Movies Like Tails You Win, Heads You Lose

If you liked Tails You Win, Heads You Lose (1999), a crime and comedy movie directed by Hans-Günther Bücking, 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
Porridge (1979)
★ 6.8/10Also comedy and crime
Times are hard for habitual guest of Her Majesty Norman Stanley Fletcher. The new prison officer, Beale, makes MacKay look soft and what's more, an escape plan is hatching from the cell of prison godfather Grouty and…
2
Sauerkrautkoma (2018)
★ 7/10Also comedy and crime
When a hilariously dull policeman moves in with his best buddy in Munich, he has to deal with scandals, a corpse — and potential marriage.
3
Shadow of the Thin Man (1941)
★ 7/10Also comedy and crime
While attending a major horse race with their young son, Nick Jr., Nick and Nora Charles witnesse a shocking murder from the crowded grandstand. What first appears to be an isolated killing soon leads to a maze of…
4
How to Rob a Bank (2007)
★ 5.8/10Also comedy and crime
Caught in the middle of a bank robbery, a slacker and a bank employee become the ones who arbitrate the intense situation.
5
Hostile Takeover (2025)
★ 6.9/10Also comedy
Follows Pete, a professional hitman, as he faces a group of assassins after the boss of a crime syndicate suspects disloyalty due to his attendance at Workaholics Anonymous meetings.
6
Johnny Dangerously (1984)
★ 6.3/10Also comedy and crime
An honest, goodhearted man is forced to turn to a life of crime to finance his neurotic mother's skyrocketing medical bills.
7
The Thursday Murder Club (2025)
★ 6.6/10Also comedy and crime
A group of senior sleuths passionate about solving cold cases get plunged into a real-life murder mystery in this comic crime caper.
8
The Blue Gardenia (1953)
★ 6.5/10Also crime
Upon waking up to the news that the man she’d gone on a date with the previous night has been murdered, a young woman with only a faint memory of the night’s events begins to suspect that she murdered him while…
9
Gotcha! (1985)
★ 6/10Also comedy
A student on a trip to France is tricked into smuggling secrets across the Iron Curtain by a sexy spy.
10
Rehragout-Rendezvous (2023)
★ 6.7/10Also comedy and crime
Bavaria's most laid-back cop returns, juggling parenting and working at the family farm with the reopening of a grisly cold case.
11
Dampfnudelblues (2013)
★ 6.8/10Also comedy and crime
After the forcible transfer to his Bavarian home village, an ex-criminal cop investigates the death of a school principal who he thinks had lots to hide.
12
Analyze This (1999)
★ 6.5/10Also comedy and crime
Countless wiseguy films are spoofed in this film that centers on the neuroses and angst of a powerful Mafia racketeer who suffers from panic attacks. When Paul Vitti needs help dealing with his role in the "family,"…
13
The Limits of Control (2009)
★ 6/10Also crime
A mysterious stranger works outside the law and keeps his objectives hidden, trusting no one. While his demeanor is paradoxically focused and dreamlike all at once, he embarks on a journey that not only takes him…
14
Fabian and the Deadly Wedding (2026)
★ 6.3/10Also comedy and crime
Hapless con artist Fabian crashes a quirky winter wedding, planning to steal a valuable gift meant for the bride. But when a murder disrupts his scheme, Fabian finds himself unexpectedly drawn into solving the mystery…
15
Arsenic and Old Lace (1944)
★ 7.6/10Also comedy and crime
Mortimer Brewster, a newspaper drama critic, playwright, and author known for his diatribes against marriage, suddenly falls in love and gets married; but when he makes a quick trip home to tell his two maiden aunts…
16
Stark Raving Mad (2002)
★ 6.1/10Also comedy and crime
A crook quietly plots his revenge against the boss who murdered his brother while working for him.
17
Winterkartoffelknödel (2014)
★ 6.9/10Also comedy and crime
A policeman suspects that several bizarre deaths in the same family were murders and that the killer is a mysterious woman who just moved to the village.
18
The Dumpling Affair (2017)
★ 7/10Also comedy and crime
After a provincial policeman gets falsely accused of a crime that was committed with his pocket knife, he begins a turbulent hunt for the real murderer.
19
The Seven-Ups (1973)
★ 6.3/10Also crime
A tough detective who is part of an elite New York City unit is trying to find out who killed his partner, but uncovers a plot to kidnap mobsters for money.
20
Psych 2: Lassie Come Home (2020)
★ 7/10Also comedy and crime
After Santa Barbara Police Chief Carlton Lassiter is ambushed and left for dead, Shawn and Gus return to help him and find themselves embroiled in a case involving the personal, the professional – and even the…