Mafia Comedies Ranked, From Great to ‘Corky Romano’
Although Joe Pesci’s violent outbursts in Goodfellas conditioned many of us to avoid laughing at mobsters at all costs, Hollywood has cranked out numerous mafia-based comedies over the years. And thankfully, for humanity as a whole, not all of them star Chris Kattan. This gives us the opportunity to rank some of the most notable mob-based comedies, staring at the bottom with…
Kattan plays a veterinarian who goes undercover inside the FBI to help out his mobster dad, played by screen legend Peter Falk for some reason. Hilarity does not ensue. Kattan would later claim that the screenplay was punched up by There Will Be Blood director Paul Thomas Anderson, which, if true, makes us less sad for Anderson’s Best Screenplay Oscar loses.
Jane Austen’s Mafia!
Renamed simply Mafia! in order to appeal to the illiterate masses, this Godfather spoof was especially disappointing coming from director Jim Abrahams of Airplane!, Top Secret! and Hot Shots! fame. Either way, it’s by far the worst movie he made with a title ending in an exclamation point.
One of the most unnecessary sequels of all time. Surely no one needed a follow-up to Analyze This, in which Robert De Niro sings show tunes and gets a job working as a thinly veiled stand-in for The Sopranos.
Mickey Blue Eyes
A mostly harmless comedy in which Hugh Grant gets to be awkward and befuddled — but this time, it’s around a bunch of mobsters, including his soon-to-be father-in-law, played by the late great James Caan. It also featured several future Sopranos cast members, including Tony Sirico.
The Whole Nine Yards
Bruce Willis plays a mafia hitman who moves next door to Matthew Perry, which results in Perry falling down a lot. The Whole Nine Yards is a mostly enjoyable farce directed by Jonathan Lynn, who also helmed iconic comedies like Clue and My Cousin Vinny. Note: We’re not including The Whole Ten Yards on this list because we’re not 100 percent sure it actually exists.
Married to the Mob
Michelle Pfeiffer stars in Jonathan Demme’s underrated 1988 comedy, which also features Alec Baldwin, Mercedes Ruehl and Dean Stockwell. It’s not perfect, but any movie in which singer Chris Isaak plays a hitman who dresses like a Ronald McDonald-esque fast-food clown deserves to be seen by all.
The unusual pairing of Billy Crystal and De Niro made for a surprisingly great on-screen duo in Analyze This — before the joke was completely driven into the ground and buried in a shallow unmarked grave by the sequel. It may not be well thought of today, but back in 1999, Harold Ramis’ blockbuster comedy played like gangbusters (pun unavoidable).
This wildly goofy old-timey gangster parody directed by Amy Heckerling is bolstered by a great lead performance from Michael Keaton, a supporting cast that includes Danny DeVito and Peter Boyle, and a theme song by Weird Al Yankovic. While it came out in 1984, it was a cable TV staple for ’90s kids.
Vince Vaughn perfected his cringey, embarrassing sidekick character in this 2001 comedy written and directed by his co-star Jon Favreau. Two low-level goons are sent on an errand for a local mobster and nearly get killed in the process, thanks primarily to Vaughn’s incompetence. The scene in which Vaughn tries to save Favreau, armed only with a starter’s pistol, is perhaps the greatest accomplishment of his entire career.
Long before Analyze This, the original Don Corleone starred in a great comedic two-hander. Somehow, Marlon Brando was convinced to revive his Godfather persona for 1990’s The Freshman — although technically he’s playing Carmine Sabatini, who we learn served as the inspiration for the iconic character. It also stars Matthew Broderick as an NYU film student who gets roped into Carmine’s exotic animal-importing scheme after dating his daughter.
The Freshman works so well as a mafia comedy because it so perfectly combines the two genre stylings — the comedic bits are truly hilarious, while the crime drama elements feel completely authentic, thanks in large part to Brando’s willingness to commit to the ridiculous premise. The escaped Komodo dragon sequence is an all-timer.
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