Movies Like The Sexiest Man in Winnipeg

If you liked The Sexiest Man in Winnipeg (2025), a crime and documentary movie directed by Charlie Siskel and Ben Daughtrey, here are 20 movies with a similar feel, based on TMDB's recommendations. Each one links to its cast, trailer and where it's streaming.

1
Voyeur (2017)
★ 5.9/10Also documentary and crime
Legendary journalist Gay Talese unmasks a motel owner who spied on his guests for decades. But his bombshell story soon becomes a scandal of its own.
2
Ted Bundy: Mind of a Monster (2019)
★ 7.6/10Also crime and documentary
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…
3
Deliver Us from Evil (2006)
★ 7.2/10Also crime and documentary
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…
4
Tales of the Grim Sleeper (2014)
★ 6.3/10Also crime and documentary
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…
5
The Accountant of Auschwitz (2018)
★ 6.9/10Also documentary and crime
Oskar Gröning, known as the "Accountant of Auschwitz," was charged with the murder of 300,000 Jews. When he took the stand in 2015, at the age of 94, his trial made headlines worldwide.
6
Maternal Instinct (2026)
★ 7.2/10Also documentary and crime
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.
7
Out of Thin Air (2017)
★ 5.9/10Also documentary and crime
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.
8
Long Shot (2017)
★ 7.2/10Also crime and documentary
When Juan Catalan is arrested for a murder he insists he didn't commit, he builds his case for innocence around unexpected raw footage.
9
How to Rob a Bank (2024)
★ 6.7/10Also documentary and crime
In this true-crime documentary, a charismatic rebel in 1990s Seattle pulls off an unprecedented string of bank robberies straight out of the movies.
10
The Crash (2026)
★ 6.8/10Also documentary and crime
A teen slams her car into a building, killing her boyfriend and his friend. What seems like a tragic accident becomes a murder case.
11
Stolen: Heist of the Century (2025)
★ 7.2/10Also documentary and crime
Antwerp, 2003. A gang of thieves rob the impenetrable Diamond Center. Who was behind one of the world's biggest heists - and how did they pull it off?
12
A Toxic Love Story (2026)
★ 6.4/10Also documentary
A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.
13
The Mystery of D.B. Cooper (2020)
★ 6.3/10Also documentary and crime
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…
14
Mommy Dead and Dearest (2017)
★ 7.4/10Also crime and documentary
Child abuse, mental illness, and forbidden love converge in this mystery involving a mother and daughter who were thought to be living a fairy tale life that turned out to be a living nightmare.
15
Evil Influencer: The Jodi Hildebrandt Story (2025)
★ 6.2/10Also documentary
Unravel the case of Utah therapist Jodi Hildebrandt, whose child abuse arrest with parenting YouTuber Ruby Franke exposed a twisted tale of manipulation.
16
Bikram: Yogi, Guru, Predator (2019)
★ 6.3/10Also documentary and crime
The spectacular rise and scandalous fall of hot-yoga evangelist Bikram Choudhury is chronicled through archival footage and extensive insider interviews.
17
Whitey: United States of America v. James J. Bulger (2014)
★ 6.4/10Also crime and documentary
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…
18
Untold: Crime & Penalties (2021)
★ 7.1/10Also documentary and crime
They were the bad boys of hockey — a team bought by a man with mob ties, run by his 17-year-old son, and with a rep for being as violent as they were good.
19
O.J.: Made in America (2016)
★ 8.4/10Also documentary and crime
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.
20
Dream/Killer (2015)
★ 6.8/10Also documentary and crime
In 2005, 20-year-old Ryan Ferguson was convicted and sentenced to 40 years in prison for a crime he did not commit. dream/killer is the story of how his father Bill embarked on 10-year campaign to prove Ryan’s…