De Niro's career-defining movie roles have been primarily comedic. De Niro has a highly-developed comic sensibility that first became evident when he played unruly small-time criminal "Johnny Boy" Civello in Martin Scorsese’s 1973 classic Mean Streets.

In fact, it’s comedic roles that Robert De Niro apparently finds the most liberating to play. As he recently told De Niro’s very best movies are mostly crime classics and personal dramas, but a fair few of them are comedies, too, which demonstrate his feel for humorous characters and storylines.

8 Mad Dog and Glory

1993

Despite its dubious premise about a mafioso renting out the services of a barmaid to a cop, Mad Dog and Glory is one of Robert De Niro’s best forays into comedy gangster movies, mostly because of how self-aware the movie is. Its sense of humor is best encapsulated by a scene in which De Niro gives Bill Murray, who’s playing an Italian-American mob boss, advice about his approach to stand-up comedy.

Mad Dog and Glory takes its own advice to hilarious effect, with Robert De Niro turning the tables on the kind of character he would typically play in a more serious mobster movie.

The wonderful irony of this scene is summed up by the line, “Sometimes you should aim in, you know, make a joke at your own expense.” Mad Dog and Glory takes its own advice to hilarious effect, with De Niro turning the tables on the kind of character he would typically play in a more serious mobster movie.

7 Analyze This

1999

Just a few years after Mad Dog and Glory, De Niro stepped into a more conventional crime role for the comedy movie Analyze This. The film follows the ordeal of Billy Crystal’s psychiatrist, Dr. Ben Sobel, who unexpectedly finds himself treating mob boss Paul Vitti against his will.

De Niro hams up his performance of Vitti to the maximum, playing an over-the-top version of the roles we’ve come to associate with him through parts like the young Vito Corleone in The Godfather Part II, Al Pacino in The Untouchables, Jimmy Conway in Goodfellas, and Ace Rothstein in Casino. What results is a bellyachingly funny comedy of misunderstandings, as Ben tries to get Paul in touch with his feelings, while Paul drags Ben into the deep end of his criminal underworld.

6 Meet the Parents

2000

Probably the only Robert De Niro comedy that’s penetrated popular consciousness to the same degree as the actor’s serious work, Meet the Parents features one of the actor’s most beloved roles. He leans into his status as an aging star to gruff and fiercely protective family patriarch Jack Byrnes, whose prospective son-in-law Greg Focker, played by Ben Stiller, can’t help but make a catastrophic mess of a weekend with his future family.

De Niro added his own touches to the role, including Meet the Parents’ most iconic scene in which Byrnes gives Focker a lie detector test using the antique polygraph machine hidden in a secret room in his house. There are some big laugh-out-loud moments in this modern classic, invariably provided by the heavy-handed reactions of De Niro’s Byrnes to the cringeworthy comic blunders committed by Stiller’s character.

5 American Hustle

2013

For a brief moment in the mid-2010s, David O. Russell was able to bring together some of the world’s biggest movie stars to work together in successive movies. His films Silver Linings Playbook, American Hustle, and Joy, all feature Robert De Niro in roles with comic elements to them. His best performance of the three came in Silver Linings Playbook, for which De Niro received his seventh Oscar nomination. However, this performance is more moving than it is funny.

De Niro’s funniest role in a David O. Russell movie is unquestionably his turn as fictional mafia boss Victor Tellegio in the 2013 black comedy American Hustle. The actor’s surprisingly convincing command of Arabic steals one of the movie’s funniest scenes, in which Richie DiMaso’s sting operation almost comes crashing down in the most dangerous possible circumstances.

4 Wag the Dog

1997

Wag the Dog is a forgotten gem of a Robert De Niro movie which sees him step right out of his comfort zone to play a political spin doctor. A razor-sharp satire that accidentally predicted the events that would envelop the final years of Bill Clinton’s US presidency, the film brings together De Niro and Dustin Hoffman as characters conspiring to distract the American public from a personal scandal in the top office of the United States.

Wag the Dog’s plot might cut a little close to the bone for some, but it seems even more relevant in retrospect than when it was first released in 1997.

Here, De Niro applies the self-assured cynicism and unscrupulous scheming of his better-known mafia characters to arguably his most machiavellian role of the lot. As his character, Conrad Brean, says at one point in the movie, “War is showbusiness.” Wag the Dog’s plot might cut a little close to the bone for some, but it seems even more relevant in retrospect than when it was first released in 1997.

3 Midnight Run

1988

1988’s Midnight Run is the kind of crime caper that brings out the best in Robert De Niro as an actor, exploring the full breadth of his emotional range. On the face of it, the movie sees De Niro playing against type as likable but hot-tempered bounty hunter Jack Walsh. On the other hand, his role relies on the kind of explosive energy that De Niro brought to his portrayal of Jake LaMotta in Raging Bull and Johnny Boy in Mean Streets.

If this movie is Planes, Trains and Automobiles for the buddy cop movie subgenre, then Robert De Niro is the perfect actor to play a hard-boiled version of Steve Martin’s character in the John Hughes family comedy. The camaraderie between De Niro’s Walsh and Charles Grodin’s character Jonathan "The Duke" Mardukas feels genuine, too, which helps add emotional depth to the humor that comes in spades throughout Midnight Run’s 126 minutes.

2 Brazil

1985

Blink and you might miss Robert De Niro’s scarcely-believable cameo as Harry Tuttle in Terry Gilliam’s black comedy masterpiece, Brazil. De Niro plays a balaclava-clad vigilante plumber who escapes a torturous death at the hands of the movie’s totalitarian bureaucracy by virtue of a typo in its opening scene. If that sounds bleak, then De Niro’s brief appearance in Brazil is anything but.

Robert De Niro asked to play the part of Jack Lint in Brazil, but Terry Gilliam had already cast Michael Palin in the role, so created the part of Harry Tuttle specifically for De Niro.

It’s a joy to watch De Niro somehow make this hilariously absurd part his own, playing the Robin Hood of ducts in a dystopian world where even the most basic household repairs are stifled by the heavy hand of the law. He even abseils down a zip wire under cover of the night once his work is done. While Brazil would still be one of the best satirical sci-fi movies ever made on its own even without Robert De Niro, the actor’s role adds the cherry on top of an already lavishly layered cake of comedic brilliance.

1 The King of Comedy

1982

Robert De Niro might not be best known for (or as) The King of Comedy, but this cult Martin Scorsese movie is certainly his best comic performance. De Niro’s character Rupert Pupkin is effectively another side of his quintessential antihero, Taxi Driver’s Travis Bickle. Both characters are fundamentally driven by the desire to overcome a sense of alienation and loneliness they feel through means which appear to be beyond their grasp in conventional . Their inability to handle their feelings leads them to commit criminal acts that could cause untold harm to those from whom they’re seeking validation.

Rupert Pupkin is a wannabe comedian with a very dark side, and Robert De Niro treads the blurred line between the character’s comic aspirations and his deluded and dangerous actions beautifully. This is a jet black comedy, but its piercing humor gets to the heart of the desperation that motivates Pupkin and his equally delusional sidekick. What’s more, Jerry Lewis works superbly playing a version of himself, Pupkin’s hero Jerry Langford. The King of Comedy is a very funny movie about a very serious subject, which ultimately needs laughs to carry the darkness of its message across.