Sort by Popularity - Most Popular Movies and TV Shows tagged with keywords "chicago-illinois", "gambling-debt"

1. Casino (1995)

R | 178 min | Crime, Drama

In Las Vegas, two best friends - a casino executive and a mafia enforcer - compete for a gambling empire and a fast-living, fast-loving socialite.

Director: Martin Scorsese | Stars: Robert De Niro, Sharon Stone, Joe Pesci, James Woods

Votes: 564,937 | Gross: $42.44M

2. Funny Girl (1968)

G | 151 min | Biography, Comedy, Drama

The life of Fanny Brice, famed comedienne and entertainer of the early 1900s. We see her rise to fame as a Ziegfeld girl, subsequent career, and her personal life, particularly her relationship with Nick Arnstein.

Director: William Wyler | Stars: Barbra Streisand, Omar Sharif, Kay Medford, Anne Francis

Votes: 25,208 | Gross: $58.50M

3. Hardball (2001)

PG-13 | 106 min | Comedy, Drama, Sport

A gambling addict and ticket scalper living an aimless life reluctantly agrees to coach a Little League team from the Chicago projects as part of a loan agreement.

Director: Brian Robbins | Stars: Keanu Reeves, Diane Lane, John Hawkes, Bryan Hearne

Votes: 33,410 | Gross: $40.22M

4. Dark Places (2015)

R | 113 min | Crime, Drama, Mystery

Libby Day was only eight years old when her family was brutally murdered in their rural Kansas farmhouse. Almost thirty years later, she reluctantly agrees to revisit the crime and uncovers the wrenching truths that led up to that tragic night.

Director: Gilles Paquet-Brenner | Stars: Charlize Theron, Nicholas Hoult, Christina Hendricks, Chloë Grace Moretz

Votes: 47,823

5. This Christmas (2007)

PG-13 | 117 min | Comedy, Drama, Romance

A Christmastime drama centered around the Whitfield family's first holiday together in four years.

Director: Preston A. Whitmore II | Stars: Regina King, Columbus Short, Delroy Lindo, Idris Elba

Votes: 10,452 | Gross: $49.12M

6. Al Capone (1959)

Approved | 104 min | Biography, Crime, Drama

A chronicle of the rise and fall of Chicago crime boss Al Capone during the Prohibition era.

Director: Richard Wilson | Stars: Rod Steiger, Martin Balsam, Fay Spain, James Gregory

Votes: 1,911

7. Gangster Empire: Rise of the Mob (2013– )
Episode: Chicago and the rise of Al Capone (2013)

TV-14 | 48 min | Documentary, Action, Crime

We tell the story of the rise of Al Capone and mob rule in Chicago and explore why the roaring twenties played the crucial role in gangster life and the impact of widespread police corruption.

Director: Kevin R. Hershberger | Stars: Coby Batty, Matt K. Baker, Todd Barsness, James Christopher Cooke