6 Gangster Comedies That Are Worth Watching - Spotflik 6 Gangster Comedies That Are Worth Watching - Spotflik
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6 Gangster Comedies That Are Worth Watching

Sep. 12. 2021

Wise Guys (1986)

In addition to suspense thrillers, Brian De Palma has made some of the most popular crime dramas of their respective decades, including ‘Scarface’, ‘The Untouchables’, and ‘Carlito’s Way.’ It’s probably not surprising that he tackled the mafia comedy genre in “Wise Guys,” one of his lesser-known but rather lovely comedies.

The film follows Henry Valentini (Danny DeVito) and Moe Dickstein (Joe Piscopo). Their friendship dates back to childhood. In addition to taking laundry for mobster gangsters, these men also work for mobster gangsters. Their boss always puts money on the same horse and always loses. One day they’re supposed to place an order. When they bet on the supposed favorite, things go wrong, they lose, and now they’re being killed. What follows is a lot of situation comedy. An old-school comedy, a bit over-the-top at times, but still lighthearted. You find the lead characters sympathetic and root for them. There is a great ending as well. This movie has authentic New Jersey locations and Harvey Keitel gives a classy performance, his only appearance in a De Palma film. The Springsteen love De Palma shows in one fine sequence.

Mickey Blue Eyes (1999)

Strangely, this one got mixed reviews. Despite it being nothing special, it’s not the kind of film that you’d necessarily criticize for plot holes or lack of creativity in the premise. It’s not a film that claims to have some smart premise or original storyline; whether the humor works for you is another topic. It has a lot of ‘90s charm, and it didn’t age badly.

Similar to his role in “Four Weddings”, Hugh Grant plays a British gentleman who falls in love with an American woman who is the daughter of a gangster. He puts himself in all of these situations and then makes us laugh. That’s the premise. “The Gentlemen” shows Grant’s comic timing, but it’s entirely different from his gangster role in “Grant’s Gift.” Another funny actor here is James Caan, who starred in “The Godfather.” 

Despite getting a lot of TV airings in some countries, this film flopped at the box office, possibly because “Analyze This” was very fresh on the minds of people and they didn’t want to see another gangster comedy so soon.

The Freshman (1990)

As a new student at the New York film school, a mafia family elevates him to a key role in an elaborate game about rare animals, questionable specialty restaurants, wildlife protection, and fake FBI agents. In an interview with “Inside the Actors Studio”, James Caan once claimed that his performance of “Mickey Blue Eyes” was also a parody of the Godfather.

“The Freshman,” however, is a brilliant parody of Marlon Brando’s “Godfather” performance. Even with limited screen time, he has a rare chance to actually be funny. Despite that, it’s still a pretty fun film. One wonders what happened to director/writer Andrew Bergman, who wrote another rom-com around that time called “Honeymoon in Vegas.” Is that what it’s all about? Why? Our goal is to have fun, and the ride is certainly enjoyable. The film benefits from Matthew Broderick’s charming lead performance as well as his emotional honesty.

Johnny Dangerously (1984)

The director of “Fast Times at Ridgemont High” and “Clueless” has created two of the most popular teen comedies of all time, but her attempt at gangster comedy is underrated and is everything you would expect from a film like this. Michael Keaton gives a great performance as an honest man who goes to the dark side to pay his mother’s bills in this charming homage to 1930s gangster films. If you’re familiar with films from the 1930s and 1940s, like “Scarface,” “Manhattan Melodrama,” “White Heat,” and “Public Enemy,” then the film becomes even funnier.

Keaton is great, but the supporting cast is great as well, with some truly funny characters. There are a lot of fine one-liners and witty jokes. The pacing is fast. Because this actually seems like a Mel Brooks movie, it’s no wonder Mel Brooks referenced it in his “Robin Hood” parody. Although there are some outdated moments and the film feels more like a series of gags than an actual movie, it’s a lot of fun if you’re in the mood for it.

 My Blue Heaven (1990)

In those days, gangster films were very common. “Goodfellas” and “King of New York” were 1990’s cult hits, and here we have a movie that actually is a fine companion piece to those movies (as strange as it sounds), since both movies are about Henry Hill. Nora Ephron and Nicholas Pileggi, the couples behind the films, were married.

Ephron’s screenplay, on the other hand, takes a completely different route. Steve Martin plays the main character who is in witness protection. Rick Moranis portrays our other main character, the FBI agent, who lives in the suburbs and is not planning to leave crime behind. Moranis and Joan Cusack’s storyline feels more realistic to the film’s tone, while Martin’s performance is amusing, but not one of his best. Despite being released just a few weeks before “Goodfellas,” this is a witty and funny film.

6 Gangster Comedies That Are Worth Watching

A total pop culture junkie who loves watch watching Thelma and Louise over and over again.Suffering from severe OCD- that is obsessive coffee disorder.