014)

    Alka Singh, the leader of a political party, and her obsessive love for Rohan Mehra, a rising star of Bollywood.

    Why it matches: Similar story and style · both crime

Like Chicago at the Crossroad and something else?

Blend two favourites and we’ll find the films in between.

Frequently asked questions

What are the best movies like Chicago at the Crossroad?

The closest matches to Chicago at the Crossroad are The Perfect Neighbor (2025), O.J.: Made in America (2016) and Whitey: United States of America v. James J. Bulger (2014). Below are 27 more, each with the reason it matches.

What should I watch after Chicago at the Crossroad?

Start with The Perfect Neighbor (2025), the closest match to Chicago at the Crossroad.

What is the highest-rated movie like Chicago at the Crossroad?

O.J.: Made in America (2016), rated 8.4/10 by 271 TMDB users.

What is the newest movie like Chicago at the Crossroad?

A Toxic Love Story (2026) is the most recent release on this list.

Are there English movies like Chicago at the Crossroad?

Yes: The Perfect Neighbor (2025), O.J.: Made in America (2016) and Whitey: United States of America v. James J. Bulger (2014).

How are movies similar to Chicago at the Crossroad chosen?

First come films that Trakt’s viewers watch alongside Chicago at the Crossroad, then TMDB’s recommendations and films it rates as similar in story and genre. Each pick says which signal put it there.

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