Robert De Nirois best known for playing some of cinema’s most iconic antiheroes and gangsters in gritty dramas about crime and the human condition. One thing that doesn’t immediately spring to mind when we think of De Niro is comedy. Yet during the past three decades of the actor’s career, in particular, some ofDe Niro’s career-defining movie roleshave 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 classicMean Streets.
In fact, it’s comedic roles that Robert De Niro apparently finds the most liberating to play. As he recently toldGQ, when acting in comedy movies “you can do things that in a straight thing you can’t do.” De Niro says he especially enjoys the “eccentric” elements that comedy brings to a character. However, although he’ll always be remembered for his dramatic performances, he’s somewhat underrated as a comic actor.De Niro’s very best moviesare mostly crime classics and personal dramas, but a fair few of them are comedies, too, which demonstrate his feel for humorous characters and storylines.

Despite its dubious premise about a mafioso renting out the services of a barmaid to a cop,Mad Dog and Gloryis one ofRobert 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 Glorytakes 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 Glorytakes 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.
Just a few years afterMad Dog and Glory,De Niro stepped into a more conventional crime role for the comedy movieAnalyze 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 theyoung Vito Corleone inThe Godfather Part II, Al Pacino inThe Untouchables, Jimmy Conway inGoodfellas, and Ace Rothstein inCasino. 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.
Probablythe only Robert De Niro comedy that’s penetrated popular consciousness to the same degree as the actor’s serious work,Meet the Parentsfeatures 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, includingMeet the Parents’ most iconic scenein 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.
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 filmsSilver Linings Playbook,American Hustle, andJoy, all feature Robert De Niro in roles with comic elements to them. His best performance of the three came inSilver Linings Playbook, for whichDe 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 comedyAmerican 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.
Wag the Dogis a forgotten gem of a Robert De Niro moviewhich 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 toarguably his most machiavellian roleof 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.

1988’sMidnight Runis the kind of crime caper thatbrings 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 inRaging Bulland Johnny Boy inMean Streets.
If this movie isPlanes, Trains and Automobilesfor thebuddy cop moviesubgenre, 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 throughoutMidnight Run’s 126 minutes.
Blink and you might missRobert 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 inBrazilis anything but.
Robert De Niro asked to play the part of Jack Lint inBrazil, 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. WhileBrazilwould still be one of thebest satirical sci-fi moviesever made on its own terms even without Robert De Niro, the actor’s role adds the cherry on top of an already lavishly layered cake of comedic brilliance.
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 hisquintessential 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 terms. 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, andRobert De Nirotreads 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 Comedyis a very funny movie about a very serious subject, which ultimately needs laughs to carry the darkness of its message across.