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Robert De Niro is a legendary cinema star who is regarded as one of the finest actors of his generation, with a career spanning over five decades. Though he is known for portraying tough guy characters with a penchant for danger and mayhem, he has continually surprised and delighted audiences with more humorous roles in hit films like Analyze This and Meet the Parents. From bounty hunters to notorious Washington D.C. fixers, and a delusional wannabe stand-up comedian, De Niro is not afraid to embrace his funny side.
In recent years, the actor has continued to zig instead of zag by taking on sidesplitting characters in the raunchy comedy Bad Grandpa and dramedies such as The Comedian and The Intern. De Niro is set to star in two upcoming comedy-related projects, About My Father and Inappropriate Behavior. Let’s take a look at some of Robert De Niro’s best comedy movies.
9/9 We’re No Angels
Robert De Niro appears alongside Sean Penn in the 1989 comedy We’re No Angels, a remake of the classic ’50s flick in which the talented duo portray two escaped convicts who in an effort to cross the border to Canada pose as priests and hideout in a monastery to evade authorities.
Set during the 1930s Great Depression, Ned (De Niro) and Jim (Penn) take a shot at finding their freedom when they are inadvertently dragged into a prison escape by a deranged serial killer; as they pretend to keep up their priest guise in Canada, Ned finds himself falling for a stunning local girl (Demi Moore). The film features hilarious performances by the cinema superstars but failed to resonate with audiences like the original picture did.
8/9 Brazil
De Niro stars as an outlaw heating engineer and wanted terrorist in the 1985 dystopian dark comedy Brazil, telling the wondrous tale of a perpetually daydreaming man (Jonathan Pryce) in a futuristic society who pursues the woman of his dreams and is caught up in a dangerous conspiracy by the government. Terry Gilliam directs the satiric fantasy, parodying topics like hyper-surveillance and state capitalism and drawing inspiration from George Orwell’s lauded sci-fi dystopian masterpiece Nineteen Eighty-Four. De Niro’s straight-man performance in an exciting and absurd world makes the satire that much more enjoyable, as he expertly showcases his comedic capabilities.
7/9 Mad Dog and Glory
Touting a sensational cast led by De Niro, Uma Thurman and Bill Murray, the 1993 crime dramedy Mad Dog and Glory centers on shy crime scene photographer Wayne “Mad Dog” Dobie, who after saving the life of notorious mob boss Frank Milo (Murray) is given the company of a beautiful waitress for a week as repayment; their situation becomes far more complicated when the pair fall in love and Milo demands back what is “his.”
De Niro’s portrayal of a mild and meek man hounded by the mob was a fun change of pace for the actor, who is often the character that is powerful and feared. The New York Times wrote, “The great satisfaction of Mad Dog and Glory is watching Mr. De Niro and Mr. Murray play against type with such invigorating ease.”
6/9 Greetings
In his first major cinematic role, De Niro portrays an aspiring director with peeping tom tendencies in the 1968 black comedy Greetings, telling three different stories focused on a trio of New York friends that satirizes topics of the time like free love and the Vietnam War. Directed by Brian De Palma, the farce was shown at the Berlin International Film Festival where it went on to win the prestigious Silver Bear award and was lauded by critics; the comedy also marks the first of a series of collaborations between De Palma and De Niro, who would go on to work together in movies like The Untouchables and the well-received Greetings sequel Hi, Mom!.
5/9 Analyze This
When infamous gangster Paul Vitti finds himself plagued by panic attacks brought on by a failed assassination attempt, he enlists the services of a weary psychiatrist to help him in the 1999 mafia comedy Analyze This. Comedian extraordinaire Billy Crystal portrays the reluctant doctor tasked with “fixing” the deep rooted issues of De Niro’s Vitti in the Harold Ramis hit, which was both a critical and commercial hit and grossed over $176 million.
De Niro and Crystal’s undeniable chemistry earned widespread praise by critics, with the Chicago-Sun Times commending the flick and noting, “Funny partly because De Niro and Crystal do what we expect them to do, and partly because they don’t.” The success of Analyze This led to the 2002 sequel Analyze That.
4/9 Meet the Parents
Robert De Niro and Ben Stiller hilariously face off in the 2000 blockbuster hit Meet the Parents, in which the silver screen legend appears as a war vet and retired CIA agent who instantly dislikes his daughter’s new boyfriend, who plans to propose upon earning his blessing.
Director Jay Roach sought out the actor to star in the comedy after his lively roles in Analyze This and The Adventures of Rocky and Bullwinkle, and De Niro’s performance was singled out in the picture; on working with Goodfellas star, Stiller stated that “it was a little bit intimidating working with De Niro” but that he “has a great sense of humor and I think that’s the biggest surprise about him.”
3/9 Wag the Dog
In Barry Levinson’s 1997 Oscar-nominated black comedy Wag the Dog, De Niro is a savvy Washington D.C. spin doctor who devises a ploy to cover the president’s sex scandal with the help of a influential Hollywood producer, doing so by creating a fictional war. The actor is joined on screen by Dustin Hoffman and Anne Heche in the political satire, which generated popularity and publicity due to the Clinton-Lewinsky scandal that hit a month after its release.
Wag the Dog landed on numerous critics top lists including The Washington Post’s ranking of the best political movies ever made; it also went on to win the Special Jury Prize at the Berlin International Film Festival.
2/9 The King of Comedy
De Niro was absolutely brilliant as a delusional struggling stand-up comic with dreams of making it big in the 1982 satirical black comedy The King of Comedy, following his character Rupert Pupkin as he stalks and ultimately kidnaps his funnyman idol and famous late-night host Jerry Langford (Jerry Lewis). The Martin Scorsese masterpiece King of Comedy features a tour de force performance by De Niro, whose delivery of the well-meaning but mentally unstable Rupert showcased his comedic prowess early in his career; the actor spent months studying stand-up comedians in order to get his rhythm and delivery right for the challenging role.
Despite failing to make waves upon its initial release, The King of Comedy has since gone on to amass a cult following and has since earned a reputation as one of Scorsese’s greatest films. The director himself called De Niro’s role as Rupert Pupkin his favorite of their collaborations.
1/9 Midnight Run
Robert De Niro and Charles Grodin are a pair of mismatched misfits in the sidesplitting 1988 buddy cop comedy Midnight Run, in which the former portrays gifted bounty hunter Jack Walsh, who is tasked with capturing a mob accountant that is also being sought after by everyone from dangerous criminals to the FBI. Jack finds himself dodging mobsters and the authorities on his cross-country quest with the erratic Jonathan “The Duke” Mardukas, with uproarious hijinks ensuing.
Midnight Run went on to earn De Niro a Golden Globe nomination for Best Actor and was a smash hit with both audiences and critics, with Roger Ebert declaring, “Whoever cast De Niro and Grodin must have had a sixth sense for the chemistry they would have; they work together so smoothly, and with such an evident sense of fun, that even their silences are intriguing.”
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