Robert De Niro’s best curmudgeon roles

Few superstars have had careers as long and wide-ranging as the American actor Robert De Niro. From his early, iconic roles in classic films like Raging Bull, Heat, and The King of Comedy, to his more recent comedic parts where he’s really let his “old man yells at cloud” side shine, he’s done everything and then some. With the upcoming release of About My Father, another comedy where he plays a curmudgeonly older character, we were wondering what the best late, funny De Niro films and television appearances might be, and have come up with the below list. If you want to know what we think the best Robert De Niro curmudgeon roles are, then read ahead!

10. 30 Rock

De Niro’s brief performance in season five’s “Operation Righteous Cowboy Lightning” was astoundingly funny, even for a show known for its comedic brilliance. The episode follows Jack (Alec Baldwin) as he tries to plan ahead for celebrity-led benefit events for natural disasters, as he believes they get the strongest ratings. This leads to him asking De Niro to prepare lines for varying disasters, from wildfires, to floods, to the “wonderful flood that put out that devastating wildfire.” Although he only cameos for around a minute, pretty much every line is perfectly delivered with the right mix of deadpan and patheticness, as De Niro realizes just how much of his time he’s wasting.

9. Dirty Grandpa

While this film is truly, truly terrible, De Niro is a bright spot, delivering his awfully written lines in a way that makes them seem both believable and funny. The movie follows lawyer Jason (Zac Efron) as he drives his perverted grandfather Dick (De Niro) to Boca Raton in Florida, as a result of Dick’s license being suspended. Although initially uneasy, Jason agrees to take the old man south from Georgia, even though he is getting married to his controlling fiancee in a few days. On the trip, there are plenty of raunchy, drug-fueled hijinks, as well as a fair amount of innuendo to go along with it. Tired, bawdy in the worst ways, and a little bit dull at points, Dirty Grandpa is only worth it for De Niro’s ability to turn toilet humor into something resembling gold.

8. The War with Grandpa

Nothing says “curmudgeonly” quite like getting in a prank war with your own grandchild over a bedroom, yet that’s the offbeat plot of this surprisingly inadequate movie led by a cast of some of Hollywood’s best. De Niro plays the granddad who has to move back in with his daughter (Uma Thurman) after he has a mishap with a self-checkout machine (ageism, check). However, he’s moved into his grandson Peter’s (Oakes Fegley) room, which the young man is not the biggest fan of. Thus begins the prank war, and it’s as ridiculous as you’d expect. Like Home Alone but with lower stakes and much less charm, De Niro is one of the few bright spots, making his unconvincing character seem not just real, but worthy of empathy.

7. Extras

Like many guest stars on this iconic Ricky Gervais comedy, De Niro plays an exaggerated version of himself when appearing on Extras, and, boy, is he hilarious, despite only having a few scenes in the second season episode he appears in. The Raging Bull actor is seen waiting for Andy (Gervais) alongside Darren (Stephen Merchant). As the Hollywood star begins getting annoyed at Andy’s tardiness, Darren distracts him with a pornographic pen, which De Niro becomes enchanted by. Eventually, the pair go out for drinks, which Andy joins them in, leading to more hilarity. A great, hilarious cameo.

6. Amsterdam

This slick, well-casted political comedy thriller could have been a real hit if it had played its cards right, but sadly, Amsterdam tried to fit too much into what could have been a very relevant tale given the state of our world, and was only really held together by some great performances, including De Niro’s. He plays General Gil Dillenbeck, a stand-in for Smedley Butler, who testified before the McCormack–Dickstein committee in 1934 about a group of business leaders who planned to have FDR removed in a coup and replaced with a Fascist (and therefore more “business-friendly”) leader. While the plot of Amsterdam didn’t have to exactly match the details of “the business plot,” as it was known, the way the story links in is too much of a stretch to support the rest of the film. It’s a shame, though, because De Niro is great in it.

5. Everybody’s Fine

This 2009 American remake of an iconic 1990 Italian classic of the same name has De Niro playing Frank, a recently widowed man who’s waiting for his kids to come and visit him. As each of them cancels for various reasons, he decides to plan a road trip to visit them all instead, and in the process, opens up old fights while maybe healing some even older wounds. Although this doesn’t quite have the humor of some of the other entries on this list, De Niro manages to portray both Frank’s cranky and sensitive side, showing his range as he delves into themes of loneliness and regret. Curmudgeonly? Yes. Poignant? That too.

4. Shark Tale

De Niro went back to his mob movie roots but in a more lighthearted way in this animated classic. Shark Tale follows the story of Oscar (Will Smith), a bit of a loser who claims to have killed the son (Lenny, voiced by Jack Black) of a shark mob boss (De Niro) so people will start to consider him a hero. Oscar and Lenny then team up to make sure everyone believes the crime happened, so they can both live in peace as Lenny is a vegetarian who doesn’t want to follow in his father’s footsteps. Unsurprisingly, De Niro is great in this role, managing to bring his unique brand of fear in parts while also balancing the need to be funny. A brilliant movie, made even better by the veteran actor’s performance.

3. Flawless

Another poor film that’s buoyed solely by star performances, De Niro is genuinely incredible in this 1999 crime comedy about a former security guard named Walt (De Niro) who suffers a stroke, and as a result ends up getting close to his one-time antagonistic neighbor, a drag queen named Rusty (Philip Seymour-Hoffman). It’s a real shame that the film itself doesn’t hit the high notes it could thanks to a confused script and misguided storyline, because the performances from its male leads are genuinely astounding, toeing the line beautifully between heartbreaking and hilarious.

2. Meet the Parents

Playing the grouchy, old dad who hates his daughter’s boyfriend, De Niro puts in a sparkling comedic performance in this 2000 remake of the 1992 independent classic, updated to include a lot more star power. Alongside De Niro, the cast includes Ben Stiller and Owen Wilson, and they, plus their fellow actors, turn this slapstick piece into something a lot more heartfelt and interesting. De Niro is in natural territory as an overprotective former CIA agent who suffers from bouts of paranoia, but he manages to massage the comedic elements out of his character instead of the darker ones, matching the tone of the film. Two sequels came from the movie, but the first remains the best.

1. Analyze This

Not quite The Sopranos in terms of drama, this mafia comedy about a mob boss who goes to see a shrink is vintage curmudgeonly De Niro, blending his old man anger with his brilliant comedic timing and ability to play the straight man. He plays Paul, a mafia boss who begins having panic attacks and has to see a psychiatrist named Ben (Billy Crystal). Through a series of mishaps and misunderstandings, the pair become more entwined in each other’s lives, leading to Ben taking a bullet for Paul. Funny, smart, and showing De Niro at his wonderful best, this is a great watch that puts a spin on the odd-couple comedy trope.