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There’s an old Hollywood adage that’s ascribed to plenty of famous actors, although it’s most famously uttered by Peter O’Toole’s beleaguered actor in the 1982 film My Favorite Year: “Dying is easy. Comedy is hard.” It cuts to the quick of the seemingly bifurcated nature of acting: you’re either a dramatic one, or a comedy one — and one is definitely easier to pull off than the other. For Oscar winner Robert De Niro, it’s easy to see which one he fits considering his monumental, iconic roles as brooding, intense tough guys in movies like The Godfather Part II, Taxi Driver, The Deer Hunter, and Goodfellas, among others. But he’s refused to allow himself to be typecast, turning up in plenty of comedic roles throughout his five-decade film career.

With Nancy Meyers’ latest comedy The Intern, which sees De Niro heading back into the workforce as the 70-year-old intern to Anne Hathaway’s fashion entrepreneur, opening in theaters on Friday, it’s worth examining how well De Niro fares in lighter fare… which is to say, it’s always a gamble.

Like most accomplished, serious actors, it’s always a unsettling sight to see Robert De Niro in a true screwball comedy — which is why it happens so infrequently. And oh, if only it hadn’t. His appearances in disasters like The Adventures of Rocky & Bullwinkle (as Boris and Natasha’s boss, Fearless Leader), the Hollywood satire What Just Happened, or Last Vegas (the old dude version of The Hangover) were regrettable mistakes, but they aren’t the only clunkers on his filmography. There’s also dysfunctional family comedies like Everybody’s Fine and The Big Wedding, plus a few dim-witted sequels to surprising comic hits.

Analyze This and Meet the Parents were both surprising films for De Niro, two honest-to-goodness comedies that featured plenty of pratfalls and sight gags. But the reason why De Niro was so good in them is because he was playing the straight man to a more seasoned comic pro (Billy Crystal and Ben Stiller, respectively) who got the flashy, funny role. De Niro, instead, was basically parodying himself; in Analyze This, he played a neurotic, overemotional mobster, while in Meet the Parents he played an ex-CIA agent who uses some of his old tricks to intimidate and interrogate his daughter’s fiancé. To see De Niro essentially play to type, albeit in a film with a lighter tone, definitely worked. (The sequels, however — Analyze That, Meet the Fockers, and Little Fockers — are questionable.)

This isn’t to say that De Niro can’t handle a comic role, but rather it’s harder for us to accept in one. That’s why his best comedies often find him playing a particularly complicated, damaged character. While Martin Scorcese’s The King of Comedy isn’t necessarily a funny film, De Niro shines as an aspiring stand-up comic who spends more time stalking his idol (played by Jerry Lewis) than he does telling any jokes. In the political satire Wag the Dog, De Niro plays, again, a gruff, brutal man: a Hollywood producer tasked with faking a European conflict to distract America from a presidential sex scandal. He earned an Oscar nomination for David O. Russell’s romantic comedy Silver Linings Playbook, but that role definitely veers more on the dramatic end of the spectrum.

His funniest role to date might also be one of his most underrated: as the bumbling, incredibly stupid ex-con Louis Gara in Quentin Tarantino’s quick-witted caper, Jackie Brown. De Niro does so much with a character that has little to do, and it’s a truly phenomenal supporting performance — one that paled in comparison to showier performances from his scene partners in Samuel L. Jackson and Bridget Fonda, both playing (only slightly) smarter characters who manage to foil Louis’ schemes.

You have to give De Niro credit for trying, of course, because failing at comedy is a much more excruciating feat than failing at drama. He’s done it well enough that it makes me forgive him for all of the blunders — for instance, nearly every time he has appeared on Saturday Night Live. He’s hosted the three times and showed up as a guest star four more times, and, bless his heart — I can never figure out why he keeps coming back, because he always looks like he’s having the worst time. But maybe that’s also why it works. It’s almost impossible not to see a little bit of Travis Bickle, Jake LaMotta, or Jimmy Conway in him whenever he turns up on screen, and it’s doubly hilarious to think of those guys trying to read dick jokes off of a cue card while keeping a straight face.

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Photos: Everett Collection