With Sacha Baron Cohen’s farce The Dictator about to march onto screens worldwide, it seemed a good time to look back at some of the most unforgettably loony and comical dictators seen on film. A few of these are wholly fictional but many are based loosely on real-life tyrants who made people’s lives miserable—and not in humorous ways. But through pain often comes great—if dark—comedy, as these films arguably attest.

By Craig Phillips

1. The Great Dictator

An obvious choice, yes, but absolutely essential. Chaplin’s first true talkie and biggest box office success is a brave classic in which the Little Tramp transforms himself into the Big Dictator, parodying Hitler most obviously (right during the early part of WWII) and dictators in general, masterfully. He plays both Adenoid Hynkel, and his doppelganger, a poor Jewish barber who is mistaken for the dictator. Full of tremendous moments and, in particular, two unforgettable speeches.

2. Bananas

Woody Allen's parody of Latin American/Castro-ish dictators, replete with long beards both real and fake, in which the Woodman finds himself--due to a girl, natch--enmeshed with socialist rebels who end up being just as loony as the despots they replace. (“From this day on, the official language of San Marcos will be Swedish…In addition to that, all citizens will be required to change their underwear every half-hour.”) Full of belly laughs, sight gags and silliness you won't find in most subsequent Woodys.

3. Sleeper

Woody's sci-fi comedy Sleeper also had a dictator of sorts, in a futurist Big Brother police state kind of way. The fearless leader, who appears at times in creepy pre-recorded announcements of reassurance, may or may not be still alive, but Woody as a time traveler and Diane Keaton join rebel forces and end up trying to steal the leader's nose before scientists can clone it—even though Woody assures the rebels he’s not really the heroic type, “I was beaten up by Quakers.”

4. To Be or Not To Be

There are two versions of this WWII farce, and as much as I love Mel Brooks, I prefer the 1942 Ernst Lubitsch version, with Jack Benny. It makes an excellent doubleheader with Great Dictator; a Polish acting troupe in occupied Warsaw disguise themselves as Nazis—including Benny as Hitler himself—in order to escape. Both funny and quite poignant, especially given the time it was made, and even more so considering lovely co-star Carole Lombard died in a plane crash 2 months before its release.

5. Duck Soup

Hail Freedonia! Though not entirely embraced when first released in 1933, it's now considered the Marx Brothers' greatest film, a masterpiece of political satire, a symphony of wit and slapstick. Groucho plays Rufus T. Firefly, who is appointed leader of a bankrupt nation and outsmarts and then befriends the spies Chicolini and Pinky (Chico and Harpo) before pointlessly declaring war as everything descends into hilarious anarchy. Contains much repeated mirror scene as well as many other classic gags.

6. Team America: World Police

The real-life North Korean despot Kim Jong-Il was almost a cartoon himself, if also a dangerous sociopath, and, as depicted in this puppet-toon from Trey Parker and Matt Stone, "so ronrey." The film is full of ribald satire, skewering both American machismo and politically correct celebrities, but no one comes off as memorably as Dictator Kim, who became even more world-famous after it came out.

7. You Nazty Spy

While it’s no Duck Soup, the Three Stooges’ short is pretty riotous and was the first film to openly satirize Adolph Hitler, even earlier than Chaplin’s Great Dictator. I’m no huge Stooges fan but this is a riot; sure there are terrible gags, but plenty of laughs and nyuks, too. Here, the boys are appointed, well, stooge leaders of the country of Moronica—“we’ll make this country safe for hypocrisy!”—where they mimic Hitler, Göring, Goebbels and Mussolini, before being overthrown and sent, unforgettably, to their doom (death by lion).

8. Herr Meets Hare

A classic wartime ‘toon in which Bugs Bunny squares off against both Hitler and (more prominently here) Hermann Göring, and where Bugs surprises them both by hiding in a bag dressed as Joseph Stalin (briefly our ally). Also notable as the cartoon in which Chuck Jones first tried out the Bugs-as-Brunhilde gag he’d later perfect in “What’s Opera, Doc?”; here Göring plays the Siegfried role later performed by one Elmer Fudd. Must have delighted wartime audiences (except German POWs who were made to watch it).

9. Inglourious Basterds

From Bugs to basterds (sic) in Tarantino's nutty WWII actioner, in which the most inglourious one of all is Hitler himself (Martin Wuttke), though it’s certainly a slightly… unrealistic take on der Fuhrer, with a fantasy fulfillment climax that upset those who didn't notice the rest of the film was not especially factual either. Features several memorable scenes with the dictator, including a Downfall-ish rant and a rather explosive movie screening.

10. Richard III

No, Shakespeare’s play is not a comedy, but Richard Loncraine’s ultra-clever update, set in a fictional fascist dictatorship in 1930s England, features Sir Ian McKellen’s gleeful performance that ends unforgettably with him laughing maniacally as he goes out in a blaze of glory. All the usual Bard tragedy tropes are here—murder, marriage, fratricide—but the multitalented cast (Annette Bening, Jim Broadbent, Robert Downey Jr. et al.) brings out the wit and adds a layer of bemusement to what is otherwise dark stuff.