Tails You Win, Heads You Lose (1999): cast, story & where to watch
1999 · Film · ★ 5.1

Released in 1999, Tails You Win, Heads You Lose is a comedy and crime film directed by Hans-Günther Bücking, running about 90 minutes.
What it’s about. Two beautiful young women kill men in a villa in Tuscany: Maya and Cora have been friends since childhood. Maya has an alcoholic artist father who deserted the family, a mentally disturbed mother and a violent brother, Carlo. Cora is from a wealthy middle-class family. Cora helps Maya to poison Carlo's friend Detlef, who is threatening to blackmail her. They then kill Carlo when he tries to rape Cora. Cora's family takes Maya in, and a happy time begins for her, particularly when they spend the summer in Italy.
Who’s in it. Tails You Win, Heads You Lose stars Heike Makatsch as Maja, Christiane Paul as Cora, Andrea Eckert as Anna and Helmut Berger as Henning, among others.
How it landed. With an audience score of 5.1/10, Tails You Win, Heads You Lose has proved divisive with audiences.
Where to watch. Streaming options change often. See the full, country-by-country breakdown on our where to watch Tails You Win, Heads You Lose page.
If you liked it. Fans of Tails You Win, Heads You Lose tend to enjoy Forrest Gump, Parasite, Life Is Beautiful and Fight Club.
Frequently asked
- Where can I watch Tails You Win, Heads You Lose (1999)?
- Streaming, rental and purchase options for Tails You Win, Heads You Lose change frequently. Check our where-to-watch page for the latest availability in your country.
- Is Tails You Win, Heads You Lose worth watching?
- Tails You Win, Heads You Lose holds an audience score of 5.1 out of 10, and is a strong pick if you enjoy comedy and crime. Reactions are mixed, so it may depend on taste.
- Who stars in Tails You Win, Heads You Lose?
- Tails You Win, Heads You Lose stars Heike Makatsch, Christiane Paul, Andrea Eckert, Helmut Berger and Stephan Luca.
- When was Tails You Win, Heads You Lose released?
- Tails You Win, Heads You Lose was released in 1999, with a runtime of about 90 minutes.
