Movies Like Cheat You Fair: The Story of Maxwell Street

If you liked Cheat You Fair: The Story of Maxwell Street (2006), a movie directed by Phil Ranstrom, 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
Cadillac Records (2008)
★ 7.1/10
The story of sex, violence, race and rock and roll in 1950s Chicago, and the exciting but turbulent lives of some of America's musical legends, including Muddy Waters, Leonard Chess, Little Walter, Howlin' Wolf, Etta…
2
The Trial of the Chicago 7 (2020)
★ 7.7/10
What was supposed to be a peaceful protest turned into a violent clash with the police. What followed was one of the most notorious trials in history.
3
Bessie (2015)
★ 6.4/10
The story of legendary blues performer, Bessie Smith, who rose to fame during the 1920s and '30s.
4
LCD Soundsystem: Shut Up and Play the Hits (2012)
★ 6.9/10
An intimate portrait of Brooklyn-based electronic rock band LCD Soundsystem's then-final live show on April 2, 2011, capturing both the exuberant, three-hour farewell concert at New York City's Madison Square Garden…
5
A Toxic Love Story (2026)
★ 6.4/10
A string of threatening emails escalates into a revenge plot involving a newly married US marshal and his ex-girlfriend.
6
The Curse of the Dragon (1993)
★ 7.2/10
A 1993 documentary film about Bruce Lee. The film includes interviews from some of his fellow students and opponents who worked alongside him in his movies.
7
Pennies from Heaven (1981)
★ 6.1/10
During the Great Depression, a sheet music salesman seeks to escape his dreary life through popular music and a love affair with an innocent schoolteacher.
8
Hounddog (2008)
★ 6.5/10
A drama set in the American South, where a precocious, troubled girl finds a safe haven in the music and movement of Elvis Presley.
9
Roger & Me (1989)
★ 7.1/10
A documentary about the closure of General Motors' plant at Flint, Michigan, which resulted in the loss of 30,000 jobs. Details the attempts of filmmaker Michael Moore to get an interview with GM CEO Roger Smith.
10
Western Stars (2019)
★ 7/10
The incomparable Bruce Springsteen performs his critically acclaimed latest album and muses on life, rock, and the American dream, in this intimate and personal concert film co-directed by Thom Zimny and Springsteen…
11
Eleanor the Great (2025)
★ 6.8/10
94-year-old Eleanor Morgenstein tries to rebuild her life after the death of her best friend. As a result, she moves back to New York City after living in Florida for decades.
12
Mariah Carey's Magical Christmas Special (2020)
★ 6.2/10
Faced with a holiday cheer crisis, the North Pole knows there's only one person who can save the day: Santa's great friend Mariah Carey. The Queen of Christmas creates a fabulous and star-studded spectacular to make…
13
Billie Eilish - Hit Me Hard and Soft: The Tour (Live in 3D) (2026)
★ 8.4/10
Captured during Billie Eilish's sold-out world tour, a concert experience from one of the most celebrated and successful artists of her generation, presented in immersive 3D.
14
McQueen (2018)
★ 7.4/10
Alexander McQueen's rags-to-riches story is a modern-day fairy tale, laced with the gothic. Mirroring the savage beauty, boldness and vivacity of his design, this documentary is an intimate revelation of McQueen's own…
15
Avatar: The Deep Dive - A Special Edition of 20/20 (2022)
★ 7.2/10
An inside look at one of the most anticipated movie sequels ever with James Cameron and cast.
16
Honeydripper (2007)
★ 5.9/10
In 1950s Alabama, the owner of the Honeydripper juke joint finds his business dropping off and against his better judgment, hires a young electric guitarist in a last ditch effort to draw crowds during harvest time.
17
Crips and Bloods: Made in America (2009)
★ 6.6/10
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.
18
Gilbert (2017)
★ 6.7/10
The life and career of one of comedy's most inimitable modern voices, Mr. Gilbert Gottfried.
19
Newness (2017)
★ 6.1/10
In contemporary Los Angeles, two millennials navigating a social media–driven hookup culture begin a relationship that pushes both emotional and physical boundaries.
20
Chris Brown: Welcome to My Life (2017)
★ 6.4/10
This compelling Documentary moves beyond the spotlight and past the attention-grabbing headlines to give pop superstar Chris Brown a chance to tell his own story. New interviews with the international phenomenon reveal…